<?xml version="1.0" encoding="UTF-8"?>

<!--XBRL Document Created with the Workiva Platform-->
<!--Copyright 2026 Workiva-->
<!--r:019c9bca-206f-7f31-b08f-4ade418aaac9,g:88a3e679-6145-454a-b1b1-0cf891a7d885-->
<link:linkbase xmlns:link="http://www.xbrl.org/2003/linkbase" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.xbrl.org/2003/linkbase http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd">
  <link:arcroleRef arcroleURI="https://xbrl.org/2023/arcrole/summation-item" xlink:type="simple" xlink:href="https://www.xbrl.org/2023/calculation-1.1.xsd#summation-item"/>
  <link:roleRef roleURI="http://lemonade.com/role/CONDENSEDCONSOLIDATEDBALANCESHEETS" xlink:type="simple" xlink:href="lmnd-20260331.xsd#CONDENSEDCONSOLIDATEDBALANCESHEETS"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/CONDENSEDCONSOLIDATEDBALANCESHEETS" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_019c9bca-21da-743f-99f6-826cfcfd140c" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapital_019c9bca-21da-7401-bb1f-5605f6a2d765" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AdditionalPaidInCapital"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019c9bca-21da-743f-99f6-826cfcfd140c" xlink:to="loc_us-gaap_AdditionalPaidInCapital_019c9bca-21da-7401-bb1f-5605f6a2d765" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_019c9bca-21da-7a04-b514-ef74156e1d43" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019c9bca-21da-743f-99f6-826cfcfd140c" xlink:to="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_019c9bca-21da-7a04-b514-ef74156e1d43" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValue_019c9bca-21da-7365-8622-da42f30c14ef" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommonStockValue"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019c9bca-21da-743f-99f6-826cfcfd140c" xlink:to="loc_us-gaap_CommonStockValue_019c9bca-21da-7365-8622-da42f30c14ef" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit_019c9bca-21da-726c-bce9-f2705556618c" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019c9bca-21da-743f-99f6-826cfcfd140c" xlink:to="loc_us-gaap_RetainedEarningsAccumulatedDeficit_019c9bca-21da-726c-bce9-f2705556618c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity_019c9bca-21da-7fd7-9e62-9d6b1f6e6782" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilitiesAndStockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_019c9bca-21da-7091-a037-6f58bb37d71f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Liabilities"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_019c9bca-21da-7fd7-9e62-9d6b1f6e6782" xlink:to="loc_us-gaap_Liabilities_019c9bca-21da-7091-a037-6f58bb37d71f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_019c9bca-21da-75e9-b53f-9f3d0ca61c3f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StockholdersEquity"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_019c9bca-21da-7fd7-9e62-9d6b1f6e6782" xlink:to="loc_us-gaap_StockholdersEquity_019c9bca-21da-75e9-b53f-9f3d0ca61c3f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingencies_019c9bca-21da-70a1-9762-c4a9cd1c455b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommitmentsAndContingencies"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_019c9bca-21da-7fd7-9e62-9d6b1f6e6782" xlink:to="loc_us-gaap_CommitmentsAndContingencies_019c9bca-21da-70a1-9762-c4a9cd1c455b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Investments_019c9bca-21da-7823-adf4-ca80354706cb" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Investments"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019c9bca-21da-76b6-a00c-0667c9e8ac9f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Investments_019c9bca-21da-7823-adf4-ca80354706cb" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019c9bca-21da-76b6-a00c-0667c9e8ac9f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermInvestments_019c9bca-21da-7331-a23e-a5645064f722" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShortTermInvestments"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Investments_019c9bca-21da-7823-adf4-ca80354706cb" xlink:to="loc_us-gaap_ShortTermInvestments_019c9bca-21da-7331-a23e-a5645064f722" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets_019c9bca-21da-7b58-9152-f987adaa3ee9" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Assets"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_019c9bca-21da-7853-98d0-c5424ef830fc" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019c9bca-21da-7b58-9152-f987adaa3ee9" xlink:to="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_019c9bca-21da-7853-98d0-c5424ef830fc" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAtCarryingValue_019c9bca-21da-7d74-8e43-6e4a3b4b7c41" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PremiumsReceivableAtCarryingValue"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019c9bca-21da-7b58-9152-f987adaa3ee9" xlink:to="loc_us-gaap_PremiumsReceivableAtCarryingValue_019c9bca-21da-7d74-8e43-6e4a3b4b7c41" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCosts_019c9bca-21da-71bc-9042-aacd9eff0803" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredPolicyAcquisitionCosts"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019c9bca-21da-7b58-9152-f987adaa3ee9" xlink:to="loc_us-gaap_DeferredPolicyAcquisitionCosts_019c9bca-21da-71bc-9042-aacd9eff0803" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019c9bca-21da-7238-87a1-5a6d90ea4ba8" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019c9bca-21da-7b58-9152-f987adaa3ee9" xlink:to="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019c9bca-21da-7238-87a1-5a6d90ea4ba8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssets_019c9bca-21da-7aa2-83b3-b1833dee3050" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherAssets"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019c9bca-21da-7b58-9152-f987adaa3ee9" xlink:to="loc_us-gaap_OtherAssets_019c9bca-21da-7aa2-83b3-b1833dee3050" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Goodwill_019c9bca-21da-7ce3-8212-651f35b26e9e" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Goodwill"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019c9bca-21da-7b58-9152-f987adaa3ee9" xlink:to="loc_us-gaap_Goodwill_019c9bca-21da-7ce3-8212-651f35b26e9e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill_019c9bca-21da-750c-b5cd-2abee82bc302" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IntangibleAssetsNetExcludingGoodwill"/>
