The author surveys his work with gay and bisexual men and his evolving clinical understanding, spanning a thirty-five-year period from 1965 to 2000. Four cases are discussed briefly, one from each decade, to illustrate the changing clinical approach, and the following conclusions drawn: (1) sexual orientation and mental health should be approached as independent dimensions; (2) heterosexual orientation is not a required outcome for successful analysis; (3) an analytic process focused on uncovering a presumed “pathological etiology” inevitably distorts the process and obscures more relevant analytic needs; (4) unrecognized heterosexist assumptions and unfamiliarity with norms of gay men's lives pose special barriers to analytic work with gay men. Ongoing self-analysis and self-education are necessary to reduce interferences that keep analysts from listening to their gay patients with open and unbiased attention.