<SEC-DOCUMENT>0001976408-25-000257.txt : 20250814
<SEC-HEADER>0001976408-25-000257.hdr.sgml : 20250814
<ACCEPTANCE-DATETIME>20250814064443
ACCESSION NUMBER:		0001976408-25-000257
CONFORMED SUBMISSION TYPE:	144
PUBLIC DOCUMENT COUNT:		1
FILED AS OF DATE:		20250814
DATE AS OF CHANGE:		20250814

SUBJECT COMPANY:	

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			Lemonade, Inc.
		CENTRAL INDEX KEY:			0001691421
		STANDARD INDUSTRIAL CLASSIFICATION:	FIRE, MARINE & CASUALTY INSURANCE [6331]
		ORGANIZATION NAME:           	02 Finance
		EIN:				320469673
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	FILING VALUES:
		FORM TYPE:		144
		SEC ACT:		1933 Act
		SEC FILE NUMBER:	001-39367
		FILM NUMBER:		251214180

	BUSINESS ADDRESS:	
		STREET 1:		5 CROSBY STREET
		STREET 2:		3RD FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10013
		BUSINESS PHONE:		(844) 733-8666

	MAIL ADDRESS:	
		STREET 1:		5 CROSBY STREET
		STREET 2:		3RD FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10013

REPORTING-OWNER:	

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			Eckstein Adina
		CENTRAL INDEX KEY:			0001874702
		ORGANIZATION NAME:           	

	FILING VALUES:
		FORM TYPE:		144

	MAIL ADDRESS:	
		STREET 1:		C/O LEMONADE, INC.
		STREET 2:		5 CROSBY STREET, 3RD FLOOR
		CITY:			NEW YORK
		STATE:			NY
		ZIP:			10013
</SEC-HEADER>
<DOCUMENT>
<TYPE>144
<SEQUENCE>1
<FILENAME>primary_doc.xml
<TEXT>
<XML>
<?xml version="1.0" encoding="UTF-8"?><edgarSubmission xmlns="http://www.sec.gov/edgar/ownership" xmlns:com="http://www.sec.gov/edgar/common">
  <headerData>
    <submissionType>144</submissionType>
    <filerInfo>
      <filer>
        <filerCredentials>
          <cik>0001874702</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>Eckstein Adina</nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>
      <relationshipsToIssuer>
        <relationshipToIssuer>Officer</relationshipToIssuer>
      </relationshipsToIssuer>
    </issuerInfo>
    <securitiesInformation>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <brokerOrMarketmakerDetails>
        <name>Oppenheimer &amp; Co. Inc.</name>
        <address>
          <com:street1>85 Broad St.</com:street1>
          <com:city>New York</com:city>
          <com:stateOrCountry>NY</com:stateOrCountry>
          <com:zipCode>10004</com:zipCode>
        </address>
      </brokerOrMarketmakerDetails>
      <noOfUnitsSold>5000</noOfUnitsSold>
      <aggregateMarketValue>272950.00</aggregateMarketValue>
      <noOfUnitsOutstanding>73886417</noOfUnitsOutstanding>
      <approxSaleDate>08/13/2025</approxSaleDate>
      <securitiesExchangeName>NYSE</securitiesExchangeName>
    </securitiesInformation>
    <securitiesToBeSold>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <acquiredDate>06/07/2020</acquiredDate>
      <natureOfAcquisitionTransaction>Employee Stock Option Plan	</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Issuer</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>5000</amountOfSecuritiesAcquired>
      <paymentDate>08/13/2025</paymentDate>
      <natureOfPayment>Cash - Upon exercise</natureOfPayment>
    </securitiesToBeSold>
    <nothingToReportFlagOnSecuritiesSoldInPast3Months>N</nothingToReportFlagOnSecuritiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Eckstein Adina</name>
        <address>
          <com:street1>5 CROSBY STREET</com:street1>
          <com:city>New York   </com:city>
          <com:stateOrCountry>NY</com:stateOrCountry>
          <com:zipCode>10013</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <saleDate>06/23/2025</saleDate>
      <amountOfSecuritiesSold>5000</amountOfSecuritiesSold>
      <grossProceeds>225000.00</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Eckstein Adina</name>
        <address>
          <com:street1>5 CROSBY STREET</com:street1>
          <com:city>New York</com:city>
          <com:stateOrCountry>NY</com:stateOrCountry>
          <com:zipCode>10013</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common</securitiesClassTitle>
      <saleDate>08/05/2025</saleDate>
      <amountOfSecuritiesSold>5000</amountOfSecuritiesSold>
      <grossProceeds>245000.00</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Eckstein Adina</name>
        <address>
          <com:street1>5 CROSBY STREET</com:street1>
          <com:city>New York</com:city>
          <com:stateOrCountry>NY</com:stateOrCountry>
          <com:zipCode>10013</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common	</securitiesClassTitle>
      <saleDate>08/11/2025</saleDate>
      <amountOfSecuritiesSold>5000</amountOfSecuritiesSold>
      <grossProceeds>265000.00</grossProceeds>
    </securitiesSoldInPast3Months>
    <remarks>Under a 10b5-1 sale plan adopted on 12/09/2024
</remarks>
    <noticeSignature>
      <noticeDate>08/13/2025</noticeDate>
      <planAdoptionDates>
        <planAdoptionDate>12/09/2024</planAdoptionDate>
      </planAdoptionDates>
      <signature>Eckstein Adina</signature>
    </noticeSignature>
  </formData>
</edgarSubmission>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