    <link:calculationArc order="7" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019c9bca-21da-7b58-9152-f987adaa3ee9" xlink:to="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill_019c9bca-21da-750c-b5cd-2abee82bc302" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Investments_019c9bca-21da-7a52-ac0e-00edc34bd09b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Investments"/>
    <link:calculationArc order="8" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019c9bca-21da-7b58-9152-f987adaa3ee9" xlink:to="loc_us-gaap_Investments_019c9bca-21da-7a52-ac0e-00edc34bd09b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrepaidReinsurancePremiums_019c9bca-21da-7923-9116-470368df3c25" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PrepaidReinsurancePremiums"/>
    <link:calculationArc order="9" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019c9bca-21da-7b58-9152-f987adaa3ee9" xlink:to="loc_us-gaap_PrepaidReinsurancePremiums_019c9bca-21da-7923-9116-470368df3c25" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentNet_019c9bca-21da-7c24-9985-dad96fdb00ec" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PropertyPlantAndEquipmentNet"/>
    <link:calculationArc order="10" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019c9bca-21da-7b58-9152-f987adaa3ee9" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentNet_019c9bca-21da-7c24-9985-dad96fdb00ec" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_019c9bca-21da-7d75-a649-17c673e8aeb9" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Liabilities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019c9bca-21da-7527-a2c7-0815ec9d13d6" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019c9bca-21da-7d75-a649-17c673e8aeb9" xlink:to="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019c9bca-21da-7527-a2c7-0815ec9d13d6" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnearnedPremiums_019c9bca-21da-7a92-8898-85dafd41f482" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_UnearnedPremiums"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019c9bca-21da-7d75-a649-17c673e8aeb9" xlink:to="loc_us-gaap_UnearnedPremiums_019c9bca-21da-7a92-8898-85dafd41f482" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsPayableTradeCurrentAndNoncurrent_019c9bca-21da-74a3-9b06-5e3df19b0de0" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccountsPayableTradeCurrentAndNoncurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019c9bca-21da-7d75-a649-17c673e8aeb9" xlink:to="loc_us-gaap_AccountsPayableTradeCurrentAndNoncurrent_019c9bca-21da-74a3-9b06-5e3df19b0de0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_019c9bca-21da-71db-8ee2-2d9278282a2c" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FundsHeldUnderReinsuranceAgreementsLiability"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019c9bca-21da-7d75-a649-17c673e8aeb9" xlink:to="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_019c9bca-21da-71db-8ee2-2d9278282a2c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_DeferredCedingCommission_019c9bca-21da-7e6c-8163-9bdf51589b3d" xlink:href="lmnd-20260331.xsd#lmnd_DeferredCedingCommission"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019c9bca-21da-7d75-a649-17c673e8aeb9" xlink:to="loc_lmnd_DeferredCedingCommission_019c9bca-21da-7e6c-8163-9bdf51589b3d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsPayable_019c9bca-21da-7fc0-b866-5eaddeaa5a7d" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CededPremiumsPayable"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019c9bca-21da-7d75-a649-17c673e8aeb9" xlink:to="loc_us-gaap_CededPremiumsPayable_019c9bca-21da-7fc0-b866-5eaddeaa5a7d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCredit_019c9bca-21da-7936-a0df-76d199c0502d" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LineOfCredit"/>
    <link:calculationArc order="7" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019c9bca-21da-7d75-a649-17c673e8aeb9" xlink:to="loc_us-gaap_LineOfCredit_019c9bca-21da-7936-a0df-76d199c0502d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-7d27-93ac-e16b69ab0239" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccruedLiabilitiesAndOtherLiabilities"/>
    <link:calculationArc order="8" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019c9bca-21da-7d75-a649-17c673e8aeb9" xlink:to="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-7d27-93ac-e16b69ab0239" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVELOSS" xlink:type="simple" xlink:href="lmnd-20260331.xsd#CONDENSEDCONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVELOSS"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVELOSS" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTax_019c9bca-21da-7a18-bec1-da9b1ec1e8e8" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ComprehensiveIncomeNetOfTax"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7527-9e79-2bc4faea1c84" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetIncomeLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax_019c9bca-21da-7a18-bec1-da9b1ec1e8e8" xlink:to="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7527-9e79-2bc4faea1c84" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeAvailableforsaleSecuritiesAdjustmentNetOfTaxPortionAttributableToParent_019c9bca-21da-7c02-8c18-38e0b5a76fce" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherComprehensiveIncomeAvailableforsaleSecuritiesAdjustmentNetOfTaxPortionAttributableToParent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax_019c9bca-21da-7a18-bec1-da9b1ec1e8e8" xlink:to="loc_us-gaap_OtherComprehensiveIncomeAvailableforsaleSecuritiesAdjustmentNetOfTaxPortionAttributableToParent_019c9bca-21da-7c02-8c18-38e0b5a76fce" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeForeignCurrencyTransactionAndTranslationAdjustmentNetOfTaxPortionAttributableToParent_019c9bca-21da-7f32-8f74-0e625a8ae37d" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherComprehensiveIncomeForeignCurrencyTransactionAndTranslationAdjustmentNetOfTaxPortionAttributableToParent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax_019c9bca-21da-7a18-bec1-da9b1ec1e8e8" xlink:to="loc_us-gaap_OtherComprehensiveIncomeForeignCurrencyTransactionAndTranslationAdjustmentNetOfTaxPortionAttributableToParent_019c9bca-21da-7f32-8f74-0e625a8ae37d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7f32-9296-6269f1e0c9f5" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit_019c9bca-21da-774a-b18f-2c244fc6b5fc" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7f32-9296-6269f1e0c9f5" xlink:to="loc_us-gaap_IncomeTaxExpenseBenefit_019c9bca-21da-774a-b18f-2c244fc6b5fc" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019c9bca-21da-7f62-933d-900f84c01dd7" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7f32-9296-6269f1e0c9f5" xlink:to="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019c9bca-21da-7f62-933d-900f84c01dd7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BenefitsLossesAndExpenses_019c9bca-21da-7aa4-9bf3-d3e07bf0fa76" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BenefitsLossesAndExpenses"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019c9bca-21da-75e1-bdec-4b6ae06e2bb6" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_BenefitsLossesAndExpenses_019c9bca-21da-7aa4-9bf3-d3e07bf0fa76" xlink:to="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019c9bca-21da-75e1-bdec-4b6ae06e2bb6" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_OtherInsuranceExpense_019c9bca-21da-71f6-a1c1-e796358a5eeb" xlink:href="lmnd-20260331.xsd#lmnd_OtherInsuranceExpense"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_BenefitsLossesAndExpenses_019c9bca-21da-7aa4-9bf3-d3e07bf0fa76" xlink:to="loc_lmnd_OtherInsuranceExpense_019c9bca-21da-71f6-a1c1-e796358a5eeb" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ResearchAndDevelopmentExpense_019c9bca-21da-7956-89bd-61d0f4eb1bfb" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ResearchAndDevelopmentExpense"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_BenefitsLossesAndExpenses_019c9bca-21da-7aa4-9bf3-d3e07bf0fa76" xlink:to="loc_us-gaap_ResearchAndDevelopmentExpense_019c9bca-21da-7956-89bd-61d0f4eb1bfb" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SellingAndMarketingExpense_019c9bca-21da-732b-86f5-9513f3821ef9" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SellingAndMarketingExpense"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_BenefitsLossesAndExpenses_019c9bca-21da-7aa4-9bf3-d3e07bf0fa76" xlink:to="loc_us-gaap_SellingAndMarketingExpense_019c9bca-21da-732b-86f5-9513f3821ef9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpense_019c9bca-21da-7f74-8707-a1de84768306" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GeneralAndAdministrativeExpense"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_BenefitsLossesAndExpenses_019c9bca-21da-7aa4-9bf3-d3e07bf0fa76" xlink:to="loc_us-gaap_GeneralAndAdministrativeExpense_019c9bca-21da-7f74-8707-a1de84768306" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019c9bca-21da-73d9-9237-dac45dace3b7" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BenefitsLossesAndExpenses_019c9bca-21da-7641-9bd9-b49cb0d3792a" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BenefitsLossesAndExpenses"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019c9bca-21da-73d9-9237-dac45dace3b7" xlink:to="loc_us-gaap_BenefitsLossesAndExpenses_019c9bca-21da-7641-9bd9-b49cb0d3792a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues_019c9bca-21da-7c3c-a61d-04cb58612883" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Revenues"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019c9bca-21da-73d9-9237-dac45dace3b7" xlink:to="loc_us-gaap_Revenues_019c9bca-21da-7c3c-a61d-04cb58612883" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues_019c9bca-21da-70a1-baac-a9117c87f92c" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Revenues"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetInvestmentIncome_019c9bca-21da-7d7d-a0fd-1acf2f32df6f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetInvestmentIncome"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Revenues_019c9bca-21da-70a1-baac-a9117c87f92c" xlink:to="loc_us-gaap_NetInvestmentIncome_019c9bca-21da-7d7d-a0fd-1acf2f32df6f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_CededCommissionIncome_019c9bca-21da-701e-9a6f-f058f0c86c63" xlink:href="lmnd-20260331.xsd#lmnd_CededCommissionIncome"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Revenues_019c9bca-21da-70a1-baac-a9117c87f92c" xlink:to="loc_lmnd_CededCommissionIncome_019c9bca-21da-701e-9a6f-f058f0c86c63" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsEarnedNet_019c9bca-21da-7d4d-ace4-c40890bf60d9" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PremiumsEarnedNet"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Revenues_019c9bca-21da-70a1-baac-a9117c87f92c" xlink:to="loc_us-gaap_PremiumsEarnedNet_019c9bca-21da-7d4d-ace4-c40890bf60d9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceCommissionsAndFees_019c9bca-21da-7599-9459-4a1448f61122" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InsuranceCommissionsAndFees"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Revenues_019c9bca-21da-70a1-baac-a9117c87f92c" xlink:to="loc_us-gaap_InsuranceCommissionsAndFees_019c9bca-21da-7599-9459-4a1448f61122" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFCASHFLOWS" xlink:type="simple" xlink:href="lmnd-20260331.xsd#CONDENSEDCONSOLIDATEDSTATEMENTSOFCASHFLOWS"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFCASHFLOWS" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019c9bca-21da-7712-9639-965b95d4ce8b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-75ce-b49c-0068da932bfd" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019c9bca-21da-7712-9639-965b95d4ce8b" xlink:to="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-75ce-b49c-0068da932bfd" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019c9bca-21da