Women’s auto/biography provides powerful and culturally diverse narratives. The traditional odyssey for the inner meaning of the female self often involves a search for the maternal legacy. Through a series of conversations that were enacted in various locations significant to the authors, the telling of partial and subjective stories of maternal histories were narrated. The two authors have known each other for more than 55 years having started school together at the age of four. Through their conversations, they sought to gain a fuller understanding of different representations of connections among, and between, women. Stories were told of mothers and daughters as well as sisters and friends. The focus of the conversations was on how a Catholic upbringing and education seeps into the intergenerational relationships of mothers and daughters and infuses the contradictions and polarities of women’s lives.