UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of

the Securities Exchange Act of 1934

(Amendment No.  )

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LEAFLY HOLDINGS, INC.

(Name of Registrant as Specified In Its Charter)

(Name of Person(s) Filing Proxy Statement, if Other Than the Registrant)

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Notice of 2025 Annual Meeting of Stockholders and Proxy Statement

ANNUAL MEETING

Wednesday, June 11, 2025 9:00 a.m. Pacific Time

Online Meeting Only – No Physical Meeting Location

LEAFLY HOLDINGS, INC.

600 1st Ave, Suite 330, PMB 88154

Seattle, WA 98104-2205

Dear Stockholder:

On behalf of our Board of Directors, I cordially invite you to participate in the 2025 Annual Meeting of stockholders (the “Annual Meeting”) of Leafly Holdings, Inc. (“Leafly” or the “Company”), to be held on Wednesday, June 11, 2025, at 9:00 a.m. Pacific Time.

We will hold our Annual Meeting in a virtual only format, which will be conducted via a live webcast. You will be able to participate in the Annual Meeting, vote your shares electronically and submit questions during the meeting by visiting http://www.virtualshareholdermeeting.com/LFLY2025 and using the control number which appears on your Notice of Internet Availability of Proxy Materials. The stockholders of the Company (the “Stockholders”) will have an equal opportunity to participate in the Annual Meeting online regardless of their geographic location.

The attached Notice of Annual Meeting of Stockholders and Proxy Statement contain details of the business to be conducted at the Annual Meeting and the procedures for participating, submitting questions and voting at the virtual meeting.

Whether or not you attend the Annual Meeting, it is important that your shares be represented and voted at the meeting. Therefore, we urge you to promptly vote and submit your proxy via the Internet, by phone or by mail.

On behalf of the Company’s Board of Directors, we would like to express our appreciation for your continued support of and interest in Leafly.

Sincerely,

/s/ Yoko Miyashita

Yoko Miyashita

Chief Executive Officer

LEAFLY HOLDINGS, INC.

600 1st Ave, Suite 330, PMB 88154

Seattle, WA 98104-2205

other information about the Company is contained in our Annual Report on Form 10-K for the fiscal year ended December 31, 2024, as filed with the Securities and Exchange Commission (the “SEC”) on March 31, 2025.

YOUR VOTE IS VERY IMPORTANT TO US. Whether or not you plan to virtually attend the Annual Meeting, we strongly encourage you to vote by Internet, by phone or by signing, dating and returning your proxy card at your earliest convenience. Sending in your proxy card will not prevent you from voting your shares at the Annual Meeting, if you desire to do so.

Stockholders may vote their shares at www.proxyvote.com, by telephone or by mail, prior to the virtual Annual Meeting or at http://www.virtualshareholdermeeting.com/LFLY2025 during the virtual Annual Meeting.

IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE VIRTUAL ANNUAL MEETING TO BE HELD ON JUNE 11, 2025. Our proxy materials, including the Proxy Statement and Annual Report, are available at the following websites: https://investor.leafly.com and http://www.virtualshareholdermeeting.com/LFLY2025.

By Order of the Board,

/s/ Yoko Miyashita

Yoko Miyashita

Chief Executive Officer and Secretary

TABLE OF CONTENTS

Forward-Looking Statements

This Proxy Statement contains a number of forward-looking statements. All statements, other than statements of present or historical fact included in this Proxy Statement regarding our future financial performance, strategy, operations, operating results, financial position, estimated revenues, losses, projected costs, prospects, plans and objectives of management are forward-looking statements. Words, and variations of words, such as “may,” “expect,” “anticipate,” “believe,” “intend,” “plan,” “will,” “could,” “should,” “would,” “predict,” “potential,” “can,” “designed,” “seek,” “strive,” “opportunities,” and “continue” and similar expressions are intended to identify our forward-looking statements. You should read statements that contain these words carefully because they:

You are cautioned not to place undue reliance on these forward-looking statements, which speak only as of the date of this Proxy Statement.

All forward-looking statements included herein are expressly qualified in their entirety by the cautionary statements contained or referred to in this section. Except as noted below, these cautionary statements are being made pursuant to federal securities laws with the intention of obtaining the benefits of the “safe harbor” provisions of such laws. Except to the extent required by applicable laws and regulations, Leafly undertakes no obligations to update these forward-looking statements to reflect events or circumstances after the date of this Proxy Statement or to reflect the occurrence of unanticipated events.

There may be events in the future that Leafly is not able to predict accurately or over which it has no control. The sections in our Annual Report for the fiscal year ended December 31, 2024 entitled “Business,” “Risk Factors,” “Management’s Discussion and Analysis of Financial Condition and Results of Operations,” and the other cautionary language discussed in this Proxy Statement provide examples of risks, uncertainties and events that may cause actual results to differ materially from the expectations described by Leafly in such forward-looking statements.

Because the Transaction (as defined below) is a “going private” transaction within the meaning of Rule 13E-3 under the Exchange Act, the forward-looking statements contained in this proxy statement made in connection with the Transaction are excluded from the safe harbor protection provided by the Private Securities Litigation Reform Act of 1995 and Section 27A of the Securities Act of 1933, as amended.

SUMMARY TERM SHEET

This summary term sheet highlights selected information from this Proxy Statement about the proposed Transaction. This summary term sheet may not contain all of the information that is important to you. For a more complete description of the Transaction, you should carefully read this Proxy Statement in its entirety. For your convenience, we have directed your attention to the location in this Proxy Statement where you can find a more complete discussion of each item listed below.

As used in this Proxy Statement, the term “Transaction” refers, collectively, to the Reverse Stock Split (as defined below) and subsequent purchase of fractional shares, each as discussed below.

The Transaction is considered a “going private” transaction as defined in Rule 13e-3 promulgated under the Exchange Act because it is intended to, and, if completed, will enable us to, terminate the registration of (or “deregister”) our common stock under Section 12(g) of the Exchange Act and suspend our duty to file periodic reports and other information with the SEC under Section 15(d) of the Exchange Act. In connection with the Transaction, we have filed with the SEC a Rule 13e-3 Transaction Statement on Schedule 13E-3.

SPECIAL FACTORS

Purpose and Reasons for the Transaction

The purpose of the Transaction is to reduce the number of record holders of our common stock to fewer than 300, thereby enabling us to deregister our common stock under the Exchange Act and suspend our duty to file periodic reports and other information with the SEC thereunder. This will enable us to terminate Leafly’s status as a public reporting company with the SEC and reduce the financial costs and administrative burdens incurred with respect to such status.

Our Board believes that the costs of being a public reporting company currently outweigh the benefits of being a public reporting company and, thus, that it is no longer in the best interests of Leafly or its shareholders, creditors, or other stakeholders, including unaffiliated shareholders, for Leafly to remain a public reporting company.

The trading price of our common stock has significantly declined since February 4, 2022, when the Company consummated a business combination with Merida Merger Corp. I, Merida Merger Sub, Inc. (“Merger Sub I”), and Merida Merger Sub II, LLC (“Merger Sub II”), from a high of $231.60 during the quarter ended March 31, 2022 to a low of $0.13 on May 5, 2025. The current trading price of our common stock together with our significant debt levels would make using our common stock as a vehicle to raise capital or to provide acquisition consideration practically impossible.

In addition, the legal requirements of being a public reporting company create large administrative and financial costs for us. If we cease to be subject to the reporting requirements under the Exchange Act, we estimate that our savings will be between $1,800,000 and $2,000,000 per year, including, legal, accounting and printing and staff fees and costs attributable to complying with such reporting requirements. We believe that these financial resources and time devoted to ongoing reporting could more effectively be devoted to other purposes. The going private transaction will also allow our management and employees to devote more time and effort to improving our operations by eliminating the time spent complying with our financial reporting requirements under the Exchange Act and managing shareholder relations.

In light of these factors, our Board reasonably believes that Leafly should go private through the Reverse Stock Split. We believe that we will reduce our expenses since we will no longer need to incur those costs associated with compliance with the reporting requirements of a public company.

The Reverse Stock Split will also provide the shareholders with a very efficient way to cash out their investment because it is unlikely that their shares can be sold on the OTC Pink Open Market at the Cash-Out Price. The trading volume in our common stock has been, and continues to be, limited. The average daily trading volume of our common stock over the twelve-month, six-month and three-month periods ended March 31, 2025 was approximately 371,700, 40,300 and 36,200 shares, respectively. The 30-day, 60-day and 90-day volume-weighted average price of our common stock as of March 31, 2025 was $0.23, $0.57 and $0.90, respectively. In addition to the liquidity provided by the Transaction, shareholders with small holdings will avoid incurring brokerage fees that are disproportionately high relative to the market value of our common stock if they sold their shares in the market.

Previous Contacts and Negotiations

As described in detail below under “Transaction Information – Background of the Transaction”, since early 2024, the Board spent extensive time exploring various strategic alternatives for the Company. The Board considered strategic transactions, financing transactions, and insolvency proceedings. Notably, because the Company is involved in the cannabis industry, it has limited options with respect to bankruptcy relief. The Company engaged a financial advisor to engage in a process to market the Company, including outreach to potential interested third parties with respect to a merger; consolidation; acquisition; equity investment or sale or other transfer of a material amount of assets of the subject company. While the Company received several non-binding indications of interest and engaged in negotiations with several prospective strategic partners, the Company received no firm offers and was ultimately unable to negotiate a strategic transaction that the Board of Directors believed would be in the best interests of the Company’s stockholders. Any indications of interest were unlikely to result in any payments to shareholders with respect to their shares of common stock because the proposed purchase price was at or below the amount of the Company’s outstanding debt under the Notes. In addition, a third party made unsolicited non-binding acquisition proposals to the Company in early 2024 and early 2025, but such proposals were determined by the Board to be immaterial in terms of offered consideration and credibility, and was unlikely to lead to a bona fide offer resulting in consideration to the shareholders.

Other Alternatives to the Transaction

In addition to the marketing process described above with respect to a sale of the Company (as described in greater detail below under “TRANSACTION INFORMATION – Background of the Transaction”, our Board considered several alternatives in advance of authorizing the Transaction.

The Board considered a tender offer as a means of reducing the number of shareholders, but noted we would have had to hire a dealer manager and solicitation agent at relatively significant expense. Also, in a tender offer, there would have been no guarantee that enough shareholders would have tendered their shares to reduce the number of shareholders to below 300.

Our Board also considered having Leafly continue as a public company. However, given the costs savings that will be achieved from eliminating our status as a public company and the lack of any significant benefit that we derive out of being a public company, our Board believes that “going private” is in the best interests of Leafly.

The Board did not consider a forward stock split.

Effects of the Transaction

Effects of the Transaction on Leafly

After the Transaction is completed, the number of record shareholders of our common stock will be reduced to below 300, which will enable us to deregister our common stock under the Exchange Act and suspend our duty to file periodic reports and other information with the SEC thereunder, which will substantially reduce the information required to be furnished by us to the public, including our shareholders. We will cease to file annual, quarterly, current, and other reports and documents with the SEC, and shareholders will cease to receive annual reports and proxy statements.

We intend to apply for deregistration of our common stock and suspension of our duty to file periodic reports and other information as soon as practicable following completion of the Transaction. See “— Purpose and Reasons for the Transaction.” However, our Board reserves the right, in its discretion, to abandon, postpone or modify the Transaction prior to the effective date of the Reverse Stock Split if it determines that doing so is in our best interests and the best interests of our shareholders. See “— Reservation.”

Other than as described in this Proxy Statement, neither Leafly nor its management has any current plans or proposals to do any of the following: effect any extraordinary corporate transaction (such as a merger, reorganization or liquidation); sell or transfer any material amount of Leafly’s assets; change the composition of our Board or management; change materially our dividend rate or policy, indebtedness or capitalization; or otherwise effect any material change in Leafly’s corporate structure or business. However, we are continuing to explore raising capital to help pay down our debt and/or provide us with growth capital, and our secured debtholder could foreclose on our assets upon a default at the currently scheduled maturity date of July 1, 2025. We may also undergo one or more of the extraordinary types of transactions identified above in an effort to restructure that existing secured debt.

We may, at our option at various times in the future, use such methods as we deem appropriate to ensure that the number of record holders of our common stock remains less than 300 under applicable SEC rules. We cannot predict the likelihood, timing or means of events, if any.

Effects of the Transaction on Our Shareholders

When the Transaction is consummated, Discontinued Shareholders (those owning fewer than Ratio Number pre-Reverse Stock Split shares) will no longer have any equity interest and will not participate in our future earnings or any increases in the value of our assets or operations. Only our Continuing Shareholders will benefit from any future increase in our earnings. The Continuing Shareholders will continue to have an equity interest in Leafly after the Transaction and will own common stock, the liquidity of which may be severely restricted.

Once we terminate the registration of our common stock and suspend our duty to file periodic reports and other information with the SEC, any trading in our common stock after the Transaction and deregistration under the Exchange Act will only occur in privately negotiated sales and potentially on the OTC Pink Open Market, if one or more brokers chooses to make a market for our common stock there and complies with applicable regulatory requirements. We have been traded on the OTC Pink Open Markets since our delisting from Nasdaq became effective on January 17, 2025.

The OTC Pink Open Market is the lowest tier of the three marketplaces for trading of OTC securities, which is a broker platform for trading securities operated by the OTC Markets Group Inc. There are no financial standards or disclosure requirements. For more information about the OTC Markets Group, see https://www.otcmarkets.com/. To be traded on the OTC, a broker dealer would need to

submit a Form 211 with the Financial Industry Regulatory Authority (“FINRA”), and obtain FINRA approval for trading in the common stock. If such trading in our common stock were to develop on the OTC, we would expect it to occur at the Pink-No Information tier. The OTC Pink Open Market is not a stock exchange and we do not have the ability to list on, or control whether our shares are quoted on the OTC Pink Open Market. There is no assurance that there will be any OTC Pink Open Market quotations after the Transaction or that, if such quotations begin, they will continue for any length of time. Even if they do, the liquidity of our securities will be further limited because many brokers do not trade securities listed in the OTC Pink Open Market.

Furthermore, any remaining shareholders that hold “restricted securities” or “control securities”, within the meaning of Rule 144 of the Securities Act of 1933, as amended, may no longer be eligible to rely on Rule 144 to sell their shares. Rule 144 provides a safe harbor for the resale of restricted securities (i.e. sold in a private placement) or control securities under this Section 4(a)(1) exemption. It provides that if certain conditions are met (i.e. holding period, public information, etc.), a shareholder can sell restricted securities or control securities and not be deemed an “underwriter”. Securities of a former shell company, like Leafly, can be sold in reliance on Rule 144 if the issuer is subject to the reporting requirements of section 13 or 15(d) of the Exchange Act; has filed all reports and other materials required to be filed by section 13 or 15(d) of the Exchange Act, as applicable, during the preceding 12 months (or for such shorter period that the issuer was required to file such reports and materials), other than Form 8-K reports; and has filed current “Form 10 information” with the SEC reflecting the issue is no longer a shell company; and one year has elapsed from the date that the issuer filed “Form 10 information” with the Commission. If the Company is no longer subject to the reporting requirements of section 13 or 15(d), as will be the case after the Company files its Form 15, this safe harbor may not be available and holders of “restricted securities” or “control securities” will need to avail themselves of a different exemption in order to sell their shares. Note: If the shareholder wants to continue the investment in Leafly, before the effective date of the Reverse Stock Split, Shareholders holding restricted securities would be able to sell their securities pursuant to Rule 144 until the Company files its Form 15, so long as the Company has filed all reports and other materials required to be filed by section 13 or 15(d) of the Exchange Act, as applicable, during the preceding 12 months (or for such shorter period that the issuer was required to file such reports and materials), other than Form 8-K reports. As of the date of this filing, the Company has filed all such reports.

Discontinued Shareholders will, following the Transaction, have their pre-Reverse Stock Split shares cancelled and converted into the right to receive a cash payment. As soon as practicable after the effective date of the Reverse Stock Split, we will send these shareholders a letter of transmittal with instructions as to how such shareholders will be paid the cash payment. The letter of transmittal will include instructions on how to surrender stock certificates. Continuing Shareholders will not receive any cash payment for their whole shares.

If your shares are held in a stock brokerage account or by a bank or other nominee, you are considered the beneficial owner of shares held in “street name” with respect to those shares. Your broker or other nominee is considered, with respect to those shares, the shareholder of record. Although the Transaction is designed to reduce the number of shareholders of record, we intend to treat shareholders holding common stock in street name held through a broker or other nominee in the same manner as shareholders whose shares are registered in their names for purposes of the Transaction. Nominees will be instructed to effect the Transaction for their beneficial owners. However, nominees may have different administrative procedures with respect to how they communicate with beneficial owners, and shareholders owning shares in street name should contact their nominee(s).

Based on information available to us as of the date of this Proxy Statement, we estimate that the Transaction will reduce the number of record holders of our common stock from approximately 432 to approximately a range of 170 to 180. Leafly’s rationale for applying the Reverse Stock Split ratio in a range from 1 for 200 to 1 for 500 to all shareholders is that if a large enough number of holders holding in street name remained following the Transaction, and thereafter became shareholders of record, Leafly could again become subject to reporting obligations under Sections 15(d) or 12(g) of the Exchange Act. By reducing the number of shareholders of record well below 300 and reducing the number of holders holding in street name, we believe we have sufficiently limited the risk of having to re-commence filing reports with the SEC and to re-register under the Exchange Act.

Effects of the Transaction on Executive Officers, Directors and Greater than 5% Holders

For information regarding the voting ownership percentage before and after the Transaction of each of our named executive officers, our directors and persons that beneficially own greater than 5% of our common stock, see “Leafly Information — Security and Voting Ownership of Certain Beneficial Owners and Management.”