-7b09-8bcd-989e2a3e6c43" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019c9bca-21da-7712-9639-965b95d4ce8b" xlink:to="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019c9bca-21da-7b09-8bcd-989e2a3e6c43" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectOfExchangeRateOnCashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019c9bca-21da-7193-a4ab-9be7e56d7ec9" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectOfExchangeRateOnCashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019c9bca-21da-7712-9639-965b95d4ce8b" xlink:to="loc_us-gaap_EffectOfExchangeRateOnCashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019c9bca-21da-7193-a4ab-9be7e56d7ec9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019c9bca-21da-73ec-85da-bfc7102d0f71" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019c9bca-21da-7712-9639-965b95d4ce8b" xlink:to="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019c9bca-21da-73ec-85da-bfc7102d0f71" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019c9bca-21da-7f59-8a5d-ee0f31890ba0" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_019c9bca-21da-7a06-93a1-5164e4b05c11" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019c9bca-21da-7f59-8a5d-ee0f31890ba0" xlink:to="loc_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_019c9bca-21da-7a06-93a1-5164e4b05c11" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleAndMaturityOfAvailableForSaleSecurities_019c9bca-21da-7175-a21e-816887f0c532" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromSaleAndMaturityOfAvailableForSaleSecurities"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019c9bca-21da-7f59-8a5d-ee0f31890ba0" xlink:to="loc_us-gaap_ProceedsFromSaleAndMaturityOfAvailableForSaleSecurities_019c9bca-21da-7175-a21e-816887f0c532" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireMarketableSecurities_019c9bca-21da-721a-8d72-2e04287dc55e" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsToAcquireMarketableSecurities"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019c9bca-21da-7f59-8a5d-ee0f31890ba0" xlink:to="loc_us-gaap_PaymentsToAcquireMarketableSecurities_019c9bca-21da-721a-8d72-2e04287dc55e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_019c9bca-21da-7e89-a24e-4b95f7e15700" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019c9bca-21da-7f59-8a5d-ee0f31890ba0" xlink:to="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_019c9bca-21da-7e89-a24e-4b95f7e15700" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_019c9bca-21da-7a0e-871e-644df2ecb6d2" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsToAcquirePropertyPlantAndEquipment"/>
    <link:calculationArc order="5" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019c9bca-21da-7f59-8a5d-ee0f31890ba0" xlink:to="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_019c9bca-21da-7a0e-871e-644df2ecb6d2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7f75-8565-bda149f62c44" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetIncomeLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7f75-8565-bda149f62c44" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepreciationDepletionAndAmortization_019c9bca-21da-7595-af26-792f5db931a8" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DepreciationDepletionAndAmortization"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_DepreciationDepletionAndAmortization_019c9bca-21da-7595-af26-792f5db931a8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensation_019c9bca-21da-7ca3-b2b7-750ba11e0eed" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensation"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_ShareBasedCompensation_019c9bca-21da-7ca3-b2b7-750ba11e0eed" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccretionAmortizationOfDiscountsAndPremiumsInvestments_019c9bca-21da-7322-aa4d-b46d9217749f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccretionAmortizationOfDiscountsAndPremiumsInvestments"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_AccretionAmortizationOfDiscountsAndPremiumsInvestments_019c9bca-21da-7322-aa4d-b46d9217749f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProvisionForDoubtfulAccounts_019c9bca-21da-70dd-bf2a-656fbcbd84c9" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProvisionForDoubtfulAccounts"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_ProvisionForDoubtfulAccounts_019c9bca-21da-70dd-bf2a-656fbcbd84c9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPremiumsReceivable_019c9bca-21da-73be-a268-2eedcfcc9996" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInPremiumsReceivable"/>
    <link:calculationArc order="6" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_IncreaseDecreaseInPremiumsReceivable_019c9bca-21da-73be-a268-2eedcfcc9996" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_019c9bca-21da-7fe3-87d9-9248407bc75f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInReinsuranceRecoverable"/>
    <link:calculationArc order="7" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_019c9bca-21da-7fe3-87d9-9248407bc75f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums_019c9bca-21da-7a93-9b24-7ce26f35cc0d" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums"/>
    <link:calculationArc order="8" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums_019c9bca-21da-7a93-9b24-7ce26f35cc0d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_019c9bca-21da-70c5-94e0-6ba9c7725fa0" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts"/>
    <link:calculationArc order="9" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_019c9bca-21da-70c5-94e0-6ba9c7725fa0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets_019c9bca-21da-7cdc-979a-baf5baab51e9" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInOtherOperatingAssets"/>
    <link:calculationArc order="10" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets_019c9bca-21da-7cdc-979a-baf5baab51e9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_019c9bca-21da-7059-8316-84a2ba4f946d" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve"/>
