Freud's psychoanalytic mode of thought, especially as interpreted by William Grossman, functions as an inherently non-normative means of analyzing both the psychic life of the individual and various historical and cultural phenomena. Application of this mode of thought to particular characterizations of gender and sexuality makes possible an essential critique of trait psychology and static formulations of human development, as restricting both clinical practice and theory building. An exploration of the complexities of sexuality and gender in gay men shows how Freud's insistence on variability lends conceptual power at the intersection of classical psychoanalysis, with its problematic history, and the many clinical and theoretical manifestations of contemporary psychoanalysis. The non-normative psychoanalytic mode of thought developed by Freud must be integrated with more recent formulations about gender and sexuality in order to conduct a psychoanalysis.