Pursuant to Section 16(a) of the Exchange Act, directors, executive officers, and 10% shareholders of companies who have shares registered under the Exchange Act are required to report changes in their respective beneficial ownership of such shares to the SEC. Such insiders are required to file an initial Form 3 showing their respective beneficial holdings within 10 days after becoming subject to Section 16(a). Thereafter, a reporting insider is generally required to file a report on Form 4 within two business days following most acquisitions and dispositions of company shares by the insider. As a related deterrent to improper trading on inside information, insiders are also subject to the so-called short-swing profit disgorgement requirements of Section 16(b) of the Exchange Act. In general, these requirements mandate the disgorgement by an insider of any paper profit realized on a purchase and a sale of company stock which

occur within a six-month period. Transactions are generally paired so as to match the lowest purchase price and the highest sale price within the six-month period, thus extracting the maximum “profit” from the insider on the transaction or transactions. If Leafly declines to press a claim for disgorgement, a claim for recovery of profit may be asserted by any shareholder on behalf of Leafly. In addition to the effects of the Transaction on shareholders generally, when we complete the Transaction and deregister our common stock, our insiders will no longer be required to comply with these requirements.

Pursuant to Section 13(d) of the Exchange Act, shareholders who beneficially own, directly or indirectly, more than 5% of our common stock are required to each file forms with the SEC containing information about such shareholder and the nature of the acquisition, and amendments thereto in certain circumstances. In addition to the effects of the Transaction on shareholders generally, when we complete the Transaction and deregister our common stock, shareholders who have acquired more than 5% of our common stock, and shareholders who may acquire more than 5% of our common stock in the future will no longer be required to comply with these requirements.

After the Form 15 is filed with the SEC, Leafly will no longer be subject to the periodic reporting requirements under the Exchange Act. Additionally, 90 days after the Form 15 is filed, Leafly’s common stock will be deregistered and Leafly will cease to be subject to the proxy rules under the Exchange Act, unless the SEC otherwise determines. As a result, information about our directors’ and officers’ compensation and share ownership will no longer be publicly available.

Potential Disadvantages of the Transaction to Shareholders

While we believe that the Transaction will result in the benefits described above, several disadvantages should also be noted:

Financial Effects of the Transaction

We estimate that completion of the Transaction will require us to spend approximately $190,000 in legal, financial and other fees and costs related to the Transaction. This estimate does not include the cost of the aggregate cash payment to for fractional shares, which we estimate will be approximately $125,000. These costs will be offset by the costs we would otherwise incur as a public reporting company to comply with SEC reporting requirements, which we estimate to be between $1,800,000 and $2,000,000 per year.

Fairness of the Transaction

Our Board has fully reviewed and considered the terms, purpose, alternatives and effects of the Transaction and has determined that the Transaction is in the best interests of Leafly and is substantively and procedurally fair to the unaffiliated shareholders of Leafly, including our unaffiliated Discontinued Shareholders who will be cashed-out as a result of the Transaction and our unaffiliated Continuing Shareholders who will continue to hold our common stock after the Transaction. After studying the Transaction and its anticipated effects on our shareholders, our Board unanimously approved the Transaction.

Substantive Fairness

In determining the fairness of the Transaction, our Board considered the factors discussed below, in addition to the alternative transactions discussed in “ — Alternatives to the Transaction.” In light of these factors, our Board believes that the Transaction is substantively fair to Leafly’s unaffiliated shareholders, including our unaffiliated Discontinued Shareholders who will be cashed-out as a result of the Transaction and our unaffiliated Continuing Shareholders who will continue to hold our common stock after the Transaction. Our Board did not assign specific weight to the factors set forth below in a formulaic fashion. Moreover, in their considerations, individual directors may have given differing weights to different factors. However, our Board did place special emphasis on the significant cost and time savings we expect Leafly to realize from deregistration of our common stock under the Exchange Act and the suspension of our duty to file periodic reports and other information with the SEC, which will benefit our Continuing Stockholders.

Significant Cost and Time Savings. By deregistering our common stock and suspending our duty to file periodic reports with the SEC, we estimate that we will realize recurring annual cost savings of between $1,800,000 and $2,000,000 per year, as well as savings from personnel expense relating to the time spent by our management to prepare and review our reports and certifications required to be filed with the SEC under the Exchange Act. The Continuing Shareholders will benefit from these expected future cost savings. In addition, our Board has determined that the costs of being a public company, currently and in the foreseeable future, will continue to outweigh the benefits of being a public company and, thus, it is no longer in the best interests of Leafly or its shareholders, creditors, or other stakeholders, including its unaffiliated Continuing Shareholders and unaffiliated Discontinued Shareholders, for Leafly to remain a public reporting company. See the “— Purpose and Reasons for the Transaction.”

Opportunity to Remain a Holder of, or to Liquidate, Common Stock. Another factor considered by our Board in determining the fairness of the Transaction to holders of our common stock is the opportunity Leafly’s shareholders have to remain shareholders or to liquidate their Company holdings. Current holders of fewer than the Ratio Number shares of common stock can either remain Company shareholders by acquiring additional shares so that they own at least the Ratio Number common stock immediately before the effective date of the Reverse Stock Split or be cashed out in the Reverse Stock Split. If a shareholder purchases additional common stock, then the shareholder may incur brokerage fees or commission. Holders of fewer than the Ratio Number common stock at the effective time of the Reverse Stock Split will have their fractional post-Reverse Stock Split shares purchased by Leafly at the Cash-Out Price, which as discussed below will determined based on the trading prices during the period leading up to the approval of the Transaction, if approved. Our Board did not quantify the consideration of brokerage fees and commissions paid for having such fractional shares cashed out in the Reverse Stock Split since such fees, if any, vary significantly depending upon the method used to acquire or dispose of shares. Conversely, shareholders who own the Ratio Number shares or more and who desire to liquidate their shares in connection with the Transaction at the premium price offered can reduce their holdings to less than the lowest Ratio Number of shares by selling or gifting shares prior to the effective date of the Reverse Stock Split. Our Board did not place undue emphasis on this factor due to the limited trading market for our common stock. See “— Purpose and Reasons for the Transaction” and “— Structure of the Transaction.”

Recent and Historical Trading Prices. Our Board considered recent and historical trades of our common stock. The recent and historical trading of our common stock relates to the fairness of the Transaction to unaffiliated shareholders because it provides some insight into how the market has historically valued our common stock. Since unaffiliated Discontinued Shareholders will no longer be able to directly participate in the financial success of Leafly, the Cash-Out Price paid to these shareholders as a result of the Reverse Stock Split represents the final opportunity to obtain value for their investment. Although not a perfect measure, the trends over time in the market price of our common stock reflect market perceptions about Leafly’s intrinsic value.

In its deliberations concerning the fairness of the Transaction, our Board considered:

The Cash-Out Price of $0.28 per share represents approximately a 56% premium over the closing sales price of our common stock on the initial Record Date of April 2, 2025, and the date prior to the filing of the initial preliminary proxy statement, approximately a 40% premium over 10-Day VWAP and approximately a 22% premium over the 30-Day VWAP. Our Board believes that the April 2, 2025 closing price of our common stock, the closing price of the day prior to the filing of the initial preliminary proxy statement announcing the intention to engage in the Transaction, the 10-Day VWAP and the 30-Day VWAP are relevant data points because they reflect the most recent market data. Our Board believes that using these data points supports the Board’s fairness determination, in light of the relatively illiquid market for the common stock and the resulting inability to sell common stock in any quantity without exerting downward pressure on the trading price of the common stock. In addition, our Board believes the 30-Day VWAP is a relevant data point, as it demonstrates that the common stock has traded at these low levels for an extended period of time, especially after the Company’s securities were delisted from Nasdaq. The Board believes that trading prices from prior to the delisting of the common stock from Nasdaq, is less relevant because that trading price does not reflect the significantly reduced liquidity available for the common stock on the OTC Pink Open Market, as evidenced by the steep decline in the trading price of the common stock upon delisting. Accordingly, our Board believes that the recent and historical trading prices support the Board’s determination that Cash-Out Price is fair to the unaffiliated Discontinued Stockholders and the unaffiliated Continuing Stockholders.

Notably, the Cash-Out Price of $0.28 per share continues to be a significant premium to trading prices after the Board’s determination of the Cash-Out Price. Since April 10, 2025, the Company’s common stock has traded in a range from a high of $0.31 to a low of $0.13. The Cash-Out Price represents an 17% premium over the closing sales price of $0.24 on May 8, 2025, the last day trading day prior to filing our definitive proxy statement.

Net Book Value of Our Common Stock, Excluding Non-Controlling Interest and Intangible Assets. Our net book value per outstanding common share as of December 31, 2024 and September 30, 2024 was negative $4.91 and negative $4.81, respectively. In considering the fairness of the Cash-Out Price, the Board considered that the net book value per share of common stock is negative supported the concept that the fair value of the common stock likely did not exceed the recent trading prices. Given that the Cash-Out Price will be positive while the net book value of our common stock is negative, the Cash-Out Price of $0.28 is a premium of $5.19 to the net book value per share as of December 31, 2024.

Other Considerations of Value. In considering the fairness of the Cash-Out Price, the Board also considered the Company’s going concern status, as discussed in greater detail below under “Leafly – Going Concern Status” on page 42.

Treatment of Affiliated and Unaffiliated Holders of Our Common Stock. The Transaction will not affect holders of our common stock differently on the basis of affiliate status. The sole determining factor in whether a shareholder will be cashed out or will continue as a holder of our common stock as a result of the Transaction is the number of common stock held by the shareholder as of the effective date of the Reverse Stock Split. However, all of our Board, including Alan Pickerill who was a Board member at the time the Reverse Stock Split was approved by the Board, and all of our executive officers hold in excess of the highest possible Ratio Number shares. Accordingly, they will not be cashed out in the Transaction, but will receive cash for any fractional shares on the same terms as any other stockholder. The range of Reverse Stock Split ratios was selected solely based on the need to have fewer than 300 record holders after the Transaction in order to deregister and suspend our reporting obligations under the Exchange Act. While none of our affiliates that hold common stock will be cashed out in the Transaction, affiliates and non-affiliates will be treated equally in the Transaction, with any non-affiliate holding at least the Ratio Number of shares of common stock continuing to be a shareholder of Leafly.

Minimum Effect on Voting Power. The Transaction will have a minimum effect on the voting power of Leafly’s shareholders. The voting and other rights of our common stock will not be affected by the Transaction. The only effect of the Transaction on Leafly’s voting power will be a slight change in the overall ownership percentage of the Continuing Shareholders following the Transaction.

Minimum Effect on Shareholder Rights. The Transaction will not materially change the rights, preferences or limitations of the Continuing Shareholders.

Immediate Cash Payment. Those shareholders who own less than the Ratio Number of shares of our pre-Reverse Stock Split shares will receive an immediate cash payment of the Cash-Out Price per pre-Reverse Stock Split common share and will not pay any brokerage fees, commissions or transaction costs that such shareholders would have to pay if they were to sell their shares in the open market.

Potential Disadvantages of the Transaction. When considering the fairness of the Transaction, our Board also considered the following possible disadvantages of effecting the Transaction:

Possible Decline in Liquidity and Price of Our Common Stock. After the completion of the Transaction, our Continuing Shareholders may experience reduced liquidity for our common stock. This reduced liquidity may adversely affect the market price of our common stock. See “— Effects of the Transaction — Potential Disadvantages of the Transaction to Shareholders” and “— Significantly Reduced Public Disclosure of Information About Leafly” immediately below.

Significantly Reduced Public Disclosure of Information About Leafly. After deregistration of our common stock and suspension of our duty to file periodic reports and other information with the SEC, information regarding our operations and financial results that are currently available to the general public and our shareholders will no longer be readily available. However, we expect our common stock to continue to trade in the OTC Pink Open Market (a centralized quotation service that collects and publishes market maker quotes for securities). The amount of information required to be disclosed to facilitate trading in the OTC Pink marketplace is significantly less than the amount of information Leafly currently publicly discloses as a company with a class of securities registered under the Exchange Act. In addition, in the future, we may no longer trade in the OTC Pink Open Market. In which case, shareholders will have to make a request of Leafly if they want to be provided with information that Leafly is not otherwise required to provide by law. We may or may not provide shareholders with information, upon request or otherwise, that we are not required by law to provide. Our Board believes that the overall benefits to Leafly of no longer being a public reporting company substantially outweigh the disadvantages associated with decreased publicly available information about Leafly. See “— Effects of the Transaction — Potential Disadvantages of the Transaction to Shareholders.”

Sarbanes-Oxley Act and Other Reporting and Disclosure Provisions Will No Longer Apply to Leafly. After the completion of the Transaction and the deregistration of our common stock and suspension of our duty to file periodic reports and other information with the SEC, we will no longer be subject to the provisions of the Sarbanes-Oxley Act or the liability provisions of the Exchange Act that apply to public companies, including the requirement that the chief executive officer and the chief financial officer certify the accuracy of the financial statements contained in our periodic reports. In addition, our officers, board members? and 10% or greater shareholders will no longer be subject to the short-swing profit disgorgement provisions and reporting requirements of Section 16 of the Exchange Act. See “— Effects of the Transaction — Potential Disadvantages of the Transaction to Shareholders.”

Leafly Will No Longer Have the Potential Benefits Normally Associated with Public Reporting Company Status. Another potential disadvantage of the Transaction is that we will no longer have the benefits associated with being a public reporting company, such as better access to the capital markets for issuances of securities. We would still have access to capital markets, but if we were to conduct a public offering of our securities, we would have to again become a reporting company, which would be a lengthy and expensive process, and the expenses that we are seeking to eliminate would then be reinstated. We believe that the cost savings from ceasing to be a public reporting company outweigh the drawbacks of losing more ready access to the capital markets.

Holders of Restricted Stock or Control Securities Will Have a More Difficult Time Selling Their Shares. Furthermore, any remaining shareholders that holder “restricted securities” or “control securities”, within the meaning of Rule 144 of the Securities Act of 1933, as amended. Rule 144 provides a safe harbor for the resale of restricted securities (i.e. sold in a private placement) or control securities under this Section 4(a)(1) exemption. It provides that if certain conditions are met (i.e. holding period, public information, etc.), a shareholder can sell restricted securities or control securities and not be deemed an “underwriter”. Securities of a former shell company, like Leafly, can be sold in reliance on Rule 144 if the issuer is subject to the reporting requirements of section 13 or 15(d) of the Exchange Act; has filed all reports and other materials required to be filed by section 13 or 15(d) of the Exchange Act, as applicable, during the preceding 12 months (or for such shorter period that the issuer was required to file such reports and materials), other than Form 8-K reports; and has filed current “Form 10 information” with the SEC reflecting the issue is no longer a shell company; and one year has elapsed from the date that the issuer filed “Form 10 information” with the Commission. If the Company is no longer subject to the reporting requirements of section 13 or 15(d), as will be the case after the Company files its Form 15, this safe harbor may not be available and holders of “restricted securities” or “control securities” will need to avail themselves of a different exemption in order to sell their shares. Shareholders holding restricted securities would be able to sell their securities pursuant to Rule 144 until the Company files its Form 15, so long as the Company has filed all reports and other materials required to be filed by section 13 or 15(d) of the Exchange Act, as applicable, during the preceding 12 months (or for such shorter period that the issuer was

required to file such reports and materials), other than Form 8-K reports. As of the date of this filing, the Company has filed all such reports.

Discontinued Shareholders Will Not Participate in Any Future Increases in Our Value. Following the Transaction, Discontinued Shareholders will no longer have an equity interest in Leafly and will not participate in our future earnings or any increases in the value of our assets or operations. See “— Effects of the Transaction — Potential Disadvantages of the Transaction to Shareholders.”

Going Concern Valuation. An indicator of going concern value is the discounted future cash receipts approach. Given the other considerations discussed herein, our Board did not pursue this approach due to the significance of the subjective assumptions that would be involved in such an approach, as well as the expense associated with the approach.

Liquidation Value. Our Board viewed the liquidation value of Leafly to be an inappropriate measure for the purpose of evaluating the fairness of the Cash-Out Price. Given that the Company’s assets are primarily intellectual property, software and know-how, the Board determined that the value of the business is better reflected based on continuing operations, and not from a liquidation perspective. A liquidation process would also involve additional legal fees, costs of sale and other expenses that would reduce any amounts that stockholders might receive upon a liquidation. Given the other factors considered by our Board as described in this Proxy Statement, our Board did not pursue a liquidation value approach.

Purchase Price Paid for Repurchases of Our Common Stock. We have not repurchased any of our common stock in the last two years. Accordingly, our Board could not consider repurchase prices in determining the fairness of the Transaction.

Our Board believes that all of the factors mentioned above, both favorable and unfavorable, when viewed together support a conclusion that the Transaction is substantively fair to all of Leafly shareholders, including the unaffiliated Discontinued Shareholders who will be cashed out as a result of the Transaction and the unaffiliated Continuing Shareholders who will continue to be shareholders of Leafly after the Transaction.

Procedural Fairness of the Transaction

In addition to the fairness of the substance of the Transaction, our Board believes that the process by which decisions were made regarding the Transaction is fair to Leafly’s affiliated and the unaffiliated shareholders, including the unaffiliated Discontinued Shareholders who will be cashed out as a result of the Transaction and the unaffiliated Continuing Shareholders who will continue to be shareholders of Leafly after the Transaction.

Our Board, which at the time the Transaction was considered and approved consisted of at least 50% of directors that were independent under the independence standards of Nasdaq and our Chief Executive Officer and President, unanimously approved the Transaction. Given the independence of the directors approving the Transaction and the lack of conflicts of interest with respect of our management and the Transaction, our Board did not consider it necessary to appoint a special committee to negotiate and approve the Transaction.

Our Board has not granted unaffiliated shareholders access to our corporate files nor has it extended the right to retain counsel or appraisal services at our expense. With respect to unaffiliated shareholders’ access to our corporate files, our Board believes that this Proxy Statement, together with our other filings with the SEC, provide adequate information for unaffiliated shareholders.

