<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0508</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2025-02-27</periodOfReport>

    <issuer>
        <issuerCik>0001785592</issuerCik>
        <issuerName>Leafly Holdings, Inc. /DE</issuerName>
        <issuerTradingSymbol>LFLY</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001900428</rptOwnerCik>
            <rptOwnerName>Krishnaswamy Suresh</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>113 CHERRY STREET</rptOwnerStreet1>
            <rptOwnerStreet2>PMB 88154</rptOwnerStreet2>
            <rptOwnerCity>SEATTLE</rptOwnerCity>
            <rptOwnerState>WA</rptOwnerState>
            <rptOwnerZipCode>981042205</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>false</isDirector>
            <isOfficer>true</isOfficer>
            <isTenPercentOwner>false</isTenPercentOwner>
            <isOther>false</isOther>
            <officerTitle>CFO</officerTitle>
        </reportingOwnerRelationship>
    </reportingOwner>

    <aff10b5One>false</aff10b5One>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2025-02-27</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>A</transactionCode>
                <equitySwapInvolved>false</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>1646</value>
                    <footnoteId id="F1"/>
                </transactionShares>
                <transactionPricePerShare>
                    <value>0.2205</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>A</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>41374</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2025-02-27</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>F</transactionCode>
                <equitySwapInvolved>false</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>489</value>
                    <footnoteId id="F2"/>
                </transactionShares>
                <transactionPricePerShare>
                    <value>0.2205</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>40885</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <footnotes>
        <footnote id="F1">Represents a multi-year performance-stock unit (&quot;PSU&quot;) award granted to the reporting person in 2022 (the &quot;2022 PSUs&quot;) under the Issuer's 2021 Equity Incentive Plan (&quot;Plan&quot;). The 2022 PSUs are split into three tranches of 1,646 PSUs each (&quot;Tranche I&quot;, &quot;Tranche II&quot;, or &quot;Tranche III&quot;), with the number of PSUs eligible to vest conditioned on the achievement of certain performance targets established by the Compensation Committee (the &quot;Committee&quot;) of the Issuer's Board of Directors for specified annual performance periods. The number of PSUs eligible to vest in Tranche III for the calendar year &quot;2024 Performance Period&quot; was conditioned on the Issuer's achievement of certain Committee-approved cash balance targets as of December 31, 2024 (the &quot;Tranche III Goals&quot;). On February 27, 2025, the Committee certified the Issuer's maximum achievement of the Tranche III Goals, resulting in the vesting of 100% of the 2022 PSUs applicable to Tranche III, as reported.</footnote>
        <footnote id="F2">Represents shares withheld by the Issuer to satisfy withholding taxes due in connection with the vesting of the 2022 PSUs applicable to Tranche III as described in Note 1, at a net settlement priceequal to the closing stock price on February 27, 2025.</footnote>
    </footnotes>

    <ownerSignature>
        <signatureName>/s/ Yoko Miyashita, as attorney-in-fact for Suresh Krishnaswamy</signatureName>
        <signatureDate>2025-03-07</signatureDate>
    </ownerSignature>
</ownershipDocument>
