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The capacity of transgender to incorporate all gender variance and sexual preferences has become a powerful tool of activism and personal identification. Rather than being an index of marginality “trans” has become a central cultural site. In this paper, I will argue that this identity label encompasses a complex range of internal psychic positions in relation to consciously stated sexual preferences and gender identifications. My aim is to explore what can appear to be in some cases a premature embracement of the empowering potential of the transgender identification through my work with under 18-year-olds who are seeking medical intervention for gender dysphoria. This can undermine the painful psychic work required to establish what transgender means for any given young person. In an external culture where to ask “why transgender” (as opposed to “how transgender”) is felt to be pathologising, working with these young people can prove difficult for the analyst. The challenge is to tread the fine line between a dialogue based on an equidistant curiosity about meaning and function that is core to an analytic approach, and a posture of implicit skepticism.