Shareholder Vote. The Transaction will require approval of holders of a majority of the outstanding voting power of the Company entitled to vote thereon, which in this case will mean the common stock and the Series A Preferred Stock voting together as a single class. The Series A Preferred Stock (“Series A Preferred Stock” or “Series A Preferred”) was issued to address the increasing challenge faced by many corporations in obtaining stockholder approval by a majority of outstanding shares for a modifications to a certificate of incorporation like the Amendment, given that many outstanding shares of public companies are held by brokers and other record holders in “street name” and was issued solely for purposes of assisting the Company in obtaining the majority of outstanding vote requirement needed to approve the Amendment. The Series A Preferred Stock, as described in greater detail below, will have 100,000,000 votes with respect to the Transaction, but can only exercise those votes in a manner that mirrors the votes cast by holders of common stock on the Transaction.

The directors and officers of the Company only hold approximately 6.9% of the voting power of the common stock as of the Record Date, which would not represent a majority even if the number of votes cast were limited to the minimum number of votes needed to reach a quorum. While Ms. Miyashita, as the sole holder of the Series A Preferred Stock, has additional voting power, because of the restrictions on the Series A Preferred Stock, the Series A Preferred Stock cannot be used to approve the Transaction if it is not otherwise approved by a majority of the votes cast by the common stock.

Although potentially relevant to a determination of fairness of the Transaction, the factors listed below, for the reasons given, were determined by our Board to not be applicable to Leafly and were not considered or were not given any weight by our Board.

Independent Representative

The independent members of our Board did not retain an unaffiliated representative to act solely on behalf of the unaffiliated shareholders for the purpose of setting the terms of the Transaction. In addition, our Board recognized the importance of preserving our cash position and completing the Transaction as expeditiously as practicable.

Approval of Directors

The Transaction was approved by the Company’s Board of Directors, including the Company’s current two independent directors, Jeffrey Monat and Andres Nannetti. The Reverse Stock Split and range of Reverse Stock Split Ratios was also approved by a third independent director, Alan Pickerill, before his resignation on April 1, 2025. The Board of Directors, including Alan Pickerill also approved the submission of the Reverse Stock Split to the Company’s stockholders, with the recommendation that such proposal be approved.

Other Offers

During the past two years, we have not received any firm offers for a merger or consolidation with or into another company, or the sale or other transfer of all or substantially all of our assets, or a purchase of our securities by a person that would involve a change in our control. The Company’s efforts with respect to a potential strategic transaction are discussed above under “Previous Contacts and Negotiations.” Accordingly, our Board did not consider firm offers in making its determination with respect to the fairness of the Transaction. To the extent that the Company has received any indications of interest, the Board considered these, like considerations of net book value, as support for using a market based method for determining value, since the transactions proposed by the indications of interest would provide stockholders with less consideration than Cash-Out Price as proposed; all non-binding indications of interest received suggested an enterprise value for the Company that was less than the amount of the outstanding Notes.

Reports, Opinions, or Appraisals

Our Board did not receive a report, opinion or appraisal from an outside party as to the value of our common stock or the fairness of the Transaction to unaffiliated Discontinued Shareholders who will be cashed out as a result of the Transaction or unaffiliated Continuing Shareholders who will remain shareholders following the Transaction. Our Board concluded that there were already sufficient procedural safeguards without the expense of retaining an independent fairness advisor, particularly since a shareholder could change his or her stock holdings prior to the effective date of the Transaction in order to be cashed out as a result of the Transaction or continue as a shareholder of Leafly following the Transaction. In addition, our Board recognized the importance of preserving Leafly’s cash position and completing the Transaction as expeditiously as practicable.

LEAFLY HOLDINGS, INC.

600 1st Ave, Suite 330, PMB 88154

Seattle, WA 98104-2205

PROXY STATEMENT

FOR THE 2025 ANNUAL MEETING OF STOCKHOLDERS TO BE HELD ON July 25, 2024

INFORMATION ABOUT THE ANNUAL MEETING

Purpose, Date, and Time

This proxy statement (the “Proxy Statement”) is provided in connection with the solicitation of proxies by and on behalf of the board of directors (the “Board”) of Leafly Holdings, Inc. (“Leafly,” the “Company,” “we,” “us,” or “our”) for use at the 2025 annual meeting of stockholders to be held virtually on Wednesday, June 11, 2025, at 9:00 a.m. Pacific Time at the following virtual meeting link http://www.virtualshareholdermeeting.com/LFLY2025 and any adjournments or postponements thereof (the “Annual Meeting”). The mailing address of our principal executive offices is 600 1st Ave, Suite 330, PMB 88154, Seattle, WA 98104-2205. This Proxy Statement will be mailed on or about May 12, 2025 to holders of record of our common stock, par value $0.0001 per share (“common stock”), as of the close of business on May 9, 2025 (the “Record Date”).

Record Date; Outstanding Shares; Shares Entitled to Vote

The Board has fixed the close of business on May 9, 2025 as the record date (the “Record Date”) for determining the stockholders entitled to notice of, and to vote at, the Annual Meeting. On the Record Date, there were 3,137,382 shares of common stock outstanding and entitled to vote and one share of Series A Preferred Stock entitled to vote, but the Series A Preferred Stock is only entitled to vote on Proposal No. 3 (Approval of Amendment/Transaction).

Holders of record of common stock on the Record Date will be entitled to one vote per share on any matter that may properly come before the Annual Meeting and any adjournments or postponements of the Annual Meeting. As discussed in greater detail below, the holders of record of each share of Series A Preferred Stock will be entitled to 100,000,000 votes per share, but only on Proposal No. 3 (Approval of Amendment/Transaction) and such votes must mirror the votes cast by the common stock

A list of the names of stockholders entitled to vote at the Annual Meeting will be available for examination by any stockholder for any purpose germane to the Annual Meeting during ordinary business hours at the Company's corporate headquarters for the ten days preceding the Annual Meeting.

Stockholders of Record; Beneficial Owners

Stockholder of Record: Shares Registered in Your Name. If, at the close of business on the Record Date, your shares were registered directly in your name with Continental Stock Transfer & Trust Company, our transfer agent, then you are considered the stockholder of record with respect to those shares. As the stockholder of record, you have the right to grant your voting proxy directly to the individuals listed on the proxy card or to vote on your own behalf at the Annual Meeting.

Beneficial Owners: Shares Registered in the Name of a Broker, Bank or Other Nominee. If, at the close of business on the Record Date, your shares were held in a stock brokerage account or by a bank or other nominee on your behalf, then you are considered the beneficial owner of shares held in “street name.” As the beneficial owner, you have the right to direct your broker, bank or other nominee how to vote your shares by following the voting instructions your broker, bank or other nominee provides. If you do not provide your broker, bank or other nominee with instructions on how to vote your shares, your broker, bank or other nominee may, in its discretion, vote your shares with respect to routine matters but may not vote your shares with respect to any non-routine matters. Proposals 2 (Approval of Name Change) are deemed routine matters; Proposals 1 (Election of Directors), Proposal 3 (Approval of Amendment/Transaction) and Proposal 4 (Adjournment of Meeting) are deemed non-routine matters.

Virtual Stockholder Meeting

We will hold our Annual Meeting in a virtual only format, which will be conducted via a live webcast. Stockholders will have an equal opportunity to participate in the Annual Meeting online regardless of their geographic location. We designed the format of our Annual Meeting to ensure that our stockholders who participate in the Annual Meeting will be afforded the same rights and opportunities to participate as they would at an in-person meeting and to enhance stockholder access, participation and communication through online tools. Our directors will also participate in the virtual Annual Meeting.

Virtual Nature of the Annual Meeting

The Annual Meeting will be held “virtually” through a live audio webcast on Wednesday, June 11, 2025, at 9:00 a.m. Pacific Time. The meeting will only be conducted via an audio webcast. There will not be a physical meeting location and you will not be able to attend the Annual Meeting in person.

Access to the Audio Webcast of the Annual Meeting

The live audio webcast of the Annual Meeting will begin promptly at 9:00 a.m. Pacific Time. Online access to the audio webcast will open approximately fifteen minutes prior to the start of the Annual Meeting to allow time for you to log in and test the computer audio system. We encourage our stockholders to access the meeting prior to its start time. A replay of the webcast will be made publicly available 24 hours after the Annual Meeting at http://www.virtualshareholdermeeting.com/LFLY2025.

Log in Instructions

To participate in the virtual Annual Meeting, log in at http://www.virtualshareholdermeeting.com/LFLY2025. Stockholders will need their unique 16-digit control number which appears on the Notice, the proxy card or the voting instructions that accompanied the proxy materials. If you do not have a control number, please contact your broker, bank, or other nominee as soon as possible, so that you can be provided with a control number and gain access to the Annual Meeting.

Submitting questions at the virtual Annual Meeting

As part of the Annual Meeting, we will hold a live Q&A session, during which we intend to answer all questions submitted during the Annual Meeting that are pertinent to the Company and the meeting matters, as time permits. If you wish to submit a question during the Annual Meeting, visit http://www.virtualshareholdermeeting.com/LFLY2025, type your question into the “Ask a Question” field, and click “Submit.” Answers to any such questions that are not addressed during the Annual Meeting will be published following the meeting on the Company’s website at https://investor.leafly.com/ under the link “Governance.” Questions and answers will be grouped by topic and substantially similar questions will be grouped and answered once.

Technical Assistance

Beginning fifteen minutes prior to the start of and during the virtual Annual Meeting, we will have a support team ready to assist stockholders with any technical difficulties they may have accessing or hearing the virtual meeting.

If you encounter any difficulties accessing the virtual Annual Meeting during the check-in or meeting time, please call the technical support number that will be posted on the virtual stockholder meeting log-in page.

Voting shares prior to and at the virtual Annual Meeting

Stockholders may vote their shares at www.proxyvote.com, by telephone or by mail, prior to the virtual Annual Meeting or at http://www.virtualshareholdermeeting.com/LFLY2025 during the virtual Annual Meeting.

Proposals to be voted on at the Annual Meeting

Leafly stockholders are being asked to vote on the following proposals at the Annual Meeting:

Recommendation of the Board of Leafly

The Board unanimously recommends that Leafly’s stockholders vote “FOR” the nominee with respect to Proposal No. 1 and “FOR” Proposal Nos. 2, 3 and 4.

Quorum and Vote Required

The presence, in person or by duly executed proxy, of stockholders representing a 33 1∕3% of the voting power of all outstanding shares of common stock entitled to vote at the Annual Meeting will constitute a quorum. Shares are considered present “in person” if the holder of those shares attends the meeting using their unique 16-digit control number or by proxy if the holder properly voted by proxy in advance of the meeting. If a quorum is not present at the Annual Meeting, we expect that the Annual Meeting will be adjourned or postponed to solicit additional proxies.

With respect to Proposal No. 1 (Election of Director), the director must be elected by the affirmative vote of a plurality of the votes cast with respect to the director nominee by the stockholders present in person or represented by proxy at the Annual Meeting and entitled to vote for the election of directors, provided a quorum is present. With respect to Proposal No. 1, you may vote “FOR” or “WITHHOLD” authority to vote for each director nominee. If you “WITHHOLD” authority to vote with respect to the director nominee, your vote will have no effect on the election of the director nominee. Broker non-votes will have no effect on the election of the director nominee.

Approval of Proposal No. 2 (Approval of Name Change) will require the affirmative vote of a majority of the votes cast by the stockholders present in person or represented by proxy at the Annual Meeting and entitled to vote on the matter at the Annual Meeting, provided a quorum is present. While generally amendments to the Certificate of Incorporation requires approval of a majority of the outstanding voting power of the Company entitled to vote thereon, as discussed in Proposal No. 3 below, DGCL Section 242 does not require shareholder approval for changes to the corporate name. Therefore, Proposal No. 2 is an advisory vote that will only require a majority of the votes cast. A majority of the votes cast means that the number of votes cast “FOR” a proposal exceeds the number of votes cast “AGAINST” that proposal. With respect to Proposal No. 2, you may vote “FOR,” “AGAINST” or “ABSTAIN” from voting on each proposal. If you “ABSTAIN” from voting with respect to a proposal, your vote will have no effect on such proposal. As described below, we do not expect there to be broker non-votes with respect to Proposal No. 2.

Approval of Proposal No. 3 (Approval of Amendment/Transaction) will require approval of holders of a majority of the outstanding voting power of the Company entitled to vote thereon, which in this case will mean the common stock and the Series A Preferred Stock voting together as a single class. Ms. Miyashita will cast the 100,000,000 votes represented by the share of Series A Preferred on Proposal No. 3 in a manner that mirrors the votes cast by holders of common stock on such proposal. Without the issuance of the share of Series A Preferred Stock, abstentions and any other non-votes would have had the same effect as a vote against Proposal No. 3. Following the issuance of the share of Series A Preferred Stock, abstentions and any other non-votes on Proposal No. 3 will still technically have the same effect as a vote against such proposal, but because the share of Series A Preferred has a high number of votes and will vote in a manner that mirrors votes actually cast by the holders of common stock (which does not include abstentions or any other non-votes), abstentions and any other non-votes will have no effect on the manner in which the Series A Preferred Stock votes are cast. The Series A Preferred Stock (“Series A Preferred Stock” or “Series A Preferred”) was issued to address the increasing challenge faced by many corporations in obtaining stockholder approval by a majority of outstanding shares for a modifications to a certificate of incorporation like the Amendment, given that many outstanding shares of public companies are held by brokers and other record holders in “street name” and was issued solely for purposes of assisting the Company in obtaining the majority of outstanding vote requirement needed to approve the Amendment. See “Special Factors — Fairness of the Transaction” and “Other Matters Related to the Transaction — Stockholder Approval of the Transaction” beginning on pages xi and 37, respectively.

Approval of Proposal No. 4 (Approval of One or More Adjournments to the Annual Meeting) will require the affirmative vote of a majority of the votes cast by the stockholders present in person or represented by proxy at the Annual Meeting and entitled to vote on the matter at the Annual Meeting, provided, that in the absence of a quorum, the affirmative vote of the holders of a majority of the shares represented thereat is required for the approval of this Proposal No. 4. A majority of the votes cast means that the number of votes cast “FOR” a proposal exceeds the number of votes cast “AGAINST” that proposal. With respect to Proposal No. 4, you may vote “FOR,” “AGAINST” or “ABSTAIN” from voting on each proposal. If you “ABSTAIN” from voting with respect to a proposal, your vote will have no effect on such proposal. Broker non-votes will have no effect on the approval of Proposal No. 4. However, this proposal is being submitted on an advisory basis. Regardless of whether this proposal is approved, pursuant to our Bylaws, the chairman of the meeting may also authorize the adjournment of the Annual Meeting in his discretion, to the extent permitted by applicable law.

Voting; Proxies; Revocation

Shares of our Common Stock represented at the Annual Meeting by properly executed proxies received prior to the Annual Meeting, and not revoked prior to or at the Annual Meeting, will be voted at the Annual Meeting, and at any adjournments, continuations or postponements of the Annual Meeting, in accordance with the instructions on the proxies.

Stockholder of Record: Shares Registered in Your Name. If you are a stockholder of record, you can vote in one of the following ways:

Beneficial Owners: Shares Registered in the Name of a Broker, Bank or Other Nominee. If you are the beneficial owner of shares held of record by a broker, bank or other nominee, you will receive voting instructions from your broker, bank or other nominee. You must follow the voting instructions provided by your broker, bank or other nominee in order to instruct your broker, bank or other nominee how to vote your shares. The availability of Internet and telephone voting options will depend on the voting process of your broker, bank or other nominee.

Stockholder of Record: Shares Registered in Your Name. If you are a stockholder of record and you submit a duly executed proxy, but you do not provide voting instructions, your shares will be voted:

Beneficial Owners: Shares Registered in the Name of a Broker, Bank or Other Nominee. If you are a beneficial owner and you do not provide your broker, bank or other nominee that holds your shares with voting instructions, then your broker, bank or other nominee will determine if it has discretion to vote on each matter. Brokers do not have discretion to vote on non-routine matters. Proposal No. 1 (Election of Directors), 3 (Approval of Amendment/Transaction) and 4 (Approval of One or More Adjournments to the Annual Meeting) are non-routine matters, while Proposal No. 2 (Approval of Name Change), is a routine matter. As a result, if you do not provide voting instructions to your broker, bank or other nominee, then your broker, bank or other nominee may not vote your shares with respect to Proposals No. 1, 3 and 4, which would result in a “broker non-vote,” but may, in its discretion, vote your shares with respect to Proposal No. 2.

A record holder who executes a proxy may revoke it before or at the Annual Meeting by: (i) entering a new vote by Internet or telephone; (ii) attending the Annual Meeting and voting at that time; (iii) duly executing, dating and delivering a new proxy card with a later date; or (iv) delivering to our Secretary a written notice of revocation of a previously delivered proxy, with such notice dated after the previously delivered proxy. Attending the Annual Meeting will not, in and of itself, constitute revocation of a proxy. Any written notice revoking a proxy should be delivered to Leafly Holdings, Inc., 600 1st Ave, Suite 330, PMB 88154 Seattle, WA 98104 Attention: Kathleen Mullaney, Assistant Secretary or via email to kathleen.mullaney@leafly.com. If your shares of Common Stock are held in a brokerage account, you must follow your broker’s instructions to revoke a proxy.

