What does it mean to want to know when the subject is gender? Psychoanalysis, like medicine, has often presumed that evidence can secure certainties in advance. Yet its practice shows otherwise: evidence here is not predictive or cumulative but transformational, emerging in the shifting textures of address, affect, and relation. This essay reframes disputes over gender-affirming care through four dilemmas that have long unsettled psychoanalysis: evidence, history, authority, and the condition of gender itself. Drawing on Kuhn's paradigms, Forrester's case-thinking, and Stengers's critique of neutrality, I argue that debates over “weak” or “strong” evidence repeat the transference—anxieties about helplessness and the demand for certainty—whether in the clinic or in public controversy, from the Cass Review to D'Angelo's critique. Clinical vignettes and transition memoirs show how meaning becomes legible only belatedly, through Nachträglichkeit, and how authority often functions less as knowledge than as defense against uncertainty. I am not proposing treatment guidelines but specifying an analytic stance under conditions of uncertainty, one whose evidentiary force shows itself in practice. Although gender is my site of inquiry, the stakes extend: to inherit psychoanalysis is to accept this wager—that what unsettles today may return tomorrow as the beginning of thought.