    <link:calculationArc order="11" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_019c9bca-21da-7059-8316-84a2ba4f946d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInUnearnedPremiumsNet_019c9bca-21da-7f7c-a201-39a0af53873a" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInUnearnedPremiumsNet"/>
    <link:calculationArc order="12" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_IncreaseDecreaseInUnearnedPremiumsNet_019c9bca-21da-7f7c-a201-39a0af53873a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsPayable_019c9bca-21da-7b9c-a388-295109fdc4be" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInAccountsPayable"/>
    <link:calculationArc order="13" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_IncreaseDecreaseInAccountsPayable_019c9bca-21da-7b9c-a388-295109fdc4be" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsurancePayables_019c9bca-21da-7851-8c1b-6d51b611b018" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInReinsurancePayables"/>
    <link:calculationArc order="14" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_IncreaseDecreaseInReinsurancePayables_019c9bca-21da-7851-8c1b-6d51b611b018" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_IncreaseDecreaseInDeferredCedingCommissions_019c9bca-21da-713b-aa91-5fbd25043bf9" xlink:href="lmnd-20260331.xsd#lmnd_IncreaseDecreaseInDeferredCedingCommissions"/>
    <link:calculationArc order="15" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_lmnd_IncreaseDecreaseInDeferredCedingCommissions_019c9bca-21da-713b-aa91-5fbd25043bf9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_IncreaseDecreaseInCededPremiumsPayable_019c9bca-21da-71d4-948b-609fe61f9555" xlink:href="lmnd-20260331.xsd#lmnd_IncreaseDecreaseInCededPremiumsPayable"/>
    <link:calculationArc order="16" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_lmnd_IncreaseDecreaseInCededPremiumsPayable_019c9bca-21da-71d4-948b-609fe61f9555" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccruedLiabilitiesAndOtherOperatingLiabilities_019c9bca-21da-7ca1-9c76-5f0a9865ae8b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInAccruedLiabilitiesAndOtherOperatingLiabilities"/>
    <link:calculationArc order="17" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019c9bca-21da-7f40-928f-62b9962f73bc" xlink:to="loc_us-gaap_IncreaseDecreaseInAccruedLiabilitiesAndOtherOperatingLiabilities_019c9bca-21da-7ca1-9c76-5f0a9865ae8b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019c9bca-21da-7bb2-bb10-cf1dc10cb62b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromLinesOfCredit_019c9bca-21da-7dd4-b8e7-c8c2ae8d8d76" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromLinesOfCredit"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019c9bca-21da-7bb2-bb10-cf1dc10cb62b" xlink:to="loc_us-gaap_ProceedsFromLinesOfCredit_019c9bca-21da-7dd4-b8e7-c8c2ae8d8d76" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfLinesOfCredit_019c9bca-21da-7442-a9ea-30830a91f837" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RepaymentsOfLinesOfCredit"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019c9bca-21da-7bb2-bb10-cf1dc10cb62b" xlink:to="loc_us-gaap_RepaymentsOfLinesOfCredit_019c9bca-21da-7442-a9ea-30830a91f837" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromStockOptionsExercised_019c9bca-21da-7bfd-a548-44a4222e77f2" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromStockOptionsExercised"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019c9bca-21da-7bb2-bb10-cf1dc10cb62b" xlink:to="loc_us-gaap_ProceedsFromStockOptionsExercised_019c9bca-21da-7bfd-a548-44a4222e77f2" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/SummaryofSignificantAccountingPoliciesCashCashEquivalentsandRestrictedCashDetails" xlink:type="simple" xlink:href="lmnd-20260331.xsd#SummaryofSignificantAccountingPoliciesCashCashEquivalentsandRestrictedCashDetails"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/SummaryofSignificantAccountingPoliciesCashCashEquivalentsandRestrictedCashDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019c9bca-21da-74c1-80a8-078fd949d4c6" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_019c9bca-21da-7f23-b46e-2cb4f4e86b62" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019c9bca-21da-74c1-80a8-078fd949d4c6" xlink:to="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_019c9bca-21da-7f23-b46e-2cb4f4e86b62" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCash_019c9bca-21da-79b5-bf93-10ac6682664c" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RestrictedCash"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019c9bca-21da-74c1-80a8-078fd949d4c6" xlink:to="loc_us-gaap_RestrictedCash_019c9bca-21da-79b5-bf93-10ac6682664c" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/InvestmentsAmortizedCostandFairValuesofInvestmentinFixedMaturitiesDetails" xlink:type="simple" xlink:href="lmnd-20260331.xsd#InvestmentsAmortizedCostandFairValuesofInvestmentinFixedMaturitiesDetails"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/InvestmentsAmortizedCostandFairValuesofInvestmentinFixedMaturitiesDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019c9bca-21da-7c0f-91d0-bf7f4d541780" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_019c9bca-21da-7866-8cff-59278ce01097" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019c9bca-21da-7c0f-91d0-bf7f4d541780" xlink:to="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_019c9bca-21da-7866-8cff-59278ce01097" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_019c9bca-21da-74af-a320-96ee2135d061" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019c9bca-21da-7c0f-91d0-bf7f4d541780" xlink:to="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_019c9bca-21da-74af-a320-96ee2135d061" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019c9bca-21da-765b-b5eb-4865fb9d9c2f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019c9bca-21da-7c0f-91d0-bf7f4d541780" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019c9bca-21da-765b-b5eb-4865fb9d9c2f" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/InvestmentsContractualMaturitiesofBondsDetails" xlink:type="simple" xlink:href="lmnd-20260331.xsd#InvestmentsContractualMaturitiesofBondsDetails"