Abstentions and Broker Non-Votes

Broker non-votes occur when a nominee holding shares of voting securities for a beneficial owner does not vote on a particular proposal because the nominee does not have discretionary voting power on that item and has not received instructions from the beneficial owner. Abstentions, withheld votes, and broker non-votes are included in determining whether a quorum is present but are not deemed a vote cast “FOR” or “AGAINST” a given proposal. As such, abstentions, withheld votes and broker non-votes do not affect the voting results with respect to Proposal No. 1 (Election of Directors), Proposal No. 2 (Approval of
Name Change), or Proposal No. 4 (Approval of One or More Adjournments to the Annual Meeting), or any other items requiring the affirmative vote of a majority of the votes cast by the stockholders present in person or represented by proxy at the Annual Meeting and entitled to vote thereon. As discussed above, abstentions and broker non-votes will have a limited impact on the voting results with respect to Proposal No. 3 (Approval of Amendment/Transaction) because of the impact of the Series A Preferred Stock.

Proxy Solicitation Costs

We are soliciting proxies for the Annual Meeting from our stockholders. We will bear the expense of soliciting proxies and have hired Sodali & Co., 333 Ludlow Street, 5th Floor, South Tower, Stamford, CT 06902, to assist in the proxy solicitation process. We will pay Sodali & Co. a fee of $10,000, plus expenses. Copies of solicitation materials will be furnished to brokerage houses, fiduciaries and custodians holding Common Stock for the benefit of others so that such brokerage houses, fiduciaries and custodians may forward the solicitation materials to such beneficial owners. We may reimburse persons representing beneficial owners of common stock for their expenses in forwarding solicitation materials to those beneficial owners. Original solicitation of proxies by mail may be supplemented by telephone or personal solicitation by our directors, officers or other regular employees of the Company. No additional compensation will be paid to our directors, officers or other regular employees for these services.

Business; Adjournments

We do not expect that any matter other than the proposals presented in this Proxy Statement will be brought before the Annual Meeting. However, if other matters are properly presented at the Annual Meeting or in the event of any adjournments or postponements of the Annual Meeting, then the proxy holders will vote in their discretion with respect to those matters.

The Annual Meeting may be adjourned by the Chairman of the Board, to the extent permitted by applicable law and our governing documents, or by the affirmative vote of a majority of the shares of our common stock cast by the stockholders present in person or represented by proxy at the Annual Meeting and entitled to vote at the Annual Meeting. In the case that a quorum is not present at the Annual Meeting, or in the case that a quorum is present at the Annual Meeting but there are not sufficient votes at the time of the Annual Meeting to adopt Proposal No. 3 (Approval of Amendment/Transaction), then the chairman of the Special Meeting has the power to adjourn the Special Meeting, or, alternatively, stockholders may be asked to vote, on an advisory basis, on a proposal to adjourn the Annual Meeting in order to permit the further solicitation of proxies.

Inspector of Elections

Broadridge Financial Solutions, Inc. (“Broadridge”) tabulates the votes at the Annual Meeting, and a Representative of Broadridge will serve as the independent inspector of election.

Receipt of More Than One Set of Voting Materials

Stockholders may receive more than one set of voting materials, including multiple copies of this Proxy Statement and multiple proxy cards or voting instruction cards. For example, if you hold your shares in more than one brokerage account, you will receive a separate voting instruction card for each brokerage account in which you hold shares. If you are a holder of record and your shares are registered under more than one name, you will receive more than one proxy card. Please complete, sign, date and return each proxy card and voting instruction card that you receive in order to cast a vote with respect to all of your shares.

Householding of Proxy Materials

We have adopted a procedure approved by the SEC called “householding.” Under this procedure, we will mail one set of proxy materials, one copy of our Annual Report and this Proxy Statement, to multiple stockholders who share the same address (if they appear to be members of the same family) unless we have received contrary instructions from an affected stockholder. Stockholders who participate in householding will continue to receive separate proxy cards. This procedure reduces our printing and mailing costs. Upon written or oral request, we will promptly deliver a separate copy of the proxy materials and Annual Report to any stockholder at a shared address to which we delivered a single copy of any of these documents. To receive a separate copy, or, if you are receiving multiple copies, to request that we only send a single copy of next year’s proxy materials and annual report, you may contact us as follows:

Leafly Holdings, Inc.

Attention: Kathleen Mullaney
Assistant Secretary
600 1st Ave, Suite 330, PMB 88154

Seattle, WA 98104-2205
Email: kathleen.mullaney@leafly.com

Stockholders who hold shares in street name may contact their brokerage firm, bank, broker-dealer or other nominee to request information about householding.

Reporting of Voting Results

Preliminary voting results will be announced at the Annual Meeting. In addition, final voting results will be published in a Current Report on Form 8-K that will be filed within four business days of the Annual Meeting. If final voting results are not available to us at that time, we will file a Form 8-K to publish preliminary results and, within four business days after the final results are known to us, file an amendment to the Form 8-K to publish the final results.

reduction to the number of shares of authorized common stock from 200,000,000,000 to 5,000,000 and authorized preferred stock from 5,000,000 to 1,000,000 (the “Authorized Share Reduction”).

If approved by our stockholders at the Annual Meeting, at the discretion of the Board of Directors and as further described below, we would affect the Reverse Stock Split and the Authorized Share Reduction by causing the filing of the Amendment, a copy of which is attached as Annex A to this Proxy Statement, with the Delaware Secretary of State.

As described below, the Board of Directors, in its discretion, may also determine not to effect the Reverse Stock Split and the Authorized Share Reduction. We will not affect the Reverse Stock Split without also effecting the Authorized Share Reduction, and vice versa. While we intend to effect the Amendment as soon as possible after the Annual Meeting, if the Board of Directors, in its discretion, determines not to effect the Amendment prior to the one-year anniversary of the date of this Annual Meeting (the “Anniversary Date”), the Amendment will be abandoned. If our stockholders approve the Amendment at this Annual Meeting, no further action on the part of stockholders will be required to either implement or abandon the Amendment.

If approved by our stockholders, this Proposal No. 3 (Approve of Amendment/Transaction) would permit, but would not require, the Board of Directors to effect a Reverse Stock Split of our common stock issued and outstanding or held in treasury by a ratio between 1 for 200 and 1 for 500, with the final ratio to be set in the discretion of the Board of Directors, without further stockholder approval, in the manner described herein (such final ratio, the “Reverse Stock Split Ratio”). If the Reverse Stock Split is effected, we would contemporaneously effect the Authorized Share Reduction. The par value per share of our common stock would remain unchanged at $0.0001. The following description of the Amendments is a summary and is subject to the full text of each of the proposed Amendment, a form of which is attached to this Proxy Statement as Annex A.

The Company is furnishing this Proxy Statement to its shareholders pursuant to and in accordance with the requirements of Section 13(e) of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and Rule 13e-3 under the Exchange Act, in connection with Leafly’s plan to effect a reverse stock split of our common stock, par value $0.0001 (“common stock”), with a view to reducing the number of record holders of our common stock to fewer than 300 and subsequently terminating the registration of our common stock under Section 12(g) of the Exchange Act and suspending our duty to file periodic reports and other information with the Securities and Exchange Commission (the “SEC”) under Section 15(d) of the Exchange Act, after which Leafly will no longer be subject to the public reporting obligations under federal securities laws, thereby “going private.”

Leafly may not consummate the reverse stock split described in this Proxy Statement until 20 days after the date on which it first mails this Proxy Statement.

QUESTIONS AND ANSWERS ABOUT THE PROPOSAL

Following are some questions about the Transaction and the related transactions that may be raised by our shareholders, and answers to each of those questions. The answers to the questions below may not include all the information that is important to you. You are urged to read carefully the entire Proxy Statement. In particular, for additional information, please see the information provided under “SPECIAL FACTORS” beginning on page viii.

Q: What are some of the advantages of the Transaction?

A: Our Board believes that the Transaction may have the following advantages, among others:

See the information under the captions “Special Factors — Purpose and Reasons for the Transaction” in this Proxy Statement.

Q: What are some of the disadvantages of the Transaction?

A: Our Board believes that the Transaction may have the following disadvantages, among others:

See the information under the caption “Special Factors — Effects of the Transaction — Potential Disadvantages of the Transaction to Shareholders” in this Proxy Statement.

Q: What are some of the factors that our Board considered in recommending approval of the Transaction?

A: In addition to the advantages and disadvantages described above, our Board considered numerous factors in recommending approval of the Transaction, including:

For a more comprehensive review of the factors considered by our Board, see the information under the caption “Special Factors” in this Proxy Statement.

Q: How did our Board determine the range for the Reverse Stock Split Ratio of 1 for 200 to 1 for 500? How will the Board determine the final Reverse Stock Split Ratio?

A: Our Board approved a range of ratios for the reverse split of 1 for 200 to 1 for 500, with the exact ratio to be set by the Company's Board of Directors within the above range in its sole discretion. The Board approved a range of ratios because the Board wanted the flexibility to choose a final ratio that would successfully reduce the number of shareholders of record to a number sufficiently below 300 that we would allow us to deregister pursuant to Section 12(g) of the Exchange Act and suspend our reporting obligations under Section 15(d) of the Exchange Act, as well as making it unlikely, in the future, to inadvertently increase our record holder base to 300 or more, and thus be required to once again file periodic reports and other information with the SEC. At the same time, the Board of Directors also is retaining the flexibility so that it can determine the ratio that can limit the cash resources expended in connection with the Transaction, while reducing the number of shareholder of record below the requisite threshold. If Proposal No. 3 is approved by our stockholders, the Board will make a determination as to the final Reverse Stock Split Ratio in light of the foregoing goal.

Q: What are the interests of our directors and executive officers in the Transaction?

A: As a result of the Transaction, we estimate that our directors and executive officers and their affiliated entities will increase their collective beneficial ownership of our common stock from approximately 6.9% to approximately 8.0%, depending on the final Reverse Stock Split Ratio and will receive approximately $400.00 in cash as a result of fractional shares, assuming the highest possible split of 1 for 500 split. To the contrary, however, the Transaction will also make it more difficult for directors and executive officers to sell their shares pursuant to Rule 144 promulgated under the Securities Act of 1934, as amended (the “Securities Act”). See the information under the caption “Other Matters Related to the Transaction — Potential Conflicts of Interest” in this Proxy Statement.

Q: How will the Transaction affect the day-to-day operations of Leafly?

A: The Transaction will have very little effect on Leafly’s business and operations, except to reduce management time spent on compliance and disclosure matters attributable to our Exchange Act filings, and may therefore enable management to increase its focus on managing our business and growing shareholder value. See the information under the caption “Special Factors — Effects of the Transaction” in this Proxy Statement.

Q: Should I send in my stock certificates now, and how will payment for shares be effected?

A: When the Transaction becomes effective:

See the information under the caption “Transaction Information — Structure of the Transaction — Exchange of Share Certificates for Cash Payment for Discontinued Stockholders” in this Proxy Statement.

Q: What if I hold common stock in “street name”?

A: If you hold common stock in “street name,” then your broker, bank or other nominee is considered the shareholder of record with respect to those shares and not you. We intend to treat shareholders holding our common stock in street name through a nominee (such as a broker, bank or other nominee) in the same manner as shareholders whose shares are registered in their own name. Accordingly, if the Ratio Number is set at 200, and if you hold 200 or more common stock in street name you will remain a shareholder after consummation of the Transaction. On the other hand, if the Ratio Number is set at 200, and if you hold fewer than 200 common stock in street name it is intended that you receive cash for your shares. However, it is also possible that the bank, broker or other nominee also holds shares for other beneficial owners of our common stock and that it may hold more than the Ratio Number shares of common stock in such capacity in the aggregate. Therefore, depending upon your nominee’s procedures, your nominee may not be

obligated to treat the Transaction as affecting its beneficial holders’ shares and you may not receive cash for your fractional interests. If you hold fewer than the Ratio Number of shares of common stock in street name, we encourage you to contact your bank, broker or other nominee directly as soon as possible so that arrangements can be made, if necessary, to register your holdings to ensure that you receive the cash payment of the Cash-Out Price per pre-Reverse Stock Split share. See the information under the caption “Special Factors — Effects of the Transaction” in this Proxy Statement.

While we are not aware of any fees or expenses that may be charged to “street name” holders by their brokers, banks or other nominees, we cannot guarantee that fees or expenses will not be charged to “street name” holders in connection with the Transaction.

Q: What if I hold a number of shares of common stock in through multiple brokerage or record accounts or a combination of brokerage and record accounts?

A: If you hold a total of shares of common stock divided up among multiple brokerage and/or record accounts, each with potentially fewer than the Ratio Number of shares, we urge you to contact your bank, broker or other nominee immediately to make arrangements to register and/or consolidate your holdings or take such other steps as may be necessary to avoid having your shares cashed out, to the extent you would like to retain your interest in Leafly. See the information under the caption “Special Factors — Effects of the Transaction” in this Proxy Statement.

Q: What information will I be able to get about Leafly if I continue to hold shares after the Transaction?

A: After the Transaction, we intend to provide the minimum amount of information required by Delaware law. We do not intend, but may in our discretion elect, to distribute press releases for material and other events. We will continue to hold shareholder meetings as required under Delaware law, our Certificate of Incorporation and our Bylaws, including annual meetings, or to take actions by written consent of our shareholders in lieu of meetings. See the information under the caption “Special Factors — Effects of the Transaction — Effects of the Transaction on Our Shareholders” in this Proxy Statement.

Q: What is the estimated maximum cost to cash out fractional shares?

A: Upon consummation of the Transaction, we estimate that a maximum of approximately $125,000 will be required to cash-out fractional shares as part of the Transaction. However, the amount actually paid in connection with the Transaction will depend on how many shares we are actually required to cash-out upon consummation of the Transaction and the Cash-Out Price ultimately determined. See the information under the caption “Other Matters Related to the Transaction — Source and Amounts of Funds” in this Proxy Statement.

Q: At what prices has our stock traded recently?

A: Effective January 17, 2025, Leafly common stock, par value $0.0001 per share, and warrants to purchase shares of Leafly common stock are currently traded on the OTC Pink Sheet Open Market and, between April 22, 2023 and January 17, 2025, on the Nasdaq Capital Market. From February 4, 2022 until April 21, 2023, Leafly common stock and warrants were traded on the Nasdaq Global Market, under the symbols LFLY and LFLYW, respectively. From November 7, 2019 until February 3, 2022, Leafly common stock and warrants traded on the Nasdaq Global Market under the trading symbols “MCMJ” and “MCMJW,” respectively.

On April 10, 2025 (the last trading date prior to the first public disclosure of the Transaction in the initial Preliminary Proxy Statement) the closing price of our common stock on OTC Pink Sheet Open Market was approximately $0.17. Following the initial filing of this Proxy Statement with the SEC on April 11, 2025, through May 8, 2025, the closing price of our common stock has ranged between $0.13 and $0.31 per share. See the information under the caption “Leafly Information — Company Securities” in this Proxy Statement.

Q: Am I permitted to trade my stock prior to the Transaction?

A: Shareholders are not prohibited from or restricted in trading their shares prior to the Transaction. However, the price of our common stock is volatile, in part because of the low volume of trading. This volatility may increase due to the announcement of the proposed Transaction. See the information under the caption “Special Factors — Effects of the Transaction” in this Proxy Statement.

Q: Will the Company effect the Reverse Stock Split without also effecting the Authorized Share Reduction? Or the Authorized Share Reduction without also effecting the Reverse Stock Split?

A: We will not effect the Reverse Stock Split without also effecting the Authorized Share Reduction, and vice versa.

Q: Is the Transaction contingent upon approval of any other proposal? Like Proposal No. 2 (Approval of Name Change)?

A: Proposal No. 3 (Approval of Amendment/Transaction) is not contingent upon the approval of any other proposal. The
determination by the Board of Directors and shareholders with respect to any other proposal, including Proposal No. 2 (Approval of
Name Change), is independent of any decision with respect to this Proposal No. 3 (Approval of Amendment/Transaction).

Q: Where can I find more information about Leafly?

A: We have filed certain information with the SEC. This information is available on the SEC’s website at www.sec.gov. See the information under the caption “Where You Can Find Additional Information” in this Proxy Statement. In addition, please see the information under the caption “Leafly Information.”

TRANSACTION INFORMATION

Background of the Transaction

On January 5, 2024, in connection with inbound interest from prospective strategic partners, our Board discussed the timing and logistics for potential transaction structures, financial models, assumptions and engagement of a financial advisor. The Board met again on January 19, 2024 to discuss the status of discussions with prospective strategic partners and further discussed the engagement of financial and legal advisors to aid their deliberations. The Board again, met on January 23, 2024 to take guidance from company counsel on their duties and obligations as directors and their duty of care in connection with any material transactions. The Board met again on January 26, 2024 to receive an update from Mr. Lee, a Company director and consultant at the time, on the status of discussions with prospective strategic partners.

On February 1, 9 and 16, 2024, Mr. Lee and Ms. Miyashita, the Company’s Chief Executive Officer and Director, provided an update to the Board on the status of discussions with prospective strategic partners and on the status of interviews with potential financial advisors. On February 23, 2024, the Board met again to discuss the importance of establishing a process prior to negotiating with counterparties and further discussed the sequencing of next steps required to establish such a process.

The Board met on March 8, 2024 to discuss the engagement of counsel in connection with establishing a strategic process. At a meeting of the Board on March 13, 2024, the Company’s General Counsel provided an update to the Board on the Company’s Nasdaq listing status, including an explanation of the compliance requirements to maintain its ongoing listing on the Nasdaq exchange. On March 22, 2024, the Company’s General Counsel updated the Board on the Company’s engagement of a legal advisor to advise it in connection with a strategic process, including to advise on matters related to the Company’s 2022 8.00% Convertible Senior Notes due 2025 (the “Notes”).

On April 9, 2024, the Company received a letter from the Nasdaq Staff (the “Notice”) notifying the Company that it no longer complied with Nasdaq's requirements for ongoing listing contained in Nasdaq Listing Rule 5550 for companies traded on the Nasdaq Capital Market. In April 2024, the Company also engaged in discussions with the holders of the Notes (the “debtholder”) with respect to potential modifications for the terms of the debt.

