Psychoanalysis has, from Freud's earliest ideas, been drawn to comprehending and defining gender—decoding what is masculine and what is feminine. Although Freud believed that masculinity and femininity would normatively fall along biological lines, gender, as a category, very quickly became destabilized by theorists who contested Freud's view. This article looks at a case in which the analyst came to view the patient's gender performance as a form of protest as it became transacted within the transference-countertransference relationship. In drawing upon contemporary gender and relational psychoanalytic theories, the author considers the multiple layers of gender meanings held within the patient and within the analyst and concludes that gender is never fully resolved and will continue to carry shifting relational meanings.