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

<!--XBRL Document Created with the Workiva Platform-->
<!--Copyright 2026 Workiva-->
<!--r:019fcdef-56b3-7872-8c9a-e5dd11ff4734,g:d20053c7-4dd3-4f66-bcd5-f5c944c1253b-->
<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-20260930.xsd#CONDENSEDCONSOLIDATEDBALANCESHEETS"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/CONDENSEDCONSOLIDATEDBALANCESHEETS" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity_019fcdef-57dd-7214-9155-8607e7d26b82" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesAndStockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_019fcdef-57dd-791b-9974-4d9af224608f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7214-9155-8607e7d26b82" xlink:to="loc_us-gaap_Liabilities_019fcdef-57dd-791b-9974-4d9af224608f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_019fcdef-57dd-771e-b5ab-0836850e6d1e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7214-9155-8607e7d26b82" xlink:to="loc_us-gaap_StockholdersEquity_019fcdef-57dd-771e-b5ab-0836850e6d1e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingencies_019fcdef-57dd-7714-a317-34c2ad7c7dac" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7214-9155-8607e7d26b82" xlink:to="loc_us-gaap_CommitmentsAndContingencies_019fcdef-57dd-7714-a317-34c2ad7c7dac" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets_019fcdef-57dd-74dc-8e0f-9ba109b23386" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Assets"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_019fcdef-57dd-7c90-80d3-16b99e1955a9" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74dc-8e0f-9ba109b23386" xlink:to="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_019fcdef-57dd-7c90-80d3-16b99e1955a9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAtCarryingValue_019fcdef-57dd-71fd-8df2-a49897939d17" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74dc-8e0f-9ba109b23386" xlink:to="loc_us-gaap_PremiumsReceivableAtCarryingValue_019fcdef-57dd-71fd-8df2-a49897939d17" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCosts_019fcdef-57dd-7d8e-9ebc-cf27abcc85b2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74dc-8e0f-9ba109b23386" xlink:to="loc_us-gaap_DeferredPolicyAcquisitionCosts_019fcdef-57dd-7d8e-9ebc-cf27abcc85b2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019fcdef-57dd-7b31-b36e-0e99ad78cb05" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74dc-8e0f-9ba109b23386" xlink:to="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019fcdef-57dd-7b31-b36e-0e99ad78cb05" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssets_019fcdef-57dd-7c35-98ee-c5010a7c86ab" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74dc-8e0f-9ba109b23386" xlink:to="loc_us-gaap_OtherAssets_019fcdef-57dd-7c35-98ee-c5010a7c86ab" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Goodwill_019fcdef-57dd-7768-8e2e-16b62f93ffae" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74dc-8e0f-9ba109b23386" xlink:to="loc_us-gaap_Goodwill_019fcdef-57dd-7768-8e2e-16b62f93ffae" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill_019fcdef-57dd-797b-a4c0-693eb1e15043" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74dc-8e0f-9ba109b23386" xlink:to="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill_019fcdef-57dd-797b-a4c0-693eb1e15043" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Investments_019fcdef-57dd-7f44-8cce-ab6cf0e9e909" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74dc-8e0f-9ba109b23386" xlink:to="loc_us-gaap_Investments_019fcdef-57dd-7f44-8cce-ab6cf0e9e909" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrepaidReinsurancePremiums_019fcdef-57dd-774f-a9b6-4a72b7b2e73c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74dc-8e0f-9ba109b23386" xlink:to="loc_us-gaap_PrepaidReinsurancePremiums_019fcdef-57dd-774f-a9b6-4a72b7b2e73c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentNet_019fcdef-57dd-764e-8a69-7afe7afaa198" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74dc-8e0f-9ba109b23386" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentNet_019fcdef-57dd-764e-8a69-7afe7afaa198" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_019fcdef-57dd-7da6-8a27-7eda07ab74fe" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Liabilities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019fcdef-57dd-7c52-b16f-299279dc5829" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7da6-8a27-7eda07ab74fe" xlink:to="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019fcdef-57dd-7c52-b16f-299279dc5829" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnearnedPremiums_019fcdef-57dd-7749-aaa9-2b44b1664a4f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7da6-8a27-7eda07ab74fe" xlink:to="loc_us-gaap_UnearnedPremiums_019fcdef-57dd-7749-aaa9-2b44b1664a4f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsPayableTradeCurrentAndNoncurrent_019fcdef-57dd-763b-90c5-6d5626f68aa4" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7da6-8a27-7eda07ab74fe" xlink:to="loc_us-gaap_AccountsPayableTradeCurrentAndNoncurrent_019fcdef-57dd-763b-90c5-6d5626f68aa4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_019fcdef-57dd-7a39-a335-d0961c59dee8" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7da6-8a27-7eda07ab74fe" xlink:to="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_019fcdef-57dd-7a39-a335-d0961c59dee8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_DeferredCedingCommission_019fcdef-57dd-7672-877a-b0876645c2be" xlink:href="lmnd-20260930.