What does a psychoanalytic inquiry into the interactions between the patient's and analyst's gender, sexual orientation, and ethnicity look like? To answer this question, the author examines the relationship between a white gay male analyst and his straight female patient of color through the dual lens of queer theory and interpersonal/relational psychoanalysis. The article describes the psychoanalytic process of moving beyond dissociated, binary modes of perceiving one's self and the other. This interpersonal process involves acknowledging the shame- and guilt-riddled aspects of patient's and analyst's experiences of privilege and marginalization. The author maintains that a playful, curious, and soul-searching engagement in enactments can lead to the emergence of a transitional space in which the sexual and ethnic similarities and differences between patient and analyst can be acknowledged, challenged, and negotiated.