Intimate relationships have received increasing attention as a context for HIV transmission. We examined the relationships among perceptions that condoms interfere with intimacy, gay-related stigma, and unprotected/protected anal intercourse. Participants included 245 single-identified men who have sex with men. Intimacy Interference was positively associated with number of unprotected anal intercourse acts, and this effect was stronger among participants who reported high levels of gay-related stigma. In contrast, Intimacy Interference was negatively associated with number of protected anal intercourse acts, and gay-related stigma was positively associated with this outcome with no evidence of interaction effects. The findings are explained in the context of rejection sensitivity theory, and implications for public health and clinical intervention are discussed.