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_019fcdef-57dd-7da6-8a27-7eda07ab74fe" xlink:to="loc_lmnd_DeferredCedingCommission_019fcdef-57dd-7672-877a-b0876645c2be" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsPayable_019fcdef-57dd-7e56-9412-f1584687e22f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7da6-8a27-7eda07ab74fe" xlink:to="loc_us-gaap_CededPremiumsPayable_019fcdef-57dd-7e56-9412-f1584687e22f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCredit_019fcdef-57dd-7f14-87ce-e31e6885337f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7da6-8a27-7eda07ab74fe" xlink:to="loc_us-gaap_LineOfCredit_019fcdef-57dd-7f14-87ce-e31e6885337f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019fcdef-57dd-7782-ab65-c34ee2d17336" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7da6-8a27-7eda07ab74fe" xlink:to="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_019fcdef-57dd-7782-ab65-c34ee2d17336" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Investments_019fcdef-57dd-7cb2-9f76-471cbb77fc51" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Investments"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019fcdef-57dd-7fe8-8a38-fbd4ab5c4942" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7cb2-9f76-471cbb77fc51" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019fcdef-57dd-7fe8-8a38-fbd4ab5c4942" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermInvestments_019fcdef-57dd-7a94-94d6-c24b61cd9ec2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7cb2-9f76-471cbb77fc51" xlink:to="loc_us-gaap_ShortTermInvestments_019fcdef-57dd-7a94-94d6-c24b61cd9ec2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_019fcdef-57dd-78f2-9d1c-b3a12e8eadf9" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapital_019fcdef-57dd-72ef-bbf3-7af0c37dd46d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-78f2-9d1c-b3a12e8eadf9" xlink:to="loc_us-gaap_AdditionalPaidInCapital_019fcdef-57dd-72ef-bbf3-7af0c37dd46d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_019fcdef-57dd-7757-a0cd-0c41de802d04" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-78f2-9d1c-b3a12e8eadf9" xlink:to="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_019fcdef-57dd-7757-a0cd-0c41de802d04" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValue_019fcdef-57dd-74c6-9aca-46969a4dc146" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-78f2-9d1c-b3a12e8eadf9" xlink:to="loc_us-gaap_CommonStockValue_019fcdef-57dd-74c6-9aca-46969a4dc146" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit_019fcdef-57dd-78dc-b4a6-b2e6a897bb70" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-78f2-9d1c-b3a12e8eadf9" xlink:to="loc_us-gaap_RetainedEarningsAccumulatedDeficit_019fcdef-57dd-78dc-b4a6-b2e6a897bb70" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVELOSS" xlink:type="simple" xlink:href="lmnd-20260930.xsd#CONDENSEDCONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVELOSS"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVELOSS" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BenefitsLossesAndExpenses_019fcdef-57dd-7d0a-8530-974cef202cf3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BenefitsLossesAndExpenses"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019fcdef-57dd-7004-b836-246098a80543" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7d0a-8530-974cef202cf3" xlink:to="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019fcdef-57dd-7004-b836-246098a80543" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_OtherInsuranceExpense_019fcdef-57dd-76ec-bcb7-12cd50417ffb" xlink:href="lmnd-20260930.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_019fcdef-57dd-7d0a-8530-974cef202cf3" xlink:to="loc_lmnd_OtherInsuranceExpense_019fcdef-57dd-76ec-bcb7-12cd50417ffb" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ResearchAndDevelopmentExpense_019fcdef-57dd-755e-8475-becc254d0687" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7d0a-8530-974cef202cf3" xlink:to="loc_us-gaap_ResearchAndDevelopmentExpense_019fcdef-57dd-755e-8475-becc254d0687" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SellingAndMarketingExpense_019fcdef-57dd-7f86-ab6b-b41b814ea9e1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7d0a-8530-974cef202cf3" xlink:to="loc_us-gaap_SellingAndMarketingExpense_019fcdef-57dd-7f86-ab6b-b41b814ea9e1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpense_019fcdef-57dd-73bd-906b-3ab63831c04b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7d0a-8530-974cef202cf3" xlink:to="loc_us-gaap_GeneralAndAdministrativeExpense_019fcdef-57dd-73bd-906b-3ab63831c04b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues_019fcdef-57dd-7eff-8eaf-236d75698030" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Revenues"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetInvestmentIncome_019fcdef-57dd-7889-aa9b-aa60b8ef27a0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7eff-8eaf-236d75698030" xlink:to="loc_us-gaap_NetInvestmentIncome_019fcdef-57dd-7889-aa9b-aa60b8ef27a0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_CededCommissionIncome_019fcdef-57dd-7f81-9940-60053693d3fe" xlink:href="lmnd-20260930.