Purpose - To explore certain aspects of women's experience of their reproductive lives, in different cultural contexts, especially their views on sexuality and sexual practices. It is based on transnational comparative research, and compares the experiences and meanings about motherhood and mother/daughter relationships, especially referring to sexuality and reproductive health. The two contexts we have chosen for this chapter are drawn from our data on Indonesian and Canadian women. While these women come from culturally diverse situations, we find continuities between their experiences as well as contrasts in the contexts in which they live their reproductive lives. Methodology - Our study was based on collecting participant driven narratives focused on their experience of their reproductive lives. We interviewed women from three generations in the same families to secure a longitudinal perspective and to examine the relationships between generations in the same family. Our overall purpose was to examine the role of local culture in the social reproduction of women's lives in the family. Findings - The findings we discuss in this chapter focus on the continuities and contrasts we found in women's experience as lived in very different cultural, religious, and political contexts. Indonesian and Canadian women are struggling to live healthy and meaningful lives in a world that is changing ideologically, culturally, politically, and economically. We identify some key problems faced by women, especially as they negotiate the difficult terrain of sexuality, and suggest some points of entry in solving them. Originality/value - The originality of the article lies in the close examination of in-depth, qualitative data on family relationships, especially in contrasting cultural situations. We also think that our approach, which focuses on generations of women in the same families, provides us with a unique perspective on how relationships and especially women's experience of their reproductive and sexual lives are closely related to the way in which culture is mediated in families.