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/InvestmentsContractualMaturitiesofBondsDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019c9bca-21da-752b-818b-8d0419c5c847" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearSixThroughTenAmortizedCostBasis_019c9bca-21da-76d4-8883-95a7acc5dbb5" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearSixThroughTenAmortizedCostBasis"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019c9bca-21da-752b-818b-8d0419c5c847" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearSixThroughTenAmortizedCostBasis_019c9bca-21da-76d4-8883-95a7acc5dbb5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearTwoThroughFiveAmortizedCostBasis_019c9bca-21da-7f36-b5f6-85c1d862f16f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearTwoThroughFiveAmortizedCostBasis"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019c9bca-21da-752b-818b-8d0419c5c847" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearTwoThroughFiveAmortizedCostBasis_019c9bca-21da-7f36-b5f6-85c1d862f16f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingAfterYearTenAmortizedCostBasis_019c9bca-21da-7d0c-aabd-3c22e2e30f79" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingAfterYearTenAmortizedCostBasis"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019c9bca-21da-752b-818b-8d0419c5c847" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingAfterYearTenAmortizedCostBasis_019c9bca-21da-7d0c-aabd-3c22e2e30f79" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesNextRollingTwelveMonthsAmortizedCostBasis_019c9bca-21da-773c-a2e5-996a3d0b3797" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesNextRollingTwelveMonthsAmortizedCostBasis"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019c9bca-21da-752b-818b-8d0419c5c847" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesNextRollingTwelveMonthsAmortizedCostBasis_019c9bca-21da-773c-a2e5-996a3d0b3797" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019c9bca-21da-765a-b31b-152c47509827" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearTwoThroughFiveFairValue_019c9bca-21da-77d7-9e42-c3c594383dac" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearTwoThroughFiveFairValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019c9bca-21da-765a-b31b-152c47509827" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearTwoThroughFiveFairValue_019c9bca-21da-77d7-9e42-c3c594383dac" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearSixThroughTenFairValue_019c9bca-21da-71ad-a07a-6628ac78fed8" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearSixThroughTenFairValue"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019c9bca-21da-765a-b31b-152c47509827" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearSixThroughTenFairValue_019c9bca-21da-71ad-a07a-6628ac78fed8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingAfterYearTenFairValue_019c9bca-21da-7858-b7e1-d064bba5e569" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingAfterYearTenFairValue"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019c9bca-21da-765a-b31b-152c47509827" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingAfterYearTenFairValue_019c9bca-21da-7858-b7e1-d064bba5e569" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesNextRollingTwelveMonthsFairValue_019c9bca-21da-7282-9db7-ac4c054a34db" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesNextRollingTwelveMonthsFairValue"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019c9bca-21da-765a-b31b-152c47509827" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesNextRollingTwelveMonthsFairValue_019c9bca-21da-7282-9db7-ac4c054a34db" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/InvestmentsAgingofGrossUnrealizedLossesDetails" xlink:type="simple" xlink:href="lmnd-20260331.xsd#InvestmentsAgingofGrossUnrealizedLossesDetails"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/InvestmentsAgingofGrossUnrealizedLossesDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_019c9bca-21da-7d80-8933-4c74bbf69c67" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_019c9bca-21da-729f-8a57-9080568fa363" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_019c9bca-21da-7d80-8933-4c74bbf69c67" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_019c9bca-21da-729f-8a57-9080568fa363" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_019c9bca-21da-7547-b4d3-ba78a743415b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_019c9bca-21da-7d80-8933-4c74bbf69c67" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_019c9bca-21da-7547-b4d3-ba78a743415b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_019c9bca-21da-7b22-b760-c4d4f8fd6654" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_019c9bca-21da-7413-a6fa-d358918026c5" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_019c9bca-21da-7b22-b760-c4d4f8fd6654" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_019c9bca-21da-7413-a6fa-d358918026c5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019c9bca-21da-7bf2-af29-6541764d601f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_019c9bca-21da-7b22-b760-c4d4f8fd6654" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019c9bca-21da-7bf2-af29-6541764d601f" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/FairValueMeasurementsFairValueHierarchyforFinancialAssetsandLiabilitiesDetails" xlink:type="simple" xlink:href="lmnd-20260331.xsd#FairValueMeasurementsFairValueHierarchyforFinancialAssetsandLiabilitiesDetails"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/FairValueMeasurementsFairValueHierarchyforFinancialAssetsandLiabilitiesDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsFairValueDisclosure_019c9bca-21da-7e96-9bca-c55417e032e1" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AssetsFairValueDisclosure"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermInvestments_019c9bca-21da-7245-ad19-5d6b5a59bab8" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShortTermInvestments"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsFairValueDisclosure_019c9bca-21da-7e96-9bca-c55417e032e1" xlink:to="loc_us-gaap_ShortTermInvestments_019c9bca-21da-7245-ad19-5d