This chapter uses three stories of young women’s relationships with their parents to increase our understanding of Christianity’s impact on classic familial values in late antiquity. It is focused on the ways in which the famous second century story of the virgin Thecla, and her difficult relationship with her mother Theocleia, was read and reused in later Christian stories. In the Passion of Eugenia we see how Thecla’s story becomes a catalyst for the eponymous heroine to follow Thecla’s example and reject the marriage proposed for her. She does so, however, without creating the rift with her parents that Thecla’s departure necessitates. That careful reuse demonstrates the developing uncertainty over whether the rise of Christian asceticism necessitated the destruction of the traditional household. In Gregory of Nyssa’s Life of Macrina, we see the Cappadocian bishop again using Thecla to think with, as he feels his way towards a new solution to this same problem. These case studies not only show us the changing landscape of Christian thinking on marriage, family, and asceticism, but also reveal the complex matrix of meanings latent in the original Acts of Paul and Thecla.