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      <filer>
        <filerCredentials>
          <cik>0001816299</cik>
          <ccc>XXXXXXXX</ccc>
        </filerCredentials>
      </filer>
      <liveTestFlag>LIVE</liveTestFlag>



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    <issuerInfo>
      <issuerCik>0001691421</issuerCik>
      <issuerName>Lemonade, Inc.</issuerName>
      <secFileNumber>001-39367</secFileNumber>
      <issuerAddress>
        <com:street1>5 CROSBY STREET</com:street1>
        <com:street2>3RD FLOOR</com:street2>
        <com:city>NEW YORK</com:city>
        <com:stateOrCountry>NY</com:stateOrCountry>
        <com:zipCode>10013</com:zipCode>
      </issuerAddress>
      <issuerContactPhone>(844) 733-8666</issuerContactPhone>
      <nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>Peters John Sheldon</nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>
      <relationshipsToIssuer>
        <relationshipToIssuer>Officer</relationshipToIssuer>
      </relationshipsToIssuer>
    </issuerInfo>
    <securitiesInformation>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <brokerOrMarketmakerDetails>
        <name>Fidelity Brokerage Services LLC</name>
        <address>
          <com:street1>900 Salem St</com:street1>
          <com:city>Smithfield</com:city>
          <com:stateOrCountry>RI</com:stateOrCountry>
          <com:zipCode>02917</com:zipCode>
        </address>
      </brokerOrMarketmakerDetails>
      <noOfUnitsSold>5000</noOfUnitsSold>
      <aggregateMarketValue>100000.00</aggregateMarketValue>
      <noOfUnitsOutstanding>69490739</noOfUnitsOutstanding>
      <approxSaleDate>07/17/2023</approxSaleDate>
      <securitiesExchangeName>NYSE</securitiesExchangeName>
    </securitiesInformation>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>07/17/2023</acquiredDate>
      <natureOfAcquisitionTransaction>Options Granted - 03/28/2018</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Issuer</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>5000</amountOfSecuritiesAcquired>
      <paymentDate>07/17/2023</paymentDate>
      <natureOfPayment>Cash</natureOfPayment>
    </securitiesToBeSold>
    <nothingToReportFlagOnSecuritiesSoldInPast3Months>N</nothingToReportFlagOnSecuritiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>John S. Peters</name>
        <address>
          <com:street1>5 Crosby Street, 3rd Floor</com:street1>
          <com:city>New York</com:city>
          <com:stateOrCountry>NY</com:stateOrCountry>
          <com:zipCode>10013</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <saleDate>06/05/2023</saleDate>
      <amountOfSecuritiesSold>538</amountOfSecuritiesSold>
      <grossProceeds>9822.54</grossProceeds>
    </securitiesSoldInPast3Months>
    <noticeSignature>
      <noticeDate>07/17/2023</noticeDate>
      <planAdoptionDates>
        <planAdoptionDate>03/17/2023</planAdoptionDate>
      </planAdoptionDates>
      <signature>/s/ Jennifer Ruchti, as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for John S. Peters</signature>
    </noticeSignature>
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144
0001816299
XXXXXXXX
LIVE
0001691421
Lemonade, Inc.
001-39367
5 CROSBY STREET
3RD FLOOR
NEW YORK
NY
10013
(844) 733-8666
Peters John Sheldon
Officer
Common
Fidelity Brokerage Services LLC
900 Salem St
Smithfield
RI
02917
5000
100000.00
69490739
07/17/2023
NYSE
Common
07/17/2023
Options Granted - 03/28/2018
Issuer
N
5000
07/17/2023
Cash
N
John S. Peters
5 Crosby Street, 3rd Floor
New York
NY
10013
Common
06/05/2023
538
9822.54
07/17/2023
03/17/2023
/s/ Jennifer Ruchti, as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for John S. Peters