This paper brings together different strands of my research interests in contemporary formations of gender and sexuality, the history of feminist thought, and the aesthetic practices of clinical writing. I focus on the question of ‘woman’, variously constructed and contested since the time of Freud’s writing, exploring how psychoanalytically informed feminism can contribute to contemporary cultural debates on what many have termed the transgender moment. Specifically, I pursue the hypothesis that a formal alliance pertains between the methodological question of the case study and the cultural question of gender as it has found expression from the 1960s on.