This paper explores psychotherapeutic themes and modes of thought emerging in interviews with mothers and daughters participating in a cross-generational study of young women 'on the margins'. The focus of the discussion is two-fold. First it discusses current theoretical debates concerning the ascendancy of psychotherapeutic modes of constituting the self, and argues that we require closer attention to the gendered and differentiated ways in which these are registered and articulated. Second, it considers the significance of 'happiness' and the ways in which pairs of mothers and daughters draw upon a repertoire of psychotherapeutic discourses to represent their relation to schooling, self, family, and work. It concludes with some speculative observations about the significance of attending to the psychotherapeutic turn for understanding contemporary femininity, the desire for openness as a measure of a good relationship (and of democracy), and contemporary aspirations of happiness.