6b5a59bab8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019c9bca-21da-7efb-a946-72ff1d735c4c" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsFairValueDisclosure_019c9bca-21da-7e96-9bca-c55417e032e1" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019c9bca-21da-7efb-a946-72ff1d735c4c" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/UnpaidLossandLossAdjustmentExpenseActivityintheLiabilityforUnpaidLossandLAEDetails" xlink:type="simple" xlink:href="lmnd-20260331.xsd#UnpaidLossandLossAdjustmentExpenseActivityintheLiabilityforUnpaidLossandLAEDetails"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/UnpaidLossandLossAdjustmentExpenseActivityintheLiabilityforUnpaidLossandLAEDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_019c9bca-21da-7610-99f3-1d061588ca7a" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsForLossesAndLossAdjustmentExpense"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_019c9bca-21da-7f79-bb38-a4ed25e8d723" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_019c9bca-21da-7610-99f3-1d061588ca7a" xlink:to="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_019c9bca-21da-7f79-bb38-a4ed25e8d723" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_019c9bca-21da-796b-9dcc-f1b881b13130" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_019c9bca-21da-7610-99f3-1d061588ca7a" xlink:to="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_019c9bca-21da-796b-9dcc-f1b881b13130" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019c9bca-21da-7b2a-8284-475b26a211cf" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019c9bca-21da-7685-8c57-8636ea262055" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019c9bca-21da-7b2a-8284-475b26a211cf" xlink:to="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019c9bca-21da-7685-8c57-8636ea262055" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019c9bca-21da-7688-8404-b644a5e2c142" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019c9bca-21da-7b2a-8284-475b26a211cf" xlink:to="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019c9bca-21da-7688-8404-b644a5e2c142" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019c9bca-21da-7441-a79c-eb2577e01aad" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_019c9bca-21da-7dc4-b17d-0633fa5b98a8" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019c9bca-21da-7441-a79c-eb2577e01aad" xlink:to="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_019c9bca-21da-7dc4-b17d-0633fa5b98a8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_019c9bca-21da-7e58-bd0c-946303c19a94" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019c9bca-21da-7441-a79c-eb2577e01aad" xlink:to="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_019c9bca-21da-7e58-bd0c-946303c19a94" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/OtherLiabilitiesandAccruedExpensesDetails" xlink:type="simple" xlink:href="lmnd-20260331.xsd#OtherLiabilitiesandAccruedExpensesDetails"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/OtherLiabilitiesandAccruedExpensesDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccruedLiabilitiesAndOtherLiabilities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedAdvertisingCurrentAndNoncurrent_019c9bca-21da-7296-bbbd-66f412f1b06a" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccruedAdvertisingCurrentAndNoncurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:to="loc_us-gaap_AccruedAdvertisingCurrentAndNoncurrent_019c9bca-21da-7296-bbbd-66f412f1b06a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_UncertainTaxPosition_019c9bca-21da-7d31-b929-dabc811f99e5" xlink:href="lmnd-20260331.xsd#lmnd_UncertainTaxPosition"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:to="loc_lmnd_UncertainTaxPosition_019c9bca-21da-7d31-b929-dabc811f99e5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeRelatedLiabilitiesCurrentAndNoncurrent_019c9bca-21da-7915-9d6e-f496eaebabe2" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EmployeeRelatedLiabilitiesCurrentAndNoncurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:to="loc_us-gaap_EmployeeRelatedLiabilitiesCurrentAndNoncurrent_019c9bca-21da-7915-9d6e-f496eaebabe2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiability_019c9bca-21da-7489-9100-1dbdef87407b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OperatingLeaseLiability"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:to="loc_us-gaap_OperatingLeaseLiability_019c9bca-21da-7489-9100-1dbdef87407b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_PayableToCarriers_019c9bca-21da-7edd-8f1e-499a0d235ece" xlink:href="lmnd-20260331.xsd#lmnd_PayableToCarriers"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:to="loc_lmnd_PayableToCarriers_019c9bca-21da-7edd-8f1e-499a0d235ece" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_AdvancePremiumLiability_019c9bca-21da-73c7-af39-79947fae3715" xlink:href="lmnd-20260331.xsd#lmnd_AdvancePremiumLiability"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:to="loc_lmnd_AdvancePremiumLiability_019c9bca-21da-73c7-af39-79947fae3715" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedProfessionalFeesCurrentAndNoncurrent_019c9bca-21da-767d-a4d4-2e54977278c6" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccruedProfessionalFeesCurrentAndNoncurrent"/>
    <link:calculationArc order="7" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:to="loc_us-gaap_AccruedProfessionalFeesCurrentAndNoncurrent_019c9bca-21da-767d-a4d4-2e54977278c6" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_PremiumTaxesPayable_019c9bca-21da-7e9b-822a-a6facedbd5e8" xlink:href="lmnd-20260331.xsd#lmnd_PremiumTaxesPayable"/>
    <link:calculationArc order="8" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:to="loc_lmnd_PremiumTaxesPayable_019c9bca-21da-7e9b-822a-a6facedbd5e8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_AccruedCededCommissions_019c9bca-21da-7e91-a78f-4c7beb00554f" xlink:href="lmnd-20260331.xsd#lmnd_AccruedCededCommissions"/>
    <link:calculationArc order="9" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:to="loc_lmnd_AccruedCededCommissions_019c9bca-21da-7e91-a78f-4c7beb00554f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePayable_019c9bca-21da-7932-a29d-abf8e521a03b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReinsurancePayable"/>
