content: <?xml version="1.0" encoding="UTF-8"?><edgarSubmission xmlns="http://www.sec.gov/edgar/ownership" xmlns:com="http://www.sec.gov/edgar/common">
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      <submissionType>144</submissionType>
      <filerInfo>
        <filer>
          <filerCredentials>
            <cik>0001232142</cik>
            <ccc>XXXXXXXX</ccc>
          </filerCredentials>
        </filer>
        <liveTestFlag>LIVE</liveTestFlag>
  
  
  
      </filerInfo>
    </headerData>
    <formData>
      <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>BIXBY TIMOTHY E</nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>
        <relationshipsToIssuer>
          <relationshipToIssuer>Officer</relationshipToIssuer>
        </relationshipsToIssuer>
      </issuerInfo>
      <securitiesInformation>
        <securitiesClassTitle>Common</securitiesClassTitle>
        <brokerOrMarketmakerDetails>
          <name>Fidelity Brokerage Services LLC</name>
          <address>
            <com:street1>900 Salem Street</com:street1>
            <com:city>Smithfield</com:city>
            <com:stateOrCountry>RI</com:stateOrCountry>
            <com:zipCode>02917</com:zipCode>
          </address>
        </brokerOrMarketmakerDetails>
        <noOfUnitsSold>6000</noOfUnitsSold>
        <aggregateMarketValue>255000.00</aggregateMarketValue>
        <noOfUnitsOutstanding>73266170</noOfUnitsOutstanding>
        <approxSaleDate>06/16/2025</approxSaleDate>
        <securitiesExchangeName>NYSE</securitiesExchangeName>
      </securitiesInformation>
      <securitiesToBeSold>
        <securitiesClassTitle>Common</securitiesClassTitle>
        <acquiredDate>06/16/2025</acquiredDate>
        <natureOfAcquisitionTransaction>Option Granted - 12/01/2019</natureOfAcquisitionTransaction>
        <nameOfPersonfromWhomAcquired>Issuer</nameOfPersonfromWhomAcquired>
        <isGiftTransaction>N</isGiftTransaction>
        <amountOfSecuritiesAcquired>6000</amountOfSecuritiesAcquired>
        <paymentDate>06/16/2025</paymentDate>
        <natureOfPayment>Cash</natureOfPayment>
      </securitiesToBeSold>
      <nothingToReportFlagOnSecuritiesSoldInPast3Months>N</nothingToReportFlagOnSecuritiesSoldInPast3Months>
      <securitiesSoldInPast3Months>
        <sellerDetails>
          <name>Timothy E. Bixby</name>
          <address>
            <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>
          </address>
        </sellerDetails>
        <securitiesClassTitle>Common</securitiesClassTitle>
        <saleDate>03/24/2025</saleDate>
        <amountOfSecuritiesSold>5000</amountOfSecuritiesSold>
        <grossProceeds>187500.00</grossProceeds>
      </securitiesSoldInPast3Months>
      <securitiesSoldInPast3Months>
        <sellerDetails>
          <name>Timothy E. Bixby</name>
          <address>
            <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>
          </address>
        </sellerDetails>
        <securitiesClassTitle>Common</securitiesClassTitle>
        <saleDate>06/03/2025</saleDate>
        <amountOfSecuritiesSold>1916</amountOfSecuritiesSold>
        <grossProceeds>67540.92</grossProceeds>
      </securitiesSoldInPast3Months>
      <securitiesSoldInPast3Months>
        <sellerDetails>
          <name>Timothy E. Bixby</name>
          <address>
            <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>
          </address>
        </sellerDetails>
        <securitiesClassTitle>Common</securitiesClassTitle>
        <saleDate>06/05/2025</saleDate>
        <amountOfSecuritiesSold>5000</amountOfSecuritiesSold>
        <grossProceeds>187500.00</grossProceeds>
      </securitiesSoldInPast3Months>
      <securitiesSoldInPast3Months>
        <sellerDetails>
          <name>Timothy E. Bixby</name>
          <address>
            <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>
          </address>
        </sellerDetails>
        <securitiesClassTitle>Common</securitiesClassTitle>
        <saleDate>06/09/2025</saleDate>
        <amountOfSecuritiesSold>5000</amountOfSecuritiesSold>
        <grossProceeds>201500.00</grossProceeds>
      </securitiesSoldInPast3Months>
      <securitiesSoldInPast3Months>
        <sellerDetails>
          <name>Timothy E. Bixby</name>
          <address>
            <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>
          </address>
        </sellerDetails>
        <securitiesClassTitle>Common</securitiesClassTitle>
        <saleDate>06/11/2025</saleDate>
        <amountOfSecuritiesSold>6000</amountOfSecuritiesSold>
        <grossProceeds>255000.00</grossProceeds>
      </securitiesSoldInPast3Months>
      <noticeSignature>
        <noticeDate>06/16/2025</noticeDate>
        <planAdoptionDates>
          <planAdoptionDate>12/12/2024</planAdoptionDate>
        </planAdoptionDates>
        <signature>/s/ Gary Redman, as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for Timothy E. Bixby</signature>
      </noticeSignature>
    </formData>
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metadata_documents: [{"type": "144", "sequence": "1", "filename": "primary_doc.xml", "secsgml_size_bytes": 6116}]
text: 144
  0001232142
  XXXXXXXX
  LIVE
  0001691421
  Lemonade, Inc.
  001-39367
  5 CROSBY STREET
  3RD FLOOR
  NEW YORK
  NY
  10013
  (844) 733-8666
  BIXBY TIMOTHY E
  Officer
  Common
  Fidelity Brokerage Services LLC
  900 Salem Street
  Smithfield
  RI
  02917
  6000
  255000.00
  73266170
  06/16/2025
  NYSE
  Common
  06/16/2025
  Option Granted - 12/01/2019
  Issuer
  N
  6000
  06/16/2025
  Cash
  N
  Timothy E. Bixby
  5 Crosby Street
  3rd Floor
  New York
  NY
  10013
  Common
  03/24/2025
  5000
  187500.00
  Timothy E. Bixby
  5 Crosby Street
  3rd Floor
  New York
  NY
  10013
  Common
  06/03/2025
  1916
  67540.92
  Timothy E. Bixby
  5 Crosby Street
  3rd Floor
  New York
  NY
  10013
  Common
  06/05/2025
  5000
  187500.00
  Timothy E. Bixby
  5 Crosby Street
  3rd Floor
  New York
  NY
  10013
  Common
  06/09/2025
  5000
  201500.00
  Timothy E. Bixby
  5 Crosby Street
  3rd Floor
  New York
  NY
  10013
  Common
  06/11/2025
  6000
  255000.00
  06/16/2025
  12/12/2024
  /s/ Gary Redman, as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for Timothy E. Bixby