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_019fcdef-57dd-7eff-8eaf-236d75698030" xlink:to="loc_lmnd_CededCommissionIncome_019fcdef-57dd-7f81-9940-60053693d3fe" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsEarnedNet_019fcdef-57dd-737d-b8cb-4b2167fac8bb" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7eff-8eaf-236d75698030" xlink:to="loc_us-gaap_PremiumsEarnedNet_019fcdef-57dd-737d-b8cb-4b2167fac8bb" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceCommissionsAndFees_019fcdef-57dd-77c7-af8c-24b5388cd12a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7eff-8eaf-236d75698030" xlink:to="loc_us-gaap_InsuranceCommissionsAndFees_019fcdef-57dd-77c7-af8c-24b5388cd12a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019fcdef-57dd-7fc3-a497-3618c5e10ce5" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BenefitsLossesAndExpenses_019fcdef-57dd-7352-bbad-d54919847be9" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7fc3-a497-3618c5e10ce5" xlink:to="loc_us-gaap_BenefitsLossesAndExpenses_019fcdef-57dd-7352-bbad-d54919847be9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues_019fcdef-57dd-7be7-8e8c-08c38f9d512e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7fc3-a497-3618c5e10ce5" xlink:to="loc_us-gaap_Revenues_019fcdef-57dd-7be7-8e8c-08c38f9d512e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTax_019fcdef-57dd-7c74-aa36-d2dfa42d963a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ComprehensiveIncomeNetOfTax"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019fcdef-57dd-77b3-be20-b8a842ba6a48" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7c74-aa36-d2dfa42d963a" xlink:to="loc_us-gaap_NetIncomeLoss_019fcdef-57dd-77b3-be20-b8a842ba6a48" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeAvailableforsaleSecuritiesAdjustmentNetOfTaxPortionAttributableToParent_019fcdef-57dd-79a7-b12b-58ee36357b98" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7c74-aa36-d2dfa42d963a" xlink:to="loc_us-gaap_OtherComprehensiveIncomeAvailableforsaleSecuritiesAdjustmentNetOfTaxPortionAttributableToParent_019fcdef-57dd-79a7-b12b-58ee36357b98" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeForeignCurrencyTransactionAndTranslationAdjustmentNetOfTaxPortionAttributableToParent_019fcdef-57dd-775b-bc15-5b7f1b31af7a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7c74-aa36-d2dfa42d963a" xlink:to="loc_us-gaap_OtherComprehensiveIncomeForeignCurrencyTransactionAndTranslationAdjustmentNetOfTaxPortionAttributableToParent_019fcdef-57dd-775b-bc15-5b7f1b31af7a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019fcdef-57dd-75e5-a2bd-c16b170c9750" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit_019fcdef-57dd-741b-81ed-a4d55bdcd398" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-75e5-a2bd-c16b170c9750" xlink:to="loc_us-gaap_IncomeTaxExpenseBenefit_019fcdef-57dd-741b-81ed-a4d55bdcd398" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019fcdef-57dd-7611-bde7-bfd4551eead0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-75e5-a2bd-c16b170c9750" xlink:to="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019fcdef-57dd-7611-bde7-bfd4551eead0" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFCASHFLOWS" xlink:type="simple" xlink:href="lmnd-20260930.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_019fcdef-57dd-7115-89ec-072c68b59cae" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019fcdef-57dd-73bf-9ee6-806db3297487" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7115-89ec-072c68b59cae" xlink:to="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019fcdef-57dd-73bf-9ee6-806db3297487" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019fcdef-57dd-7922-bb9c-0a4fb988a6e0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7115-89ec-072c68b59cae" xlink:to="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019fcdef-57dd-7922-bb9c-0a4fb988a6e0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectOfExchangeRateOnCashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019fcdef-57dd-78a1-930e-711500305874" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7115-89ec-072c68b59cae" xlink:to="loc_us-gaap_EffectOfExchangeRateOnCashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019fcdef-57dd-78a1-930e-711500305874" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019fcdef-57dd-7c70-9303-cd6aea48c46d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7115-89ec-072c68b59cae" xlink:to="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019fcdef-57dd-7c70-9303-cd6aea48c46d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019fcdef-57dd-7563-a284-29f0ea1ba778" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_019fcdef-57dd-7b77-ae4d-e9a0f1849882" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7563-a284-29f0ea1ba778" xlink:to="loc_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_019fcdef-57dd-7b77-ae4d-e9a0f1849882" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleAndMaturityOfAvailableForSaleSecurities_019fcdef-57dd-7866-9366-3f41219fd239" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