This paper analyzes the case of John, an older gay male patient in treatment with a younger gay male therapist. Particular emphasis is placed on the role of aging in the gay community, given the cultural shifts in the definition and meaning of gay identity at this time. Focus is on the tension between the older gay patient's feelings of resentment and disrespect for a younger gay cohort embodied by the therapist, who at times feels pity or frustration, with particular stress on the embrace of an outsider status throughout treatment. The therapy provides a wonderful opportunity to deconstruct this dynamic by exploring the generational difference within a context of treatment.