This paper uses the lens of Relational-Cultural Theory (RCT) to analyze data from a qualitative study of sexual fluidity in long-time lesbians who became intimately partnered with men. The analysis illuminated processes of shame, disconnection, authenticity, and connection. As RCT would predict, severe disconnection from individuals and community through silencing, shaming and marginalizing resulted in psychological pain (hurt, guilt, shame, isolation, grief, despair and depression), while authenticity and connection served to promote or restore well-being. Rigidly categorical models of sexual identity that are unable to accommodate sexual fluidity likely contribute to the oppression of sexual minorities in both heterosexual and sexual minority cultures.