On April 16, 2024, Mr. Lee provided an update to the Board on the final financial advisor candidates, their fee proposals and scope of services. At the same meeting, the Board discussed potential for transactions with prospective strategic partners, as well as the status of discussions with the Company’s debtholder and determined to move forward with engaging a financial advisor to help with its deliberations. On April 29, 2024, Mr. Lee provided an additional update to the Board regarding ongoing discussions with the Company’s debtholder, including proposals by the debtholder with respect to restructuring the Notes. After considering the Company’s financial and strategic positioning and alternative opportunities, the Board determined not to accept the debtholder’s current proposal and agreed to retain PGP Capital Advisors LLP (“PGP”) and Benchmark Partners as the Company’s financial advisor. On May 10, 2024, the Board convened and met with the Company’s financial advisors, PGP and Benchmark.

On May 17, 2024, Ms. Miyashita provided the Board with an update regarding a non-binding acquisition proposal received from a potential third party strategic partner. The Board agreed that a response should be coordinated through the Company’s financial advisor, PGP. At a meeting on May 24, 2024, individuals from PGP provided the Board with a comprehensive overview of the proposed strategic process it would lead on behalf of the Company. The Company’s General Counsel also provided an update on the Company’s proposed compliance plan to come into compliance with Nasdaq’s ongoing listing requirements.

On June 21, 2024, individuals from PGP provided the Board with an update on the first phase of the strategic process, including outreach to potentially interested third parties. On June 28, 2024, PGP provided an update to the Board on the strategic process, including discussions with potential counterparties and the status of an investor presentation draft in development.

The Board met regularly throughout July and August to discuss the strategic process. On August 16, 2024, PGP provided an update to the Board on the status of the strategic process, including with respect to non-binding indications of interest received from prospective partners. On September 6, 2024, the Board discussed the potential timing and strategy for engaging with the Company’s debtholder to address the upcoming debt maturity in January 2025, and considered various restructuring options as an alternative to the ongoing strategic process. On September 13, 2024, Mr. Lee provided to the Board an update on his discussions with the Company’s debtholder and the Board again considered various restructuring options that may be available to it. On September 20, 2024, the Board met again to receive an update from PGP on its strategic process, as well as, discussing the potential to raise additional cash under the Company’s at-the-market offering. The Board again met on September 27, 2024 with its financial advisors and discussed potential terms with potential strategic partners and potential term sheet with the company’s debtholder.

On October 4, 2024, the Board met to discuss the status of discussions with prospective third parties, including the receipt of a non-binding indication of interest from a prospective partner. On October 11, 2024, the Board met with PGP to discuss the indication of interest received and the next steps to respond to such inquiry. On October 18, 2024, Ms. Miyashita relayed an update from PGP with respect to prospective financing and strategic partners. The Board also discussed the potential options, risks, benefits, strategies, barriers, costs and timing considerations in connection with a potential restructuring or extension of maturity of its debt. The Company’s General Counsel also provided an update to the Board on the potential to move to the OTC market if its appeal with the Nasdaq was unsuccessful and further provided an overview of the requirements to deregister as a reporting company with the SEC.

On November 1, 2024, the Board received guidance on its fiduciary duties in the case of insolvency. PGP also led a discussion of a term sheet received from a prospective strategic partner and the Board discussed an appropriate counterproposal. On November 15, 2024, management provided to the Board an update on discussions with the Company’s debtholder. PGP also provided an update on discussions with other prospective strategic partners. The Board also heard an update on the upcoming appeal hearing regarding the Company’s Nasdaq listing on December 5, 2024. On November 22, 2024, Mr. Lee provided to the Board an update on his discussions with the Company’s debtholder and on negotiations with the third party who had submitted an offer at the start of the month. The Board considered, among other things, the costs associated with a potential transaction, and discussed an appropriate counteroffer to the third party. In addition to the counteroffer, the Board discussed developing a term sheet to share with the debtholder that would provide for an amendment to existing debt terms and extension of the maturity date.

On December 6, 2024, Mr. Lee and Mr. Pickerill provided an update on their recent conversation with the Company’s debtholder. The Company’s General Counsel also presented an update on the Nasdaq hearing regarding the Company’s appeal that had occurred on December 5, 2024. On December 13, 2024, Mr. Lee provided an update on discussions with a prospective strategic partner and also shared the offer received from the Company’s debtholder, which included an offer to extend the debt maturity by 120 days. On December 16, 2024, the Board discussed the offer from the Company’s debtholder and considered the terms for a counteroffer, taking into consideration the impacts to Leafly’s business operations and employees. On the same day, the management team presented its first draft of its operating budget for 2025, including details regarding the potential cost-savings that would come from deregistering as a public company (“Go Dark”). Management presented its first draft of a 2025 operating budget to the Board, with potential cost savings that could be achieved, assuming the Company would be able to Go Dark as of March 31, 2025. The Board asked the management team to refine its 2025 financial projections, including a request to refine the cost estimates in the event of a Go Dark scenario for consideration at a follow-up meeting in January 2025. The Board also instructed Management to explore the alternative methods for reducing the number of holders of records, such as refined counting methodologies, tender offers, reverse stock splits, or any other method by which the numbers of holders of record could be reduced, and asked Management to report back with respect to the feasibility of such methods, the costs associated with such methods and the impacts of the various alternatives.

Through December 2024, the Company continued discussions with the Company’s debtholder. On December 31, 2024, in connection with the Board’s consideration of financial covenants that the debtholder was requiring, the management provided projected financials, outlining expected expenses and savings occurring from a Go Dark effective date of March 30, 2025.

On January 3, 2025, the Board discussed ongoing negotiations with the Company’s debtholder, including the requested cash covenants and minimum levels of cash required to wind-down the Company in the event of a foreclosure. Ms. Miyashita also provided an update on the Nasdaq hearing panel’s decision, noting that an extension had been granted until April 2, 2025, contingent upon the company completing an equity transaction described in the Company’s presentation to Nasdaq on December 5, 2024. Acknowledging that the Company would be unable to complete such a transaction by the required timeline, Ms. Miyashita agreed to communicate such inability to Nasdaq through the company’s Nasdaq advisor.

Again on January 7, 2025, the Board together with management considered the minimum cash covenant requested by the debtholder, while considering the costs savings projected in connection with a Go Dark transaction. Management updated the Board with respect to its further pursuit of methods by which to Go Dark, identifying which methods were unlikely to be successful and the reasons success was unlikely. Ms. Miyashita then discussed the Nasdaq determination letter and shared guidance that the Company should notify Nasdaq of its inability to achieve necessary milestones outlined in the Nasdaq’s letter. The Board agreed that a Form

8-K notification would be filed if the Nasdaq responded with an official delisting determination following notification from the Company that it would not meet specified milestones.

On January 15, 2025, the Company entered into an amendment (the “Debt Amendment”) with the Company’s debtholder to modify the terms of that certain Note Purchase Agreement, dated January 11, 2022 (the “Note Purchase Agreement”), relating to the Company’s Notes. Concurrently with the Debt Amendment to the Note Purchase Agreement, the Company entered into an amended and restated note (the “Amended and Restated Note”) for the Notes. The Debt Amendment and the Amended and Restated Note, among other things, (i) extended the maturity date of the Notes from January 31, 2025 to July 1, 2025 and (ii) added certain financial maintenance covenants. In addition, the Company has agreed to pay down 12.5% of the outstanding principal of the Notes and all accrued and unpaid interest on the Notes since the last interest payment date on July 31, 2024. The prepayment and interest payment was made on January 21, 2025. In connection with the Amendment, the Company also granted the holders of the Notes a security interest in the Company’s assets as collateral to secure the Company’s obligations underlying the Notes, subject to certain exceptions and limitations.

Also on January 15, 2025, the Company received written notification (the “Delisting Notice”) from The Nasdaq Stock Market LLC (“Nasdaq”) that the Nasdaq Hearings Panel (the “Panel”) had determined to delist the Company’s common stock and warrants and suspend trading of the securities at the open of trading on January 17, 2025. As a result of the delisting, the Company’s common stock and warrants began trading publicly on the OTC Pink Open Market under its existing symbols “LFLY” and “LFLYW,” respectively.

On January 28, 2025, the Board met again with the management team to finalize the operating plan and budget for 2025. In discussing expense assumptions for the operating plan, management again highlighted the monthly expense and cash forecast assuming the Company would be able to achieve cost savings associated with a Go Dark transaction. The Board discussed with management their progress with respect to alternatives for a means to Go Dark. Management provided updates with respect to discussions they had with potential outside counsel to pursue a reverse stock split as a Go Dark transaction. The Board requested that management further refine its cost estimates for a Go Dark scenario.

On March 5, 2025, the Board met with the Company's outside counsel, to receive an overview of the Go Dark process assuming a reverse stock split, as outlined in a memorandum prepared by outside counsel and distributed to the Board members prior to the meeting, and to review counsel’s guidance on the potential impacts from undertaking a Go Dark transaction, including an assessment of the Company’s contractual obligations to third parties, prospective impacts to future equity offerings both for the Company and its shareholders and impacts to the Company’s existing securities offerings registered with the SEC. Outside counsel gave a presentation to the Board regarding a detailed step plan for deregistration, a timeline for executing a Go Dark transaction, and an outline of further Board and management actions required for the Go Dark transaction. The Board of Directors authorized management to move forward assuming the use of a reverse stock split as the means to Go Dark. At this meeting, outside counsel also initiated conversations with the Board regarding the considerations for identifying the appropriate ratio for the reverse stock split and the appropriate amount for cash payments in lieu of fractional shares under the current General Corporation Law of the State of Delaware (“DGCL”). Outside counsel reminded the Board that under the DGCL, the corporation has several options for the treatment of fractional shares in a stock split if the corporation chooses not to issue fractions of a share as a result of a stock split, including arranging for the disposition of fractional interests by those entitled thereto or paying in cash the fair value of fractions of a share as of the time when those entitled to receive such fractions are determined. The Board discussed with management the options available with respect to fractional shares, as well as potential methodologies for setting the “fair value” of fractional shares.

The Board met, again, with outside counsel and management on March 10, 2025, to discuss the filing of post-effective amendments to the Company’s S-3 and S-8 registrations, which would be necessary to effect a Go Dark transaction in the 2025 calendar year. The Board again discussed the risks and benefits of a Go Dark transaction.

On March 12, 2025, the Company filed post-effective amendments to terminate its active registration statements, which were later declared effective by the SEC. At a Board meeting on March 12, 2025, Mr. Lee provided an update on his discussions with the Company’s debtholder. At a meeting of the Company’s Audit Committee, at which all Board members were present, management provided an updated forecast for 2025, which included the Go Dark cost and savings assumptions.

On April 1, 2025, the Board, with outside counsel in attendance, was presented again with the Go Dark process overview and discussed the potential reverse stock split ratio and payments for fractional shares. Management provided a presentation to the Board with information regarding the estimated impact of a range of ratios on the number of holders of record, based on recent information regarding holdings of holders of record, as well as the estimated range for the aggregate amounts of cash payments at various ratios at a theoretical cash-out price of $0.25 per share which reflected a premium to recent trading prices. The Board discussed the results of the Company’s marketing process in 2024, the net book value per share, and recent and historical trading prices per share. The Board noted that the fair value per share to shareholders indicated by the 2024 marketing process would be less than zero, and the net book value per share was negative. The Board approved the Reverse Stock Split and determined a range of potential reverse stock split ratios to submit

for stockholder approval, with the final ratio to be determined by the Board. The Board determined to defer their decision with respect to the cash-out price, and requested further information with respect to setting the fair value to be paid for fractional shares.

At the same meeting, the Board also approved a reduction in the number of authorized shares of the Company to save costs associated with Delaware franchise taxes. The Board discussed various considerations of fair value of the fractional shares, as set forth in greater detail under “SPECIAL FACTORS” above, and asked management to revert with additional estimates of fair value to finalize its fair value for fractional shares prior to filing the preliminary proxy.

Independent director Alan Pickerill resigned from the Board effective April 1, 2025, after the above-referenced meeting. His resignation was not the result of any disagreement with the Company.

On April 9, 2025, the Board met to review the proposed disclosures and disclosure requirements with respect to Proposal 3, and to set the fair value of the fractional shares. Management provided an additional presentation to the Board regarding various value considerations. The Board further discussed these valuation considerations, including updated information regarding recent trading prices and volumes, as well as whether a fairness opinion was necessary or appropriate. The Board considered the impact of the reverse stock split on stockholders that would be cashed out, stockholders that would continue to hold shares, the officers and directors of the Company, and the Company as a whole. After reviewing materials prepared by management illustrating the cash-out price based on a per share cash-out price of $0.25 up to $0.40 per share, and after reviewing updated trading prices that had further declined since they last reviewed trading prices at the April 1, 2025 meeting, The Board narrowed the range for potential cash-out prices to $0.25 per share to $0.30 per share, and directed management to conduct further analysis on the fair value based on trading information for an additional few days.

On April 11, 2025, after receipt of additional information from management about the proposed per share cash-out price based on updated trading information since the last meeting, the Board of Directors executed a written consent authorizing the fair value to be used as the Cash-Out Price at $0.28 per share of common stock.

Material Terms

Our Board has authorized the Reverse Stock Split, in order to reduce the number of record holders of our common stock to fewer than 300. As a result of the Reverse Stock Split, Discontinued Shareholders (i.e., those holding fewer than the Ratio Number pre-Reverse Stock Split shares as of the effective date of the Reverse Stock Split) will have no further interest in Leafly, will no longer be shareholders of Leafly and will become entitled to receive only a cash payment equal to the $0.28 multiplied by the number of pre-Reverse Stock Split shares owned by them. Continuing Shareholders (i.e. those holding the Ratio Number or more pre-Reverse Stock Split shares as of the effective date of the Reverse Stock Split) will continue to be shareholders of Leafly after the Reverse Stock Split.

The Board believes that stockholder approval of a range of potential reverse stock split ratios is in the best interests of our Company and stockholders because it is not possible to predict the number of record holders and market conditions at the time a Reverse Stock Split would be implemented. We believe that a range of Reverse Stock Split Ratios provides us with the most flexibility to achieve the desired results of the Reverse Stock Split. The Reverse Stock Split Ratio to be selected by our Board will be not more than 1 for 500 or less than 1 for 200.

The selection of the specific Reverse Stock Split Ratio will be based on several factors, including, among other things:

We believe that granting our Board the authority to set the Reverse Stock Split Ratio is essential because it allows us to take these factors into consideration and to react to changing market conditions. If the Board chooses to implement the Reverse Stock Split, the Company will make a public announcement regarding the determination of the Reverse Stock Split Ratio.

The Board of Directors, taking into such considerations as described in greater detail under “Fairness of Transaction” below, has determined that the Cash-Out Price for the shares will be equal to $0.28 per share.

As a result of the Reverse Stock Split, we anticipate that the number of our common stock issued and outstanding will be reduced from 3,137,382 (the number outstanding as of May 9, 2025) to range of approximately 5,000 to 6,000.

We estimate that the total cash to be paid to Discontinued Shareholders will be approximately $125,000. In addition, the expenses incurred to effect the Transaction are estimated to be $190,000. These expenses are expected to be paid out of our currently available cash. The fractional shares acquired in the Transaction will be cancelled and returned to the status of authorized but unissued common stock.

We intend to file with the SEC a Form 15 to deregister our common stock as soon as practicable after the consummation of the Transaction. Upon the filing of the Form 15, our obligation to file periodic and current reports (i.e., Forms 10-K, 10-Q and 8-K) under the Exchange Act will be immediately suspended. Deregistration of our common stock will be effective 90 days after filing of the Form 15. During the 90 days prior to the effectiveness of the deregistration of our common stock, we will remain subject to the proxy solicitation rules under Section 14 of the Exchange Act, and our shareholders will remain subject to the beneficial ownership reporting and short swing profit disgorgement rules under Section 16 of the Exchange Act, as well as the beneficial ownership reporting rules under Section 13 of the Exchange Act. Upon deregistration of our common stock, our obligation to comply with the requirements of the proxy rules and to file proxy statements under Section 14 of the Exchange Act will also be terminated. We will not be required to file periodic reports with the SEC in the future unless we subsequently file another registration statement under the Securities Act or again have record holders of our common stock in excess of 300 on the first day of a subsequent fiscal year.

Under the current General Corporation Law of the State of Delaware (“DGCL”), approval of the Reverse Stock Split proposal requires the approval of holders of a majority of the outstanding stock of the Company entitled to vote thereon and, to the extent applicable, by holders of a majority of the outstanding stock of each class of stock entitled to vote as a separate class. The Series A Preferred Stock, which will be voted on the Amendment to mirror the votes cast by the common stock, was issued to address the increasing challenge faced by many corporations in obtaining stockholder approval by a majority of outstanding shares for a reverse stock split, given that many outstanding shares of public companies are held by brokers and other record holders in “street name” and was issued solely for purposes of assisting the Company in obtaining the majority of outstanding vote requirement needed to approve the Reverse Stock Split. If a majority of the votes cast by the holders of the common stock at the Annual Meeting are cast in favor of the Reverse Stock Split, the Series A Preferred Stock should amplify those votes in such a way to reach the threshold required by the DGCL for the Reverse Stock Split.

Reasons for the Reduction in the Authorized Number of Shares of Common Stock and Preferred Stock

As a matter of Delaware law, implementation of the Reverse Stock Split does not require a change in the total number of shares of our common stock and preferred stock authorized under our Certificate of Incorporation. However, the proposed reduction in the total number of authorized shares of our common stock and preferred stock is designed to reduce certain of our costs, especially with respect to the Delaware franchise taxes. The Company’s Certificate of Incorporation authorizes the issuance of up to (a) 200,000,000 shares of common stock and (b) 5,000,000 shares of preferred stock, which currently results in the Company paying $200,000 per year in Delaware franchise taxes. As of May 9, 2025, the Company only had 3,137,382 shares of common stock outstanding and one share of preferred stock outstanding, and no immediate plans to issue additional shares of common stock or preferred stock. The number of outstanding shares will be further reduced as a result of the Reverse Stock Split. A reduction in the number of authorized shares to 5,000,000 shares of common stock and 1,000,000 shares of preferred stock would reduce the amount payable by the Company in the form of Delaware franchise taxes to $51,000 per year, a projected cost savings of $149,000 per year.

