More and more we see adolescents coming into the therapeutic space with precise and clear demand to be supported through their transition. What is new is that it is no longer their parents sending them. These adolescents are working on their own accord; they take advice from media, internet, from other adolescents and from TV shows. What is also new is that the decision to transition does not seem to be accompanied by anxiety or ambivalence. Instead, enthusiasm follows a form of adolescent ruthlessness that is grounded in the conviction of being born “in the wrong body”. Given the supple nature of the adolescent, when thinking about treatment, how do therapists understand the desire for gender transitioning? The concern over the transitioning adolescent’s future involve, on the one hand, a worry over regret, and on the other, the fear that the child’s agony over gender may lead to suicide. Both concerns present a challenge to the analyst’s neutrality. How does the analyst meet the ruthlessness of the adolescent patient’s demand? Can the analyst be ruthless in his thinking and reorienting of his work?