The painful experiences of an adolescent boy treated in analytically oriented psychotherapy are used as a lens through which we can consider the effects of homophobia, their internalization, and their entanglement with intrapsychic processes. Controversies in the psychoanalytic literature on internalized homophobia are also considered. Homophobia within the developmental literature and the nascent state of conceptualizations of healthy homosexual development are addressed as concerns for treatment and pedagogy. I examine elements of my countertransference, including an overly cautious attitude toward exploring contradictory or complex aspects of my patient's sexuality due to a concern not to replicate homophobic attitudes. I also discuss some of the implications for coming out at a young age, as this boy did.