This paper adds to the growing but still sparse body of psychoanalytic literature that explores the role of gender in transference and countertransference enactments. The author contends that gender inscription can create a kind of conflict of interest between certain female analysts and certain male patients, especially around attachment, autonomy, and authority. The result may be an undercurrent of anger in which both participants in the analytic dyad dissociate. Here, the focus is on how one female analyst found she dissociated anger because of internalized stereotypical gender restraints, and how her male patients likewise dissociated their anger at her. Using material from her male patients and attuning to her own personal experience, the analyst illustrates how she and her patients were ultimately able to acknowledge their angry feelings and then transform them into a more authentic and mature, hence therapeutic, dialogue.