Effects of the Authorized Share Reduction

The authorized share reduction will have no effect on the Company or the stockholders, either financially or with respect to their rights and obligations with respect to their common stock. The only impact on the Company would be that the reduction in authorized shares will limit the number of shares the Company can issue in the future without seeking shareholder approval. Our board of directors believes that after the Authorized Share Reduction, the number of shares of common stock available for future issuance is sufficient for current anticipated future needs.

Structure of the Transaction

The Transaction consists of a Reverse Stock Split (including a cash payment in lieu of receipt of a fractional share to a shareholder holding fewer than the Ratio Number of pre-Reverse Stock Split shares). Assuming the Reverse Stock Split is approved at the Annual Meeting, the effective date of the Reverse Stock Split will be June 11, 2025 or such later date as determined by our Board. On the effective date of the Reverse Stock Split, each shareholder of record will receive one share of common stock for every Ratio Number of pre-Reverse Stock Split shares held in his or her account as of such date. Any shareholder of record who holds fewer than the Ratio Number of pre-Reverse Stock Split shares in his or her account at the time of the Reverse Stock Split will receive a Cash-Out Price per pre-Reverse Stock Split share and will no longer be a shareholder of Leafly after the Transaction.

We intend for the Transaction to treat shareholders holding common stock in street name through a nominee (such as a bank or broker) in the same manner as shareholders whose shares are held of record in their own names, and nominees will be instructed to

effect the Transaction for their beneficial holders. However, nominees may have different procedures and shareholders holding shares in street name should contact their nominees.

In general, the Transaction can be illustrated by the following examples, assuming a Reverse Stock Split Ratio of 1 for 200 (though there is no assurance that the Reverse Stock Split Ratio would be 1 for 200):

Example 1. A shareholder holds 150 common stock in his account before the effective date of the Reverse Stock Split. Instead of receiving a fractional share of our common stock immediately after the Reverse Stock Split, the shareholder’s shares will be converted into the right to receive cash. The shareholder would receive $42.00 ($0.28 x 150 shares). Note: If the shareholder wants to continue the investment in Leafly, before the effective date of the Reverse Stock Split, the shareholder can buy at least 50 more shares. The shareholder would have to act far enough in advance of the Reverse Stock Split so that the purchase is completed and the additional shares are credited in his account by the effective date.

Example 2. A shareholder holds 1,500 common stock as of the effective date of the Reverse Stock Split. After the Reverse Stock Split, the shareholder will hold seven shares of common stock, and receive $28.00 ($0.28 x 100 shares) for the remaining fraction of a share.

Example 3. A shareholder has two separate accounts. As of the effective date of the Reverse Stock Split, the shareholder holds 100 common stock in one account and 150 common stock in the other. If we can determine that the two separate accounts belong to the same person (based upon the name of the account and the social security number associated with the account), then we will treat the two accounts as a single account. Accordingly, the shareholder will be treated as having more than 250 pre-Reverse Stock Split shares. In the Reverse Stock Split, the shareholder’s stock will be converted into 1 share of common stock. We will cash out the shareholder’s 0.25 post-Reverse Stock Split fractional shares, representing 50 pre-Reverse Stock Split shares for $14.00.

If, however, we are unable to determine that the two separate accounts belong to the same person, then the shareholder will receive cash payments equal to the Cash-Out Price of the common stock in each account. In this case, the shareholder would receive two checks totaling $70.00 ($0.28 x 100 shares = $28.00; $0.28 x 150 shares = $42.00). Note: If the shareholder wants to be certain to continue as a shareholder in Leafly, the shareholder can consolidate or transfer two accounts before the effective date of the Reverse Stock Split into an account with at least 200 pre-Reverse Stock Split shares. Alternatively, the shareholder can buy at least 100 more shares for the account with 100 common stock and 50 more shares for the account with 150 common stock, and hold them in such shareholder’s respective accounts. The shareholder would have to act far enough in advance of the Reverse Stock Split so that the consolidation or the purchase is completed by the effective date.

Example 4. A shareholder holds 150 common stock in street name in a brokerage account as of the effective date of the Reverse Stock Split. We intend for the Transaction to treat shareholders holding shares of our common stock in street name through a nominee (such as a bank or broker) in the same manner as shareholders whose shares are registered in their names. Nominees will be instructed to effect the Transaction for their beneficial holders. If this occurs, the shareholder will receive, through the shareholder’s broker, a check for $42.00 ($0.28 x 150 shares). However, nominees may have a different procedure and shareholders holding shares of our common stock in street name should contact their nominees.

Exchange of Share Certificates for Cash Payment for Discontinued Stockholders

As soon as practicable after the effective date, holders of fewer than the Ratio Number shares will be notified and sent a letter of transmittal and instructed how to transmit their certificates representing common stock to the Exchange Agent. Upon proper completion and execution of the letter of transmittal, and the return of the letter of transmittal and accompanying share certificate(s), each shareholder entitled to receive payment will receive payment as outlined in the letter of transmittal. Shareholders should allow for approximately five business days after mailing for our exchange agent to receive the letter of transmittal and accompanying stock certificate and approximately seven to 10 business days following our exchange agent’s receipt of properly completed materials for payment to be made. In the event we are unable to locate a shareholder, or if a shareholder fails to properly complete, execute and return the letter of transmittal and accompanying stock certificate any funds payable to such shareholder pursuant to the Transaction will be held by our exchange agent until a proper claim is made, subject to applicable abandoned property laws. Holders of fewer than the Ratio Number shares of common stock on the effective date of the Reverse Stock Split will receive in exchange a cash payment in the amount of the Cash-Out Price per pre-Reverse Stock Split share.

No service charges or expenses will be payable by shareholders in connection with the exchange of certificates for cash, except for service charges or expenses, if any, imposed by your nominee. In the event that any certificate representing common stock is not presented, the applicable cash payment will be administered in accordance with the relevant state abandoned property laws. Until the cash payments have been delivered to the appropriate public official pursuant to the abandoned property laws, such payments will be paid to the holder of the eligible certificate or his, her or its designee, without interest, at such time as the common stock have been properly presented for exchange.

Exchange of Share Certificates of Continuing Shareholders

As soon as practicable after the effective date, Continuing Shareholders will be sent a letter of transmittal explaining how they can exchange their certificates representing the number of common stock they held prior to the Transaction for new share certificates representing the number of whole common stock they hold after the Transaction. To the extent a Continuing Stockholder holds fractional shares immediately after the Reverse Stock Split, that Continuing Stockholder will be entitled to receive a cash payment for those fractional shares from the exchange agent at the Cash-Out Price. No service charges or expenses will be payable by Continuing Shareholders in connection with the Reverse Stock Split, except for service charges or expenses, if any, imposed by your nominee. Upon proper completion and execution of the letter of transmittal, and the return of the letter of transmittal and accompanying share certificate(s), each Continuing Shareholder entitled to receive payment in connection with the Reverse Stock Split will receive payment as outlined in the letter of transmittal. Shareholders should allow for approximately five business days after mailing for our exchange agent to receive the letter of transmittal and accompanying stock certificate and approximately seven to 10 business days following our exchange agent’s receipt of properly completed materials for payment to be made and a new share certificate to be issued. In the event we are unable to locate a Continuing Shareholder, or if a Continuing Shareholder fails to properly complete, execute and return the letter of transmittal and accompanying share certificate, any funds payable to such shareholder pursuant to the Reverse Stock Split will be held by our Exchange Agent until a proper claim is made, subject to applicable abandoned property laws.

If a Continuing Shareholder fails to exchange such Continuing Shareholders pre-Transaction share certificate in accordance with the letter of transmittal, then such pre-Transaction share certificate shall be deemed to represent the number of whole common stock held by the Continuing Shareholder as a result of the Transaction.

Recommendation and Voting

The Board of Directors unanimously recommends in favor of the Transaction. Our directors and executive officers have indicated that they intend to vote all of the shares of our common stock held or controlled by them (223,318 shares of common stock) “FOR” the Transaction.

In addition, Ms. Miyashita currently holds one share of Series A Preferred Stock, which will have 100,000,000 votes, but has the right to vote only on any proposal involving a reverse stock split and/or a decrease in the number of authorized shares of common stock, like Proposal No. 3, and until such time as a such proposal is approved by the stockholders, and will have no voting rights except (i) with respect to such proposal in which its votes are cast for and against such proposal in the same proportion as shares of common stock are voted for and against such proposal (with any shares of common stock that are not voted, whether due to abstentions, broker non-votes or otherwise not counted as votes for or against the Reverse Stock Split proposal) and (ii) unless the holders of shares of outstanding capital stock representing a majority of the voting power of all outstanding shares of capital stock of the Company are present, in person or by proxy, at the meeting of stockholders at which a such proposal is submitted for stockholder approval (or any adjournment thereof). The share of Series A Preferred Stock will vote together with the common stock as a single class on any Proposal No. 3. The Series A Preferred Stock has no other voting rights, except as may be required by the General Corporation Law of the State of Delaware.

Prior to the issuance of the Series A Preferred Stock, stockholder approval of an Amendment and Transaction like that described by Proposal No. 3 required the affirmative approval of a majority of the voting power of the outstanding shares of common stock. Following the issuance of the Series A Preferred Stock, stockholder approval of Proposal No. 3 requires affirmative approval from a majority of the voting power of the shares of common stock and the share of Series A Preferred Stock, voting together as a single class. Ms. Miyashita will cast the votes represented by the share of Series A Preferred on Proposal No. 3 in a manner that mirrors the votes cast by holders of common stock on such proposal. Prior to the issuance of the share of Series A Preferred Stock, abstentions and any other non-votes would have had the same effect as a vote against Proposal No. 3. Following the issuance of the share of Series A Preferred Stock, abstentions and any other non-votes on Proposal No. 3 will still technically have the same effect as a vote against such proposal, but because the share of Series A Preferred has a high number of votes and will vote in a manner that mirrors votes actually cast by the holders of common stock (which does not include abstentions or any other non-votes), abstentions and any other non-votes will have no effect on the manner in which the Series A Preferred Stock votes are cast.

Reservation

Although our Board has approved the Transaction and subsequent termination of registration of our common stock under the Exchange Act and suspension of our duty to file periodic reports and other information with the SEC thereunder, our Board reserves the right to abandon, postpone or modify the Transaction and such termination and suspension at any time before they are consummated for any reason. A number of factors or circumstances could cause our Board to abandon, postpone or modify the Transaction and such deregistration and suspension, including, without limitation, the following:

If we abandon, postpone or modify the Transaction, we will issue a press release and File a Form 8-K or, if required by law, mail information to our shareholders, informing our shareholders of any such change (“Notice”). In the event we change the terms of the Transaction, including the effective date of the Transaction, but still intend to complete the Transaction, we will provide Notice at least 10 days prior to the effective date (or the new effective date if the effective date is postponed) of the Transaction.

Each share of common stock is entitled to one vote. The single outstanding share of Series A Preferred Stock is entitled to 100,000,000 votes, but only on Proposal No. 3 and such votes will be voted as to mirror the votes of the common stock, as discussed in greater detail above under “Recommendation and Voting.” Once a quorum has been established, the affirmative vote of the holders of a majority of the voting power of the common stock and the Series A Preferred Stock of the Company, voting together as a single class, represented in person or by proxy at the meeting is required to approve the Amendment necessary to effectuate the Transaction.

If your broker holds your shares in its name and does not receive voting instructions from you with respect to Proposal No. 3 related to the Transaction, your broker does not have discretionary voting power for those particular items. Therefore, if you are a beneficial owner and do not provide your broker with voting instructions, your shares may constitute broker non-votes with respect to the Proposal No. 3.

No Appraisal or Dissenters’ Rights

No appraisal or dissenters’ rights are available to our shareholders who dissent from the Transaction are provided under Delaware law our Certificate of Incorporation or our bylaws.

Change Related to Board of Directors Composition

There are no plans to change the composition of the Board of Directors in connection with the Transaction.

In addition, if a partnership holds our Common Stock, the tax treatment of a partner generally will depend on the status of the partner and upon the activities of the partnership. Accordingly, partnerships which hold our Common Stock and partners in such partnerships should consult their tax advisors.

YOU ARE URGED TO CONSULT YOUR TAX ADVISOR WITH RESPECT TO THE APPLICATION OF THE UNITED STATES FEDERAL INCOME TAX LAWS TO YOUR PARTICULAR SITUATION, AS WELL AS ANY TAX CONSEQUENCES OF THE PURCHASE, OWNERSHIP AND DISPOSITION OF OUR COMMON STOCK ARISING UNDER THE UNITED STATES FEDERAL ESTATE OR GIFT TAX RULES OR UNDER THE LAWS OF ANY STATE, LOCAL, FOREIGN OR OTHER TAXING JURISDICTION OR UNDER ANY APPLICABLE TAX TREATY.

Leafly Holdings, Inc.

We believe that the Reverse Stock Split will constitute a reorganization as described in Section 368(a)(1)(E) of the Code. Accordingly, we will not recognize taxable income, gain or loss in connection with the Reverse Stock Split.

Stockholders

The federal income tax consequences of the Reverse Stock Split for our stockholders will differ depending on the number of shares of pre-split common stock owned and, in some cases, constructively owned by such stockholders. As set forth in more detail below, stockholders who own at least the Ratio Number of shares of pre-split common stock will retain their shares and will not recognize any gain, loss or dividend income as a result of the Reverse Stock Split. Stockholders who own fewer than the Ratio Number of shares of pre-split Common Stock will receive cash, the treatment of which will depend on whether the constructive ownership rules described below are applicable. If such constructive ownership rules do not apply, a stockholder who owns fewer than the Ratio Number of shares of pre-split common stock generally will recognize gain or loss upon the sale or exchange of the pre-split common stock. If such constructive ownership rules apply, the stockholder may be required to treat any cash received as a dividend distribution rather than as gain or loss from a sale or exchange, as more fully described below. The differences in tax consequences to the stockholders do not depend on whether a stockholder is an affiliate of the Company, has voted to approve the Reverse Stock Split or is an unaffiliated stockholder. Neither the differences in tax consequences between stockholders who hold at least the Ratio Number of shares of pre-split common stock and stockholders who own fewer than the Ratio Number of shares of pre-split common stock nor the differences in tax consequences between the stockholders and the Company were reasons for the Company to undertake the Reverse Stock Split in this form at this time.

Stockholders Who Receive Shares of Post-Split Common Stock

A stockholder who retains shares of post-split common stock in the transaction (i.e., a stockholder who owns at least the Ratio Number of shares of pre-split common stock) will not recognize gain or loss or dividend income as a result of the Reverse Stock Split with respect to their continuing shares, and the tax basis (as adjusted for the Reverse Stock Split) and holding period of such stockholder in shares of pre-split common stock will carry over as the tax basis and holding period of such stockholder’s shares of post-split common stock.

Stockholders Who Receive Cash

The cash received by stockholders in the Reverse Stock Split will be treated as having such shares redeemed in a taxable transaction governed by Section 302 of the Code and, depending on a stockholder’s situation, the transaction will be taxed as either:

Amounts treated as gain or loss from the sale or exchange of redeemed shares will be capital gain or loss. Amounts treated as a taxable dividend are ordinary income to the recipient; however, a corporate taxpayer (other than an S corporation) may be allowed a dividends received deduction subject to applicable limitations and other special rules.

Under Section 302 of the Code, a redemption of shares from a stockholder as part of the Reverse Stock Split will be treated as a sale or exchange of the redeemed shares if:

These three tests (the “Section 302 Tests”) are applied by taking into account not only shares that a stockholder actually owns, but also shares that the stockholder constructively owns pursuant to Section 318 of the Code. Under the constructive ownership rules of Section 318 of the Code, a stockholder is deemed to constructively own shares owned by certain related individuals and entities in which the stockholder has an interest in addition to shares directly owned by the stockholder. For example, an individual stockholder is considered to own shares owned by or for his or her spouse and his or her children, grandchildren and parents (“family attribution”). In addition, a stockholder is considered to own a proportionate number of shares owned by estates or certain trusts in which the stockholder has a beneficial interest, by partnerships in which the stockholder is a partner, and by corporations in which 50% or more in value of the stock is owned directly or indirectly by or for such stockholder. Similarly, shares directly or indirectly owned by beneficiaries of estates of certain trusts, by partners of partnerships and, under certain circumstances, by stockholders of corporations may be considered owned by these entities (“entity attribution”). A stockholder is also deemed to own shares which the stockholder has the right to acquire by exercise of an option or by conversion or exchange of a security. Constructively owned shares may be reattributed to another taxpayer. For example, shares attributed to one taxpayer as a result of entity attribution may be attributed from that taxpayer to another taxpayer through family attribution.

A stockholder who receives cash in the Reverse Stock Split (i.e., owns fewer than the Ratio Number of shares of pre-split Common Stock) and does not constructively own any shares of post-split common stock will have his or her interest in the Company completely terminated by the Reverse Stock Split and will therefore receive sale or exchange treatment on his or her pre-split common stock. That is, such a stockholder will recognize gain or loss equal to the difference between the cash payment and the stockholder’s tax basis for his or her shares of pre-split common stock.

A stockholder who receives cash in the Reverse Stock Split and would only constructively own shares of post-split common stock as a result of family attribution may be able to avoid constructive ownership of the shares of post-split common stock by waiving family attribution and, thus, be treated as having had his or her interest in the Company completely terminated by the Reverse Stock Split. Among other things, waiving family attribution requires (i) that the stockholder have no interest in the Company (including as an officer, director, employee or stockholder) other than an interest as a creditor and does not acquire such an interest during the ten-year period immediately following the Reverse Stock Split other than stock acquired by bequest or inheritance and (ii) including an election to waive family attribution in the stockholder’s tax return for the year in which the Reverse Stock Split occurs.

