Today, psychoanalysis struggles to integrate rapidly developing ideas of gender identity, sex, and sexuality without falling back on normative models. Clinicians are faced by the challenge of encountering transgender people seeking treatment in a quickly changing and multi-polarized cultural environment. In this paper, my aim is to present some of the theoretical and epistemological questions implied in the often-polarized debate about how to understand and help transgender people requesting our help. My concern is the risk of holding on to a biological binary model of sex and a dogmatic understanding of the oedipal complex as well as the danger of pathologizing transgender patients. The paper underscores that facing the clinical and theoretical challenge of gender diversity and – fluidity has the potential to be creative for our field and for those we try to help.