Against the backdrop of contemporary debates around constructions of masculinities, and explorations concerning how gender figures in psychotherapeutic process, personal reflections are presented by a male psychoanalytic therapist practicing in South Africa. A reflexive, contextual, and historicized conversation is offered, highlighting the precariousness of masculine identities, and their melancholic response to contextual dislocation within a society in transition and in relation to the decline of patriarchal authority. The observations offered emphasize the importance of maintaining a self-reflective stance in order to grapple with normative gender biases and stereotypic assumptions and to reduce the probability of gendered enactments in clinical practice.