A stockholder who receives cash in the Reverse Stock Split and immediately after the Reverse Stock Split constructively owns shares of post-split common stock must compare (i) his, her or its percentage ownership immediately before the Reverse Stock Split (i.e., the number of voting shares actually or constructively owned by him, her or it immediately before the Reverse Stock Split divided by the number of voting shares outstanding immediately before the Reverse Stock Split) with (ii) his, her or its percentage ownership immediately after the Reverse Stock Split (i.e., the number of voting shares constructively owned by his, her or it immediately after the Reverse Stock Split divided by the number of voting shares outstanding immediately after the Reverse Stock Split).

If the stockholder’s post-Reverse Stock Split ownership percentage is less than 80% of the stockholder’s pre-Reverse Stock Split ownership percentage, the receipt of cash is “substantially disproportionate” with respect to the stockholder, and the stockholder will, therefore, receive sale or exchange treatment on the portion of his, her or its shares of pre-split Common Stock exchanged for cash in lieu of fractional shares.

If the receipt of cash by a stockholder fails to constitute an “exchange” under the “substantially disproportionate” test or the “complete termination” test, the receipt of cash may constitute an “exchange” under the “not essentially equivalent to a dividend” test. The receipt of cash by a stockholder will be “not essentially equivalent to a dividend” if the transaction results in a “meaningful reduction”

of the stockholder’s proportionate interest in the Company. If (i) the stockholder exercises no control over the affairs of the Company (e.g., is not an officer, director or high ranking employee), (ii) the stockholder’s relative stock interest in the Company is minimal, and (iii) the stockholder’s post-Reverse/ Forward Stock Split ownership percentage is less than the stockholder’s pre-Reverse/ Forward Stock Split ownership percentage, the receipt of cash will generally not be essentially equivalent to a dividend with respect to the stockholder and the stockholder will, therefore, receive sale or exchange treatment on the portion of his, her or its shares of pre-split common stock exchanged for cash in lieu of fractional shares.

In all other cases, cash in lieu of fractional shares received by a stockholder who immediately after the Reverse Stock Split constructively owns shares of post-split common stock will be treated: (i) first, as a taxable dividend to the extent of allocable earnings and profits, if any; (ii) second, as a tax-free return of capital to the extent of the stockholder’s tax basis in the redeemed shares; and (iii) finally, as gain from the sale or exchange of the redeemed shares.

Backup Tax Withholding

We are required to furnish to the holders of common stock, other than corporations and other exempt holders, and to the IRS, information with respect to dividends paid on the common stock.

You may be subject to backup withholding with respect to proceeds received from a disposition of the shares of common stock. Certain holders (including, among others, corporations and certain tax-exempt organizations) are generally not subject to backup withholding. You will be subject to backup withholding if you are not otherwise exempt and you (a) fail to furnish your taxpayer identification number (“TIN”), which, for an individual, is ordinarily his or her social security number; (b) furnish an incorrect TIN; (c) are notified by the IRS that you have failed to properly report payments of interest or dividends; or (d) fail to certify, under penalties of perjury, that you have furnished a correct TIN and that the IRS has not notified you that you are subject to backup withholding. Backup withholding is not an additional tax but, rather, is a method of tax collection. You generally will be entitled to credit any amounts withheld under the backup withholding rules against your United States federal income tax liability provided that the required information is furnished to the IRS in a timely manner.

Source and Amounts of Funds

Based on estimates of the record ownership of shares of our common stock, the number of shares of our common stock outstanding and other information as of April 10, 2025, and assuming that approximately 447,000 pre-Reverse Stock Split shares of our common stock are cancelled in the Reverse Stock Split (which in the aggregate constitute less than 15% of our common stock outstanding before the Reverse Stock Split), Leafly estimates that the total funds required to consummate the Transaction will be approximately $315,020. Approximately $125,000 of this amount will be used to pay the consideration for fractional shares of our common stock resulting from the Reverse Stock Split and approximately $190,000 will be used to pay the costs of the Transaction, estimated as follows:

Final costs of the Transaction may be more or less than the estimates shown above. Leafly expects to pay the costs of the Transaction, including the amounts to be paid to shareholders holding fewer than the Ratio Number of shares of our common stock, out of our currently available cash.

LEAFLY INFORMATION

Leafly

Leafly’s mission is to help people discover cannabis. We endeavor to serve as the world’s most trusted destination to discover and shop for legal cannabis. The Company was founded in 2010 with the objective to demystify cannabis, a product that lived in the shadows through decades of prohibition. Tens of millions of unique visitors access Leafly each year to learn more about legal cannabis, discover

what products are right for them, and to shop with regulation-compliant local businesses. Through helping people navigate their cannabis journey, Leafly helps millions of consumers discover the benefits of cannabis.

Leafly began as a platform to provide consumers with trusted cannabis information. Since then, Leafly has evolved into a content-first, community-driven, multi-sided marketplace that connects consumers to cannabis brands and licensed retailers. We offer cannabis retailers and brands subscription-based marketplace listings that provide our broad-based cannabis audience with information, reviews, menus, and ordering and delivery options through legal retailers. Our audience — which was over 70 million in 2023 — chooses Leafly for our unique, original content and data.

On February 4, 2022 (the “Closing Date”), we consummated a business combination in connection with that certain Agreement and Plan of Merger, dated as of August 9, 2021 and amended on September 8, 2021 (as may be amended, restated, supplemented or otherwise modified from time to time, the “Merger Agreement”), by and among Merida (as defined below), Merger Sub I (as defined below), Merger Sub II (as defined below) and Leafly Holdings, Inc., a Washington corporation (“Legacy Leafly”). Pursuant to the Merger Agreement and in connection therewith, at the Closing, among other things, (i) Merger Sub I merged with and into Legacy Leafly (the “Initial Merger”), with Legacy Leafly being the surviving entity (the “Initial Surviving Company”) of the Initial Merger and Legacy Leafly’s shareholders receiving Common Stock, in exchange for their equity securities of Legacy Leafly, and (ii) immediately following the Initial Merger and as part of the same overall transaction as the Initial Merger, the Initial Surviving Company merged with and into Merger Sub II (the “Final Merger” and, together with the Initial Merger, the “Mergers”), with Merger Sub II surviving the Final Merger as a limited liability company named Leafly, LLC (the “Final Surviving Company”). In connection with the Closing, the registrant changed its name from “Merida Merger Corp. I” to “Leafly Holdings, Inc.” As a result of the foregoing business combination (the “Business Combination”) and such name change, Legacy Leafly became a wholly owned subsidiary of the Company, with the securityholders of Legacy Leafly becoming securityholders of the Company.

Our principal executive offices are located at 600 1st Avenue, Suite 330, PMB 88154, Seattle, Washington.

Going Concern Status

Under the rules of ASC Subtopic 205-40 “Presentation of Financial Statements — Going Concern” (“ASC 205-40”), reporting companies are required to evaluate whether conditions and/or events raise substantial doubt about their ability to meet their future financial obligations as they become due within one year after the date that the financial statements are issued. This evaluation takes into account a company’s current available cash and projected cash needs over the one-year evaluation period but may not consider things beyond its control. At December 31, 2024, we had $29.4 million of 2022 Notes (defined below) which were scheduled to mature on January 31, 2025 and were modified on January 15, 2025 and extended to July 1, 2025, contingent upon a 12.5% reduction in principal that was paid on January 21, 2025. Based on its current liquidity position the Company would not be able to repay the 2022 Notes when due. In addition, as noted above, the Company has experienced revenue declines, incurred recurring operating losses, used cash from operations, and relied on the capital raised in the Business Combination to continue ongoing operations. The Company has incurred operating losses since its inception and had an accumulated deficit of $79.9 million and $74.2 million at December 31, 2024 and 2023, respectively. These conditions, when considered in the aggregate, raise substantial doubt about the Company’s ability to continue as a going concern within one year of the date that its 2024 financial statements are issued.

The Company’s management is closely monitoring and reducing operating expenses where it is able to, while ensuring the trajectory and viability of the business remains intact. However, the Company cannot meet its debt maturity obligations without a significant capital infusion or a lender’s commitment to refinance the debt. After considering all available evidence, Leafly’s management determined that the combined impact of the cost reduction measures, Leafly’s current negative working capital of $17.9 million as of December 31, 2024 and planned operations will not be sufficient to meet the Company’s capital requirements for a period of at least twelve months from the date that these December 31, 2024 financial statements are issued and that substantial doubt exists about Leafly’s ability to continue as a going concern. Management will continue to evaluate our liquidity and capital resources.

Our ability to continue as a going concern may depend on our ability to raise additional funds, which we may seek to do through equity or debt financings, or seek to refinance the 2022 Notes. As substantial doubt about our ability to continue as a going concern exists, our ability to raise additional funds through the sale and issuance of equity or debt securities or through bank or other financing could be substantially impaired. There can be no assurance that we will be able to raise additional funds or have access to bank or other financings or even if we have access to such financing, that it will be available on terms commercially acceptable to the Company. If we raise funds by issuing debt securities or preferred stock, or by incurring loans, these forms of financing would have rights, preferences, and privileges senior to those of holders of our common stock. If adequate capital is not available to us when needed, or in the amounts required, we may be forced to terminate, significantly curtail or cease our operations or to pursue other strategic alternatives, including bankruptcy, which may not be available to us. Our consolidated results of operations could be materially adversely affected by these decisions and shareholders could lose all of your investment in the Company.

Company Securities

Shares Issued and Outstanding

The following description summarizes the material terms of the securities of Leafly Holdings, Inc. registered under Section 12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”): (1) common stock and (2) Warrants to purchase common stock. This summary does not purport to be complete and is qualified by reference to the provisions of Leafly’s Second Amended and Restated Certificate of Incorporation, as amended (the “Certificate of Incorporation”), Amended and Restated Bylaws, as amended (the “Bylaws”), Amended and Restated Registration Rights Agreement, dated February 4, 2022, by and among Leafly and certain stockholders of Leafly (the “Registration Rights Agreement”), and the Warrant Agreement, dated November 4, 2019, by and between Merida and Continental Stock Transfer & Trust Company (the “Warrant Agreement”), which are incorporated by reference as exhibits to the Annual Report on Form 10-K, and to the applicable provisions of Delaware law.

Authorized and Outstanding Stock

Leafly’s authorized capital stock consists of:

Reverse Stock Split

On July 12, 2023,during the Company’s 2023 Annual Meeting of Stockholders, Leafly’s stockholders approved a proposal for a reverse stock split (the “2023 Reverse Stock Split”) as part of the Company’s plan to regain compliance with the Bid Price Requirement under Nasdaq listing rules. Effective September 12, 2023, the Company effected a one-for-twenty (1-for-20) reverse stock split of its common stock. As a result of the 2023 Reverse Stock Split, Leafly issued approximately 34,192 shares under the provisions of the Reverse Stock Split and no fractional shares were issued in connection with the 2023 Reverse Stock Split. All shares and share prices herein have been updated accordingly to reflect the impact of the 2023 Reverse Stock Split.

Voting Rights

Except as otherwise required by law or the Certificate of Incorporation, the holders of Leafly common stock exclusively possess all stockholder voting power with respect to Leafly. Holders of Leafly common stock are entitled to one vote per share on each matter properly submitted to a vote of stockholders. The holders of Leafly common stock will at all times vote together as one class on all matters submitted to a vote of stockholders, unless otherwise required by Delaware law or the Certificate of Incorporation.

Dividend Rights

Subject to the rights, if any, of the holders of any outstanding series of the Leafly Preferred Stock, the holders of Leafly common stock are entitled to receive dividends and other distributions (payable in cash, property or capital stock of Leafly) when, as and if declared by the Leafly Board of Directors out of any assets or funds legally available and will share equally on a per share basis in such dividends and distributions

No Preemptive or Similar Rights

Leafly common stock is not entitled to preemptive rights, and is not subject to conversion, redemption or sinking fund provisions.

Liquidation, Dissolution and Winding Up

Subject to the rights, if any, of the holders of any outstanding shares of Leafly Preferred Stock, in the event of any voluntary or involuntary liquidation, dissolution or winding-up, after payment or provision for payment of the debts and other liabilities of Leafly, the holders of Leafly common stock will be entitled to receive all the remaining assets of Leafly available for distribution to its stockholders, ratably in proportion to the number of shares of the Leafly common stock held by them.

Leafly Preferred Stock

Blank Check Preferred

The Leafly Board of Directors is authorized, subject to limitations prescribed by the law of the State of Delaware, to issue Leafly Preferred Stock from time to time in one or more series. The Leafly Board of Directors is authorized to establish the number of shares to be included in each such series and to fix the voting rights, if any, designations, powers, preferences and relative, participating, optional, special and other rights, if any, and any qualifications, limitations and restrictions thereof, applicable to the shares of each series. The Leafly Board of Directors is able, without stockholder approval, to issue Leafly Preferred Stock with voting and other rights that could adversely affect the voting power and other rights of the holders of the Leafly common stock and could have anti-takeover effects. The ability of the Leafly Board of Directors to issue Leafly Preferred Stock without stockholder approval could have the effect of delaying, deferring or preventing a change of control of Leafly or the removal of existing management.

Series A Preferred Stock

On April 1, 2025, in connection with the Subscription Agreement, the Company filed a Certificate of Designation of Series A Preferred Stock (the “Series A Certificate of Designation”) with the Secretary of State of the State of Delaware. The Series A Certificate of Designation designates one share of the Company’s preferred stock as Series A Preferred, and establishes and designates the preferences, rights and limitations thereof. The Series A Certificate of Designation became effective upon filing.

Convertibility. The share of Series A Preferred is not convertible into, or exchangeable for, shares of any other class or series of stock or other securities of the Company.

Dividends. The share of Series A Preferred shall not be entitled to receive dividends.

Voting. The share of Series A Preferred will have 100,000,000 votes, but has the right to vote only on any Reverse Stock Split proposal and until such time as a Reverse Stock Split proposal is approved by the stockholders, and will have no voting rights except (i) with respect to a Reverse Stock Split proposal in which its votes are cast for and against such Reverse Stock Split proposal in the same proportion as shares of common stock are voted for and against such Reverse Stock Split proposal (with any shares of common stock that are not voted, whether due to abstentions, broker non-votes or otherwise not counted as votes for or against the Reverse Stock Split proposal) and (ii) unless the holders of shares of outstanding capital stock representing a majority of the voting power of all outstanding shares of capital stock of the Company are present, in person or by proxy, at the meeting of stockholders at which a Reverse Stock Split proposal is submitted for stockholder approval (or any adjournment thereof). The share of Series A Preferred will vote together with the Common Stock as a single class on any Reverse Stock Split proposal. The Series A Preferred has no other voting rights, except as may be required by the General Corporation Law of the State of Delaware.

Rank; Liquidation. Upon a liquidation, bankruptcy, reorganization, merger, acquisition, sale, dissolution or winding up of the Company, whether voluntarily or involuntarily, pursuant to which assets of the Company or consideration received by the Company are to be distributed to the stockholders, the holder of Series A Preferred will be entitled to receive, before any payment is made to the holders of common stock by reason of their ownership thereof, an amount equal to $100.00.

Transfer Restrictions. The Series A Preferred may not be transferred at any time prior to stockholder approval of a Reverse Stock Split proposal without the prior written consent of the Board.

Redemption. The outstanding share of Series A Preferred will be redeemed in whole, but not in part, for a redemption price of $100.00, payable out of funds lawfully available therefor, upon the earlier of (i) any time such redemption is ordered by the Board in its sole discretion, automatically and effective on such time and date specified by the Board in its sole discretion, or (ii) automatically immediately following the approval by the stockholders of the Company of a Reverse Stock Split proposal.

Warrants

Each whole Warrant entitles the registered holder to purchase 0.05 shares of Leafly common stock at a price of $230.00 per share, subject to adjustment as discussed below. The Warrants will expire on at 5:00 p.m., New York City time on the date that is five years after the Closing Date, or earlier upon redemption or liquidation. In addition to the Warrants, Merida sold private warrants to Merida Holdings, LLC and EarlyBirdCapital in connection with Merida’s initial public offering. The private warrants are identical to the Warrants except that the private warrants are exercisable for cash or on a cashless basis, at the holder’s option, and will not be redeemable by Leafly, in each case so long as they are still held by Merida Holdings, LLC, EarlyBirdCapital, or their permitted transferees. Leafly may call the Warrants for redemption (excluding the private warrants), in whole and not in part, at a price of $0.20 per Warrant in the following circumstances:

The redemption criteria for the Warrants have been established at a price which is intended to provide Warrant holders a reasonable premium to the initial exercise price and provide a sufficient differential between the then-prevailing share price and the Warrant exercise price so that if the share price declines as a result of our redemption call, the redemption will not cause the share price to drop below the exercise price of the Warrants. However, the price of the shares of Leafly common stock may fall below the $360.00 trigger price as well as the $230.00 Warrant exercise price after the redemption notice is issued.

If Leafly calls the Warrants for redemption as described above, Leafly’s management will have the option to require all holders that wish to exercise Warrants to do so on a “cashless basis.” In such event, each holder would pay the exercise price by surrendering the Warrants for that number of shares of Leafly common stock equal to the quotient obtained by dividing (a) the product of the number of shares of Leafly common stock underlying the Warrants, multiplied by the difference between the exercise price of the Warrants and the “fair market value” (defined below) by (b) the fair market value. The “fair market value” for this purpose will mean the average reported last sale price of the shares of Leafly common stock for the five trading days ending on the third trading day prior to the date on which the notice of redemption is sent to the holders of Warrants.

