The dominant narrative of psychoanalysis or psychoanalytically oriented therapy has concerned the male analyst or therapist and the female patient. When one turns, however, to the work of women therapists with male patients—a relationship that reverses many of the assumed orderings between men and women—the impact of the gender of the participants on the therapeutic dialogue becomes more salient. In this article, two issues that are distinctive to the woman therapist—the contradictory terrain of female authority and the meaning of intimacy with women given the residues of the separation-individuation process—are explored in relationship to the treatment of male patients. The preoedipal maternal transference, the possible defensive uses of the erotic transference, and the merging of aggressive and sexual impulses are discussed vis-à-vis the dyad of the woman therapist and the male patient. Finally, it is suggested that this dyad provides a particularly translucent microcosm for addressing a variety of broader questions about gender arrangements in our culture.