Freud's ‘Little Hans’ and Melanie Klein's first case study of ‘Fritz’ are read alongside a contemporary popular film to consider the tensions of sexual enlightenment, a goal first articulated by Freud and later rejected by Klein. These documents represent conundrums of gender-as relation, phantasy, and defense. They do not settle our understanding of how gender and sexual difference develop but, rather, proffer ideas for reading gender and sexuality as a particular story of the limits, dilemmas, pleasures, and strange turns of events in education and psychoanalysis for adults and children. A child's questions on gender may animate contemporary discussions and regard for the libidinal qualities of trying to know one's gender through encountering the other. My focus on the libidinal qualities of trying to know gender, and so the self, emphasizes the pleasure, passions, and misconstrual for knowledge and ignorance. What remains is the question of the archive and its uncertain future.