    <link:calculationArc order="10" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:to="loc_us-gaap_ReinsurancePayable_019c9bca-21da-7932-a29d-abf8e521a03b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestPayableCurrentAndNoncurrent_019c9bca-21da-7d67-9344-86f608d6f664" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InterestPayableCurrentAndNoncurrent"/>
    <link:calculationArc order="11" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:to="loc_us-gaap_InterestPayableCurrentAndNoncurrent_019c9bca-21da-7d67-9344-86f608d6f664" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherSundryLiabilities_019c9bca-21da-74d2-95cb-27ffdbdd8ad9" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherSundryLiabilities"/>
    <link:calculationArc order="12" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:to="loc_us-gaap_OtherSundryLiabilities_019c9bca-21da-74d2-95cb-27ffdbdd8ad9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedIncomeTaxes_019d045a-7b7c-720e-80b5-20acb067fa89" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccruedIncomeTaxes"/>
    <link:calculationArc order="13" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019c9bca-21da-77fc-a9c8-bc31ec234ac6" xlink:to="loc_us-gaap_AccruedIncomeTaxes_019d045a-7b7c-720e-80b5-20acb067fa89" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/SegmentInformationScheduleofSegmentReportingInformationbySegmentDetails" xlink:type="simple" xlink:href="lmnd-20260331.xsd#SegmentInformationScheduleofSegmentReportingInformationbySegmentDetails"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/SegmentInformationScheduleofSegmentReportingInformationbySegmentDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7cb5-b88f-19e31a36f03a" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues_019c9bca-21da-7753-9528-40b9ab80178d" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Revenues"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7cb5-b88f-19e31a36f03a" xlink:to="loc_us-gaap_Revenues_019c9bca-21da-7753-9528-40b9ab80178d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019c9bca-21da-77e8-8798-83a2a3130eeb" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7cb5-b88f-19e31a36f03a" xlink:to="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019c9bca-21da-77e8-8798-83a2a3130eeb" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_OtherInsuranceExpense_019c9bca-21da-7717-875d-2104097b5cb4" xlink:href="lmnd-20260331.xsd#lmnd_OtherInsuranceExpense"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7cb5-b88f-19e31a36f03a" xlink:to="loc_lmnd_OtherInsuranceExpense_019c9bca-21da-7717-875d-2104097b5cb4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SellingAndMarketingExpense_019c9bca-21da-785c-963b-d44abcf51a7d" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SellingAndMarketingExpense"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7cb5-b88f-19e31a36f03a" xlink:to="loc_us-gaap_SellingAndMarketingExpense_019c9bca-21da-785c-963b-d44abcf51a7d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdvertisingExpense_019c9bca-21da-73ae-bcbc-fef49cf020bf" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AdvertisingExpense"/>
    <link:calculationArc order="5" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7cb5-b88f-19e31a36f03a" xlink:to="loc_us-gaap_AdvertisingExpense_019c9bca-21da-73ae-bcbc-fef49cf020bf" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ResearchAndDevelopmentExpense_019c9bca-21da-76b6-90ed-21a9f74cffdd" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ResearchAndDevelopmentExpense"/>
    <link:calculationArc order="6" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7cb5-b88f-19e31a36f03a" xlink:to="loc_us-gaap_ResearchAndDevelopmentExpense_019c9bca-21da-76b6-90ed-21a9f74cffdd" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_GeneralAndAdministrativeLessInterestDepreciationAndOtherSegmentIncomeExpenses_019c9bca-21da-7b89-afc3-a49568fcf14d" xlink:href="lmnd-20260331.xsd#lmnd_GeneralAndAdministrativeLessInterestDepreciationAndOtherSegmentIncomeExpenses"/>
    <link:calculationArc order="7" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7cb5-b88f-19e31a36f03a" xlink:to="loc_lmnd_GeneralAndAdministrativeLessInterestDepreciationAndOtherSegmentIncomeExpenses_019c9bca-21da-7b89-afc3-a49568fcf14d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpenseNonoperating_019c9bca-21da-77aa-a24e-d67479078927" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InterestExpenseNonoperating"/>
    <link:calculationArc order="8" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7cb5-b88f-19e31a36f03a" xlink:to="loc_us-gaap_InterestExpenseNonoperating_019c9bca-21da-77aa-a24e-d67479078927" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostOfGoodsAndServicesSoldDepreciationAndAmortization_019c9bca-21da-7373-bc07-010efd500796" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CostOfGoodsAndServicesSoldDepreciationAndAmortization"/>
    <link:calculationArc order="9" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7cb5-b88f-19e31a36f03a" xlink:to="loc_us-gaap_CostOfGoodsAndServicesSoldDepreciationAndAmortization_019c9bca-21da-7373-bc07-010efd500796" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingOtherItemAmount_019c9bca-21da-7e68-8538-16fff5931b0d" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SegmentReportingOtherItemAmount"/>
    <link:calculationArc order="10" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7cb5-b88f-19e31a36f03a" xlink:to="loc_us-gaap_SegmentReportingOtherItemAmount_019c9bca-21da-7e68-8538-16fff5931b0d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit_019c9bca-21da-79e2-8953-9866bb0bc825" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:calculationArc order="11" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019c9bca-21da-7cb5-b88f-19e31a36f03a" xlink:to="loc_us-gaap_IncomeTaxExpenseBenefit_019c9bca-21da-79e2-8953-9866bb0bc825" xlink:type="arc"/>
  </link:calculationLink>
</link:linkbase>