7563-a284-29f0ea1ba778" xlink:to="loc_us-gaap_ProceedsFromSaleAndMaturityOfAvailableForSaleSecurities_019fcdef-57dd-7866-9366-3f41219fd239" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireMarketableSecurities_019fcdef-57dd-74a1-bce6-98b86c9aa85f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7563-a284-29f0ea1ba778" xlink:to="loc_us-gaap_PaymentsToAcquireMarketableSecurities_019fcdef-57dd-74a1-bce6-98b86c9aa85f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_019fcdef-57dd-7efc-8765-2a132f8c14a2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7563-a284-29f0ea1ba778" xlink:to="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_019fcdef-57dd-7efc-8765-2a132f8c14a2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_019fcdef-57dd-7160-a7b9-1b56100818e3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7563-a284-29f0ea1ba778" xlink:to="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_019fcdef-57dd-7160-a7b9-1b56100818e3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019fcdef-57dd-76fc-b8f2-9599dbac73e9" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromLinesOfCredit_019fcdef-57dd-7357-8aae-da113308df9d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-76fc-b8f2-9599dbac73e9" xlink:to="loc_us-gaap_ProceedsFromLinesOfCredit_019fcdef-57dd-7357-8aae-da113308df9d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfLinesOfCredit_019fcdef-57dd-71b6-bc3e-f2a294b08c0b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-76fc-b8f2-9599dbac73e9" xlink:to="loc_us-gaap_RepaymentsOfLinesOfCredit_019fcdef-57dd-71b6-bc3e-f2a294b08c0b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromStockOptionsExercised_019fcdef-57dd-7844-897e-259b6f9659b2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-76fc-b8f2-9599dbac73e9" xlink:to="loc_us-gaap_ProceedsFromStockOptionsExercised_019fcdef-57dd-7844-897e-259b6f9659b2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019fcdef-57dd-7908-b02e-f2e99a7aaa72" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_NetIncomeLoss_019fcdef-57dd-7908-b02e-f2e99a7aaa72" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepreciationDepletionAndAmortization_019fcdef-57dd-78e7-9614-b4ac452e0d3e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_DepreciationDepletionAndAmortization_019fcdef-57dd-78e7-9614-b4ac452e0d3e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensation_019fcdef-57dd-7467-a1f7-ce854d1e8a67" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_ShareBasedCompensation_019fcdef-57dd-7467-a1f7-ce854d1e8a67" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccretionAmortizationOfDiscountsAndPremiumsInvestments_019fcdef-57dd-7c99-879a-e8ae51a37945" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_AccretionAmortizationOfDiscountsAndPremiumsInvestments_019fcdef-57dd-7c99-879a-e8ae51a37945" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProvisionForDoubtfulAccounts_019fcdef-57dd-7d49-b789-7993ccf90eab" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_ProvisionForDoubtfulAccounts_019fcdef-57dd-7d49-b789-7993ccf90eab" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPremiumsReceivable_019fcdef-57dd-72a5-8ff0-e72a5f142dae" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_IncreaseDecreaseInPremiumsReceivable_019fcdef-57dd-72a5-8ff0-e72a5f142dae" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_019fcdef-57dd-7ae6-8fab-cabb3b975747" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_019fcdef-57dd-7ae6-8fab-cabb3b975747" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums_019fcdef-57dd-7a7b-96dd-0705f0743c98" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums_019fcdef-57dd-7a7b-96dd-0705f0743c98" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_019fcdef-57dd-7f7b-940c-c7efb85a5336" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_019fcdef-57dd-7f7b-940c-c7efb85a5336" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets_019fcdef-57dd-734f-97ac-2c882c0c97cc" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets_019fcdef-57dd-734f-97ac-2c882c0c97cc" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_019fcdef-57dd-7371-bca7-c832483d4a33" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_019fcdef-57dd-7371-bca7-c832483d4a33" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInUnearnedPremiumsNet_019fcdef-57dd-70c9-b9cb-3b1ea0d170fa" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_IncreaseDecreaseInUnearnedPremiumsNet_019fcdef-57dd-70c9-b9cb-3b1ea0d170fa" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsPayable_019fcdef-57dd-7790-b667-10ce09613a57" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_IncreaseDecreaseInAccountsPayable_019fcdef-57dd-7790-b667-10ce09613a57" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsurancePayables_019fcdef-57dd-7b00-a793-249bca2fc442" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_IncreaseDecreaseInReinsurancePayables_019fcdef-57dd-7b00-a793-249bca2fc442" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_IncreaseDecreaseInDeferredCedingCommissions_019fcdef-57dd-70e0-9c3e-3f04827e996a" xlink:href="lmnd-20260930.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_lmnd_IncreaseDecreaseInDeferredCedingCommissions_019fcdef-57dd-70e0-9c3e-3f04827e996a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_IncreaseDecreaseInCededPremiumsPayable_019fcdef-57dd-7b9d-9e7f-47cfe0d8bacf" xlink:href="lmnd-20260930.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_lmnd_IncreaseDecreaseInCededPremiumsPayable_019fcdef-57dd-7b9d-9e7f-47cfe0d8bacf" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccruedLiabilitiesAndOtherOperatingLiabilities_019fcdef-57dd-73f9-abcc-4831a67a5fe7" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_IncreaseDecreaseInAccruedLiabilitiesAndOtherOperatingLiabilities_019fcdef-57dd-73f9-abcc-4831a67a5fe7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnTerminationOfLease_01a05770-0c21-7d4c-9eea-4486d8d6688d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainLossOnTerminationOfLease"/>
    <link:calculationArc order="18" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019fcdef-57dd-74ca-b9bd-cade8331b62d" xlink:to="loc_us-gaap_GainLossOnTerminationOfLease_01a05770-0c21-7d4c-9eea-4486d8d6688d" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/SummaryofSignificantAccountingPoliciesCashCashEquivalentsandRestrictedCashDetails" xlink:type="simple" xlink:href="lmnd-20260930.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_019fcdef-57dd-7b68-bdf9-293101e8387b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_019fcdef-57dd-75e2-818b-8ea04d7d9495" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7b68-bdf9-293101e8387b" xlink:to="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_019fcdef-57dd-75e2-818b-8ea04d7d9495" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCash_019fcdef-57dd-7eba-bf5d-eccf6d9d487c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7b68-bdf9-293101e8387b" xlink:to="loc_us-gaap_RestrictedCash_019fcdef-57dd-7eba-bf5d-eccf6d9d487c" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/InvestmentsAmortizedCostandFairValuesofInvestmentinFixedMaturitiesDetails" xlink:type="simple" xlink:href="lmnd-20260930.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_019fcdef-57dd-708f-90e4-bdc1590ec5a5" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_019fcdef-57dd-79a9-9ace-86c91ce89a68" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-708f-90e4-bdc1590ec5a5" xlink:to="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_019fcdef-57dd-79a9-9ace-86c91ce89a68" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_019fcdef-57dd-7012-9987-511045de52ce" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-708f-90e4-bdc1590ec5a5" xlink:to="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_019fcdef-57dd-7012-9987-511045de52ce" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019fcdef-57dd-7714-b856-15e771fec58e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-708f-90e4-bdc1590ec5a5" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019fcdef-57dd-7714-b856-15e771fec58e" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/InvestmentsContractualMaturitiesofBondsDetails" xlink:type="simple" xlink:href="lmnd-20260930.xsd#InvestmentsContractualMaturitiesofBondsDetails"/>
  <link:calculationLink xlink:role="http://lemonade.com/role/InvestmentsContractualMaturitiesofBondsDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasis_019fcdef-57dd-7eb4-8610-a30564795f73" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasis"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesNextRollingTwelveMonthsAmortizedCostBasis_019fcdef-57dd-7b60-a71c-e426417fa180" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesNextRollingTwelveMonthsAmortizedCostBasis"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasis_019fcdef-57dd-7eb4-8610-a30564795f73" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesNextRollingTwelveMonthsAmortizedCostBasis_019fcdef-57dd-7b60-a71c-e426417fa180" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearTwoThroughFiveAmortizedCostBasis_019fcdef-57dd-7100-97aa-a967eab3e4d2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasis_019fcdef-57dd-7eb4-8610-a30564795f73" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearTwoThroughFiveAmortizedCostBasis_019fcdef-57dd-7100-97aa-a967eab3e4d2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearSixThroughTenAmortizedCostBasis_019fcdef-57dd-7b94-bf3f-79de773d3960" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearSixThroughTenAmortizedCostBasis"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasis_019fcdef-57dd-7eb4-8610-a30564795f73" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearSixThroughTenAmortizedCostBasis_019fcdef-57dd-7b94-bf3f-79de773d3960" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingAfterYearTenAmortizedCostBasis_019fcdef-57dd-7390-851f-ba577f9f7f87" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingAfterYearTenAmortizedCostBasis"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasis_019fcdef-57dd-7eb4-8610-a30564795f73" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingAfterYearTenAmortizedCostBasis_019fcdef-57dd-7390-851f-ba577f9f7f87" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019fcdef-57dd-784b-a3ee-5ad2b4d74f6f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDate_019fcdef-57dd-77ee-9cb9-394adeb9be70" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDate"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019fcdef-57dd-784b-a3ee-5ad2b4d74f6f" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDate_019fcdef-57dd-77ee-9cb9-394adeb9be70" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue_019fcdef-57dd-7404-85c2-bac3c3e73194" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019fcdef-57dd-784b-a3ee-5ad2b4d74f6f" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue_019fcdef-57dd-7404-85c2-bac3c3e73194" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019fcdef-57dd-7cbe-8ad9-5c9abd6cdd9e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasis_019fcdef-57dd-739e-8a6a-ef0e29715416" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasis"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019fcdef-57dd-7cbe-8ad9-5c9abd6cdd9e" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasis_019fcdef-57dd-739e-8a6a-ef0e29715416" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost_019fcdef-57dd-759b-9f7e-b45cd399528c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019fcdef-57dd-7cbe-8ad9-5c9abd6cdd9e" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost_019fcdef-57dd-759b-9f7e-b45cd399528c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDate_019fcdef-57dd-763f-85a3-758dd7dc4d87" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDate"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesNextRollingTwelveMonthsFairValue_019fcdef-57dd-7c76-acf7-63367c5f21c7" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesNextRollingTwelveMonthsFairValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDate_019fcdef-57dd-763f-85a3-758dd7dc4d87" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesNextRollingTwelveMonthsFairValue_019fcdef-57dd-7c76-acf7-63367c5f21c7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearTwoThroughFiveFairValue_019fcdef-57dd-71b1-8099-b10e3aef8ca4" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearTwoThroughFiveFairValue"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDate_019fcdef-57dd-763f-85a3-758dd7dc4d87" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearTwoThroughFiveFairValue_019fcdef-57dd-71b1-8099-b10e3aef8ca4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearSixThroughTenFairValue_019fcdef-57dd-7fdb-8639-9886250fa192" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearSixThroughTenFairValue"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDate_019fcdef-57dd-763f-85a3-758dd7dc4d87" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingYearSixThroughTenFairValue_019fcdef-57dd-7fdb-8639-9886250fa192" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingAfterYearTenFairValue_019fcdef-57dd-7a5f-9e8f-4371fd99b4ee" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingAfterYearTenFairValue"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesSingleMaturityDate_019fcdef-57dd-763f-85a3-758dd7dc4d87" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesRollingAfterYearTenFairValue_019fcdef-57dd-7a5f-9e8f-4371fd99b4ee" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/InvestmentsAgingofGrossUnrealizedLossesDetails" xlink:type="simple" xlink:href="lmnd-20260930.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_019fcdef-57dd-71d4-b167-525570d0c8f4" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_019fcdef-57dd-7dcf-87a8-7a6062e4a6e0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-71d4-b167-525570d0c8f4" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_019fcdef-57dd-7dcf-87a8-7a6062e4a6e0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_019fcdef-57dd-7863-a822-63d109022006" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-71d4-b167-525570d0c8f4" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_019fcdef-57dd-7863-a822-63d109022006" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_019fcdef-57dd-70a0-a64b-a9ac7f55892a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_019fcdef-57dd-7822-9218-26f2c702d251" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-70a0-a64b-a9ac7f55892a" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_019fcdef-57dd-7822-9218-26f2c702d251" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019fcdef-57dd-72b5-9076-621132b33a42" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-70a0-a64b-a9ac7f55892a" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019fcdef-57dd-72b5-9076-621132b33a42" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/FairValueMeasurementsFairValueHierarchyforFinancialAssetsandLiabilitiesDetails" xlink:type="simple" xlink:href="lmnd-20260930.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_019fcdef-57dd-7286-ad7f-82036565b85a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetsFairValueDisclosure"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermInvestments_019fcdef-57dd-7314-9f72-583c64f6dde8" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7286-ad7f-82036565b85a" xlink:to="loc_us-gaap_ShortTermInvestments_019fcdef-57dd-7314-9f72-583c64f6dde8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019fcdef-57dd-71a5-8dcf-5949c213c015" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7286-ad7f-82036565b85a" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019fcdef-57dd-71a5-8dcf-5949c213c015" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/UnpaidLossandLossAdjustmentExpenseActivityintheLiabilityforUnpaidLossandLAEDetails" xlink:type="simple" xlink:href="lmnd-20260930.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_019fcdef-57dd-795a-9a2a-c59905b4b85c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForLossesAndLossAdjustmentExpense"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_019fcdef-57dd-7c3f-a4e0-b83c57a48835" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-795a-9a2a-c59905b4b85c" xlink:to="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_019fcdef-57dd-7c3f-a4e0-b83c57a48835" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_019fcdef-57dd-7491-bbd5-bb40c5f005c0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-795a-9a2a-c59905b4b85c" xlink:to="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_019fcdef-57dd-7491-bbd5-bb40c5f005c0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019fcdef-57dd-769b-8a3b-ce8fd3824cd7" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019fcdef-57dd-7694-89c9-7f9d66a974cf" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-769b-8a3b-ce8fd3824cd7" xlink:to="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019fcdef-57dd-7694-89c9-7f9d66a974cf" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019fcdef-57dd-7356-b246-6720b7f9937b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-769b-8a3b-ce8fd3824cd7" xlink:to="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019fcdef-57dd-7356-b246-6720b7f9937b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019fcdef-57dd-7c25-8960-611dfd12ba53" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_019fcdef-57dd-7230-a91a-cd5fe3fe720f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7c25-8960-611dfd12ba53" xlink:to="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_019fcdef-57dd-7230-a91a-cd5fe3fe720f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_019fcdef-57dd-7cd6-9eab-7e52748b0da9" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7c25-8960-611dfd12ba53" xlink:to="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_019fcdef-57dd-7cd6-9eab-7e52748b0da9" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/OtherLiabilitiesandAccruedExpensesDetails" xlink:type="simple" xlink:href="lmnd-20260930.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_01a154a3-95f3-7c11-a631-a1c7f5f4cb6e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccruedLiabilitiesAndOtherLiabilities"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_PayableToCarriers_01a154a3-95f3-718e-a76e-3507d44d3c50" xlink:href="lmnd-20260930.xsd#lmnd_PayableToCarriers"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_01a154a3-95f3-7c11-a631-a1c7f5f4cb6e" xlink:to="loc_lmnd_PayableToCarriers_01a154a3-95f3-718e-a76e-3507d44d3c50" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedAdvertisingCurrentAndNoncurrent_01a154a3-95f3-72f6-a3da-771264d56225" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccruedAdvertisingCurrentAndNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_01a154a3-95f3-7c11-a631-a1c7f5f4cb6e" xlink:to="loc_us-gaap_AccruedAdvertisingCurrentAndNoncurrent_01a154a3-95f3-72f6-a3da-771264d56225" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiability_01a154a3-95f3-7aad-aa2a-8bcacd699f96" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingLeaseLiability"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_01a154a3-95f3-7c11-a631-a1c7f5f4cb6e" xlink:to="loc_us-gaap_OperatingLeaseLiability_01a154a3-95f3-7aad-aa2a-8bcacd699f96" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_UncertainTaxPosition_01a154a3-95f3-7ba3-b8f6-02a7d811d084" xlink:href="lmnd-20260930.xsd#lmnd_UncertainTaxPosition"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_01a154a3-95f3-7c11-a631-a1c7f5f4cb6e" xlink:to="loc_lmnd_UncertainTaxPosition_01a154a3-95f3-7ba3-b8f6-02a7d811d084" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeRelatedLiabilitiesCurrentAndNoncurrent_01a154a3-95f3-79d1-9a2d-e053d135601f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EmployeeRelatedLiabilitiesCurrentAndNoncurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_01a154a3-95f3-7c11-a631-a1c7f5f4cb6e" xlink:to="loc_us-gaap_EmployeeRelatedLiabilitiesCurrentAndNoncurrent_01a154a3-95f3-79d1-9a2d-e053d135601f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_PremiumTaxesPayable_01a154a3-95f3-73e6-8c89-8f01faf67ce3" xlink:href="lmnd-20260930.xsd#lmnd_PremiumTaxesPayable"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_01a154a3-95f3-7c11-a631-a1c7f5f4cb6e" xlink:to="loc_lmnd_PremiumTaxesPayable_01a154a3-95f3-73e6-8c89-8f01faf67ce3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePayable_01a154a3-95f3-786f-a5cc-42cd6dde5f61" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsurancePayable"/>
    <link:calculationArc order="7" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_01a154a3-95f3-7c11-a631-a1c7f5f4cb6e" xlink:to="loc_us-gaap_ReinsurancePayable_01a154a3-95f3-786f-a5cc-42cd6dde5f61" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedProfessionalFeesCurrentAndNoncurrent_01a154a3-95f3-7776-a7df-b55d2e52721b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccruedProfessionalFeesCurrentAndNoncurrent"/>
    <link:calculationArc order="8" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_01a154a3-95f3-7c11-a631-a1c7f5f4cb6e" xlink:to="loc_us-gaap_AccruedProfessionalFeesCurrentAndNoncurrent_01a154a3-95f3-7776-a7df-b55d2e52721b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_AdvancePremiumLiability_01a154a3-95f3-74b0-abe2-e170e057f98b" xlink:href="lmnd-20260930.xsd#lmnd_AdvancePremiumLiability"/>
    <link:calculationArc order="9" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_01a154a3-95f3-7c11-a631-a1c7f5f4cb6e" xlink:to="loc_lmnd_AdvancePremiumLiability_01a154a3-95f3-74b0-abe2-e170e057f98b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestPayableCurrentAndNoncurrent_01a154a3-95f3-7c3e-ae51-eb87e9d11534" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestPayableCurrentAndNoncurrent"/>
    <link:calculationArc order="10" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_01a154a3-95f3-7c11-a631-a1c7f5f4cb6e" xlink:to="loc_us-gaap_InterestPayableCurrentAndNoncurrent_01a154a3-95f3-7c3e-ae51-eb87e9d11534" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedIncomeTaxes_01a154a3-95f3-72e0-93db-91264fc9768e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccruedIncomeTaxes"/>
    <link:calculationArc order="11" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesAndOtherLiabilities_01a154a3-95f3-7c11-a631-a1c7f5f4cb6e" xlink:to="loc_us-gaap_AccruedIncomeTaxes_01a154a3-95f3-72e0-93db-91264fc9768e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherSundryLiabilities_01a154a3-95f3-7b74-9ddb-723b1e2d92a2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_01a154a3-95f3-7c11-a631-a1c7f5f4cb6e" xlink:to="loc_us-gaap_OtherSundryLiabilities_01a154a3-95f3-7b74-9ddb-723b1e2d92a2" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://lemonade.com/role/SegmentInformationScheduleofSegmentReportingInformationbySegmentDetails" xlink:type="simple" xlink:href="lmnd-20260930.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_019fcdef-57dd-7434-bc62-f6d708e14731" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues_019fcdef-57dd-7d82-b617-8429744ee2bb" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7434-bc62-f6d708e14731" xlink:to="loc_us-gaap_Revenues_019fcdef-57dd-7d82-b617-8429744ee2bb" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019fcdef-57dd-79ba-a8df-394642197678" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7434-bc62-f6d708e14731" xlink:to="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019fcdef-57dd-79ba-a8df-394642197678" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_OtherInsuranceExpense_019fcdef-57dd-7414-9569-39956c19c866" xlink:href="lmnd-20260930.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_019fcdef-57dd-7434-bc62-f6d708e14731" xlink:to="loc_lmnd_OtherInsuranceExpense_019fcdef-57dd-7414-9569-39956c19c866" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SellingAndMarketingExpense_019fcdef-57dd-784f-9de8-15c9050563a2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7434-bc62-f6d708e14731" xlink:to="loc_us-gaap_SellingAndMarketingExpense_019fcdef-57dd-784f-9de8-15c9050563a2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdvertisingExpense_019fcdef-57dd-7bb7-bf59-fb21298c2acd" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7434-bc62-f6d708e14731" xlink:to="loc_us-gaap_AdvertisingExpense_019fcdef-57dd-7bb7-bf59-fb21298c2acd" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ResearchAndDevelopmentExpense_019fcdef-57dd-72ea-8813-975d62a5522a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7434-bc62-f6d708e14731" xlink:to="loc_us-gaap_ResearchAndDevelopmentExpense_019fcdef-57dd-72ea-8813-975d62a5522a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_lmnd_GeneralAndAdministrativeLessInterestDepreciationAndOtherSegmentIncomeExpenses_019fcdef-57dd-7023-8457-b536dbb7c643" xlink:href="lmnd-20260930.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_019fcdef-57dd-7434-bc62-f6d708e14731" xlink:to="loc_lmnd_GeneralAndAdministrativeLessInterestDepreciationAndOtherSegmentIncomeExpenses_019fcdef-57dd-7023-8457-b536dbb7c643" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpenseNonoperating_019fcdef-57dd-742d-8875-ce624a3ba81b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7434-bc62-f6d708e14731" xlink:to="loc_us-gaap_InterestExpenseNonoperating_019fcdef-57dd-742d-8875-ce624a3ba81b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostOfGoodsAndServicesSoldDepreciationAndAmortization_019fcdef-57dd-785f-be1e-a3369703559d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7434-bc62-f6d708e14731" xlink:to="loc_us-gaap_CostOfGoodsAndServicesSoldDepreciationAndAmortization_019fcdef-57dd-785f-be1e-a3369703559d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingOtherItemAmount_019fcdef-57dd-74c5-8464-5106ff1e1b00" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7434-bc62-f6d708e14731" xlink:to="loc_us-gaap_SegmentReportingOtherItemAmount_019fcdef-57dd-74c5-8464-5106ff1e1b00" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit_019fcdef-57dd-7ab1-b989-3dfd69495f64" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_019fcdef-57dd-7434-bc62-f6d708e14731" xlink:to="loc_us-gaap_IncomeTaxExpenseBenefit_019fcdef-57dd-7ab1-b989-3dfd69495f64" xlink:type="arc"/>
  </link:calculationLink>
</link:linkbase>
