In this article, the author suggests that training institutes transmit contradictory messages about the sexual boundary in psychoanalysis; these contradictions result in an ambiguous law, and a breakable taboo. These ambivalent transmissions are traced back to the erotic conflicts and cultural contexts that shaped the early work of Breuer, Freud, and Jung. The formulation of psychoanalysis proceeded in a patriarchal, Judeo-Christian culture; this marked Eros with splitting, and with quasireligious features of ecstasy and sin. The author suggests that these tropes were enacted, and inscribed on, the sexual boundary. This inscription has yielded dysfunctional encounters with erotic transference, as clinicians move between seductive excess, erotic avoidance, and sexual transgression. These positions have been replayed throughout the generations, and require a cultural critique. This critique is illustrated through experience near portraits of analysis and supervision.