This article compares the education, employment, and care work biographical sequences of Canadian and German women and men from late adolescence into mid-adulthood. Through the lenses of comparative gendered life course theory and welfare regime theory, sequence and cluster analyses are used to determine the adult life course sequences of women and men in each country and to assess the extent to which they differ across contexts. The analyses reveal clear gender differences in work–family balance in labour market participation and unpaid care work. Groups also differ strongly on educational attainment, income, and family composition. Comparatively, gender differences are less marked in the Canadian context. These results suggest that differing gendered trajectories result in diverse outcomes depending on the national context, shaping different outcomes for women cross-nationally. Our findings highlight how historical and contemporary country-specific welfare state policies support or hinder women as active and productive members of society.