The Warrants are issued in registered form under a Warrant Agreement between Continental Stock Transfer & Trust Company, as Warrant Agent, and Leafly. The Warrant Agreement provides that the terms of the Warrants may be amended without the consent of any holder to cure any ambiguity or correct any defective provision, or to add or change any other provisions with respect to matters or questions arising under the Warrant Agreement as Leafly and the Warrant Agent may deem necessary or desirable and that they, relying on the advice of counsel, deem shall not adversely affect the interest of the registered holders. The Warrant Agreement requires the approval, by written consent or vote, of the holders of at least 50% of the then outstanding Warrants (including the private warrants) in order to make any change that adversely affects the interests of the registered holders. Notwithstanding the foregoing, Leafly may lower the exercise price of the Warrants or extend the duration of the exercise period without the consent of the registered holders.

The exercise price and number of shares of Leafly common stock issuable on exercise of the Warrants may be adjusted in certain circumstances including in the event of a stock dividend, extraordinary dividend or our recapitalization, reorganization, merger or consolidation. However, except as described below, the Warrants will not be adjusted for issuances of shares of Leafly common stock at a price below their respective exercise prices.

The Warrants may be exercised upon surrender of the Warrant Certificate on or prior to the expiration date at the offices of the Warrant Agent, with the exercise form on the reverse side of the Warrant Certificate completed and executed as indicated, accompanied by full payment of the exercise price, by certified or official bank check payable to us, for the number of Warrants being exercised. The Warrant holders do not have the rights or privileges of holders of shares of Leafly common stock and any voting rights until they exercise their Warrants and receive shares of Leafly Common Stock. After the issuance of shares of Leafly common stock upon exercise of the Warrants, each holder will be entitled to one vote for each share held of record on all matters to be voted on by stockholders.

No Warrants will be exercisable for cash unless we have an effective and current registration statement covering the shares of Leafly common stock issuable upon exercise of the Warrants and a current prospectus relating to such shares of Leafly common stock. Under the terms of the Warrant Agreement, we have agreed to use our best efforts to meet these conditions and to file and maintain a current and effective prospectus relating to the Leafly common stock issuable upon exercise of the Warrants until the expiration of the Warrants. However, we cannot assure you that we will be able to do so. If a registration statement covering the shares of Leafly common stock issuable upon exercise of the Warrants is not effective within 90 days of the Closing Date, Warrant holders may, until such time as there is an effective registration statement and during any period when we shall have failed to maintain an effective registration statement, exercise Warrants on a cashless basis pursuant to the exemption provided by Section 3(a)(9) of the Securities Act, provided that such

exemption is available. If that exemption, or another exemption, is not available, holders will not be able to exercise their Warrants on a cashless basis.

Warrant holders may elect to be subject to a restriction on the exercise of their Warrants such that an electing Warrant holder would not be able to exercise their Warrants to the extent that, after giving effect to such exercise, such holder would beneficially own in excess of 9.8% of the shares of Leafly common stock outstanding.

No fractional shares will be issued upon exercise of the Warrants. If, upon exercise of the Warrants, a holder would be entitled to receive a fractional interest in a share, we will, upon exercise, round up to the nearest whole number the number of shares of Leafly common stock to be issued to the Warrant holder.

Anti-Takeover Provisions

Some provisions of Delaware law, the Certificate of Incorporation, and the Bylaws contain provisions that could make the following transactions more difficult: an acquisition of Leafly by means of a tender offer; an acquisition of Leafly by means of a proxy contest or otherwise; or the removal of incumbent officers and directors. It is possible that these provisions could make it more difficult to accomplish or could deter transactions that stockholders may otherwise consider to be in their best interest or in Leafly’s best interests, including transactions that provide for payment of a premium over the market price for Leafly’s shares.

These provisions, summarized below, are intended to discourage coercive takeover practices and inadequate takeover bids. These provisions are also designed to encourage persons seeking to acquire control of Leafly to first negotiate with the Leafly Board of Directors. We believe that the benefits of the increased protection of Leafly’s potential ability to negotiate with the proponent of an unfriendly or unsolicited proposal to acquire or restructure Leafly outweigh the disadvantages of discouraging these proposals because negotiation of these proposals could result in an improvement of their terms.

Delaware Law

Leafly is subject to the provisions of Section 203 of the DGCL regulating corporate takeovers. In general, Section 203 prohibits a publicly held Delaware corporation from engaging in a business combination with an interested stockholder for a period of three years following the date on which the person became an interested stockholder unless:

Generally, a business combination includes a merger, asset or stock sale, or other transaction or series of transactions together resulting in a financial benefit to the interested stockholder. An interested stockholder is a person who, together with affiliates and associates, owns or, within three years prior to the determination of interested stockholder status, did own 15% or more of a corporation’s outstanding voting stock. We expect the existence of this provision to have an anti-takeover effect with respect to transactions the Leafly Board of Directors does not approve in advance. We also anticipate that Section 203 may discourage attempts that might result in a premium over the market price for the shares of Leafly common stock held by stockholders.

Certificate of Incorporation and Bylaws provisions

The Certificate of Incorporation and Bylaws include a number of provisions that could deter hostile takeovers or delay or prevent changes in control of Leafly’s management team, including the following:

While the Delaware courts have determined that such choice of forum provisions are facially valid, a stockholder may nevertheless seek to bring a claim in a venue other than those designated in the exclusive forum provisions. In such instance, we would expect to vigorously assert the validity and enforceability of the exclusive forum provisions of the Bylaws. This may require significant additional costs associated with resolving such action in other jurisdictions and there can be no assurance that the provisions will be enforced by a court in those other jurisdictions.

Other Agreements with Respect to the Company’s Securities

Series A Preferred Stock

On April 1, 2025, the Company entered into a Subscription Agreement (the “Subscription Agreement”) with Yoko Miyashita, the Chief Executive Officer of the Company, pursuant to which the Company agreed to issue and sell one share of the Company’s newly designated Series A Preferred Stock, par value $0.0001 per share (the “Series A Preferred”), to Ms. Miyashita for a purchase price of $100.00.

Pursuant to the Subscription Agreement, Ms. Miyashita has agreed to cast the votes represented by the share of Series A Preferred on any Reverse Stock Split proposal in the same proportion as shares of common stock of the Company are voted (excluding any shares of common stock that are not voted, whether due to abstentions, broker non-votes or otherwise) on such Reverse Stock Split proposal; provided, that unless and until at least 33 1∕3 % of the outstanding shares of common stock on the record date established for the meeting of stockholders at which the Reverse Stock Split proposal is presented are present in person or represented by proxy at such meeting, Ms. Miyashita will not vote the share of Series A Preferred on such Reverse Stock Split proposal.

Registration Rights

At the closing of the Business Combination, the Company entered into the Registration Rights Agreement, attached as an exhibit to this Annual Report on Form 10-K, with the registration rights holders. Pursuant to the terms of the Registration Rights Agreement, (a) any (i) outstanding share of Leafly common stock or any private warrants, and (ii) shares of Leafly common stock issued as Earnout Shares (as defined below) to shareholders of Legacy Leafly that received shares of Leafly common stock in the Business Combination or issuable as Earnout Shares pursuant to the Earnout Plan (as defined below) and (b) any other equity security of Leafly issued or issuable with respect to any such share of Leafly common stock by way of a stock dividend or stock split or in connection with a combination of shares, recapitalization, merger, consolidation or other reorganization or otherwise, are entitled to registration rights. The Registration Rights Agreement provides that Leafly will, as soon as reasonably practicable, but in any event within 30 days after the consummation of the transactions contemplated by the Merger Agreement, subject to extensions as set forth in the Registration Rights Agreement, file with the SEC a shelf registration statement registering the resale of the registration rights holders shares and will use its commercially reasonable best efforts to cause such registration statement to be declared effective as soon as practicable after the filing thereof, but in no event later than 60 days following the filing deadline, subject to extensions as set forth in the Registration Rights Agreement. Merida Holdings, LLC, EarlyBirdCapital, and their transferees may demand not more than three demand registrations or shelf underwritten offerings in the aggregate and not more than two demand registrations in any twelve-month period, and the shareholders of Legacy Leafly that received shares of Leafly common stock in the Business Combination may demand not more than six demand registrations or shelf underwritten offerings in the aggregate and not more than two demand registrations in any twelve-month period, and Leafly will not be obligated to participate in more than four demand registrations or shelf underwritten offerings, in any twelve-month period. Leafly will bear the expenses incurred in connection with the filing of any registration statements filed pursuant to the terms of the Registration Rights Agreement.

2022 Notes

Merida entered into a $30,000,000 convertible note purchase agreement (the “Note Purchase Agreement”) in January 2022, which Legacy Leafly subsequently guaranteed and joined as a party to the agreement on February 4, 2022 in connection with the Business Combination (the “2022 Notes”). Accordingly, post-Business Combination, the 2022 Notes are presented as a liability on Leafly’s balance sheet, net of debt issuance costs and debt discount. The 2022 Notes bear interest at 8% annually (with an effective interest rate

of 9.91% for the year ended December 31, 2024), paid in cash semi-annually in arrears on July 31 and January 31 of each year, and were scheduled to mature on January 31, 2025.

The 2022 Notes were unsecured convertible senior notes due 2025. They are convertible at the option of the holders at any time before maturity at an initial conversion share price of $250.00 per $1,000 principal amount of 2022 Notes and per $1,000 of accrued but unpaid interest on any converted 2022 Notes. In addition, the Company may, at its election, force the conversion of the 2022 Notes on or after January 31, 2024, if the volume-weighted average trading price of the Company’s common stock exceeds $360.00 for at least 20 trading days (whether or not consecutive) during a period of 30 consecutive trading days. The Company also has the option, on or after January 31, 2023 and prior to the 40th trading day immediately before the maturity date and subject to the holders’ ability to optionally convert, to redeem all or a portion of the 2022 Notes at a cash redemption price equal to 100% of the principal amount of the 2022 Notes, plus accrued and unpaid interest, if any. The holders of the 2022 Notes have the right to cause the Company to repurchase for cash all or a portion of the 2022 Notes held by such holder upon the occurrence of a “fundamental change” (as defined in the Note Purchase Agreement) or in connection with certain asset sales, in each case at a price equal to 100% of par plus accrued and unpaid interest, if any.

2023 and 2024 Partial Conversions

On December 19, 2023, the Company and each of the 2022 Note holders executed a notice of conversion and consent (the “Conversion Notice”) to effect a temporary and limited adjustment to the conversion price under the Note. Pursuant to the Conversion Notice, the conversion price under the Note was equal to the dollar amount that was 5% less than the last reported sale price of the Company’s common stock on the trading day prior to the date of the Conversion Notice, or $4.978 (the “Conversion Price Adjustment”). The Conversion Price Adjustment was available for a period of five business days from the date of the Conversion Notice or until conversion requests for up to $300,000 were received, whichever was earlier. On December 19, 2023, one holder tendered a conversion request for $300,000 at the Conversion Price Adjustment, resulting in the issuance of an aggregate of 60,265 shares of common stock and a corresponding reduction in the outstanding amount of the 2022 Notes of $300,000. Following such tender and in accordance with the terms of the Conversion Notice, the Conversion Price Adjustment was terminated.

On May 7, 2024, the Company and each of the 2022 Note holders executed a notice of conversion and consent (the “Second Conversion Notice”) to effect a temporary and limited adjustment to the conversion price under the 2022 Notes. Pursuant to the Second Conversion Notice, the conversion price under the 2022 Notes was equal to the dollar amount that was 5% less than the last reported sale price of the Company’s common stock on the trading day prior to the date of the Second Conversion Notice, or $2.8405 (the “Second Conversion Price Adjustment”). The Second Conversion Price Adjustment was available for a period of five business days from the date of the Second Conversion Notice or until conversion requests for up to $275,000 were received, whichever was earlier. On May 7, 2024, one holder tendered a conversion request for $275,000 at the Second Conversion Price Adjustment, resulting in the issuance of an aggregate of 96,813 shares of common stock and a corresponding reduction in the outstanding amount of the 2022 Notes of $275,000. Following such tender and in accordance with the terms of the Conversion Notice, the Conversion Price Adjustment was terminated. The Company shall pay applicable accrued interest payable and owing on the converted amount through the effective date of the conversion in accordance with the terms of the 2022 Notes in cash on the next interest payment date.

Debt Modification

On January 15, 2025, the Company entered into an amendment (the “Debt Amendment”) to the terms of the Note Purchase Agreement, relating to the 2022 Notes. Concurrently with the Debt Amendment, the Company entered into an amended and restated note (the “Amended and Restated Note”) for the 2022 Notes. The Debt Amendment and the Amended and Restated Note, among other things, (i) extended the maturity date of the 2022 Notes from January 31, 2025 to July 1, 2025 and (ii) added certain financial maintenance covenants. In addition, the Company agreed to pay down 12.5% of the outstanding principal of the Notes and all accrued and unpaid interest on the Notes since the last interest payment date on July 31, 2024. Accordingly, the prepayment of $3,678,000 and interest payment of $1,118,000 occurred on January 21, 2025. In connection with the Debt Amendment, the Company also granted the holders of the 2022 Notes a security interest in the Company’s assets as collateral to secure the Company’s obligations underlying the 2022 Notes, subject to certain exceptions and limitations.

The aforementioned new financial maintenance covenants required by the Debt Amendment include primarily:

Equity Incentive Plans

Our employees are eligible to receive equity-based awards at the discretion of the Compensation Committee of the Board of Directors under our 2021 Equity Incentive Plan. Prior to the Business Combination, employees received grants of stock options under our 2018 Equity Incentive Plan.

2021 Plan

The 2021 Plan became effective immediately upon closing of the Business Combination. Pursuant to the 2021 Plan, 225,125 shares of common stock were initially reserved for issuance. During the term of the 2021 Plan, the number of shares of common stock thereunder automatically increases on each January 1, commencing on January 1, 2023, and ending on (and including) January 1, 2031, by the lesser of (i) 10% of the fully diluted shares of common stock as of the last day of the preceding fiscal year and (ii) 225,125 shares (adjusted pursuant to the terms of the 2021 Plan). Effective January 1, 2025, 270,436 shares of common stock were available for issuance under the 2021 Plan and 45,312 remained available at December 31, 2024.

2018 Plan

The 2018 Plan became effective on April 17, 2018. The 2018 Plan terminated upon closing of the Business Combination in 2022, but then-outstanding options under the 2018 Plan remain outstanding pursuant to their terms, with adjustments to the number of shares and exercise prices to reflect the terms of the Business Combination.

Market Information

Effective January 17, 2025, our common stock, par value $0.0001 per share, and warrants to purchase shares of our common stock are currently traded on the OTC Pink Sheet Open Market and, since April 22, 2023, on the Capital Market. Any over-the-counter market quotations on the OTC Pink Sheet Open Market reflect inter-dealer prices, without retail mark-up, mark-down or commission and may not necessarily represent actual transactions. From February 4, 2022 until April 21, 2023, our common stock and warrants were traded on the Nasdaq Global Market, under the symbols LFLY and LFLYW, respectively. From November 7, 2019 until February 3, 2022, our common stock and warrants traded on the Nasdaq Global Market under the trading symbols “MCMJ” and “MCMJW,” respectively.

The high and low sales price per common share as reported on the consolidated reporting system are set forth below for the periods indicated.

Holders

The aggregate number of stockholders of record as of May 1, 2025 was 432.

Dividend Policy

We have never paid any cash dividends on our common stock. We anticipate that we will retain funds and future earnings to support operations and to finance the growth and development of our business. Therefore, we do not expect to pay cash dividends in the foreseeable future. Any future determination to pay dividends will be at the discretion of our board of directors and will depend on our financial condition, results of operations, capital requirements and other factors that our board of directors deems relevant. Moreover, the terms of our outstanding convertible notes restrict our ability to pay dividends, and any additional debt we or any of our subsidiaries may incur in the future may include similar restrictions.

Selling Securityholders. The Shelf Offering was terminated, and all unsold securities removed from registration pursuant to a post-effective amendment to the Registration Statement on Form S-3, which became effective March 13, 2025.

In connection with the Shelf Offering, on June 27, 2024, the Company entered into an Equity Distribution Agreement (the “Equity Distribution Agreement”) with The Benchmark Company, LLC (the “Agent”) pursuant to which the Company could sell (the “ATM Offering”), at its option, up to an aggregate of $2,519,000 in shares of Leafly common stock through the Agent and, as of December 31, 2024, $1,266 remained unsold under this limit. The ATM Offering was made pursuant to the Shelf Offering by methods deemed to be “at the market,” as defined in Rule 415 promulgated under the Securities Act of 1933, as amended. The Company agreed to pay the Agent a commission in cash equal to 3% of the gross proceeds from the sale of shares in the ATM Offering. The offering of shares pursuant to the Equity Distribution Agreement has been terminated in accordance with its terms. The Company has agreed to reimburse the Agent for the fees and disbursements of its counsel, payable upon execution of the Equity Distribution Agreement, in an amount not to exceed $50,000 in connection with the establishment of this at-the-market offering program, in addition to certain ongoing fees of its legal counsel. During the year ended December 31, 2024, the Company sold 470,000 shares of common stock at an average price of $2.42 per share and raised gross proceeds totaling $1,137,000 under the ATM Offering including commissions of $34,000. In addition, during the year ended December 31, 2024, the Company incurred $195,000 of costs in connection with launching its ATM Offering.

The Company has also previously registered the offer and sale of securities issued with respect to its 2021 Equity Incentive Plan and 2018 Equity Incentive Plan as follows:

Prior Stock Purchases

The Company has not purchased any of its common stock or warrants in the past two years.

Recent Transactions in Our Common Stock

Except as disclosed in the Proxy Statement and as set forth below, in the last 60 days, there have been no transactions in our common stock by any of our officers or directors and, to our knowledge, by any person controlling us or any of such person’s associates.

Since February 1, 2025, the following vestings occurred with respect to previous grants under the 2021 Equity Incentive Plan: