Research indicates that high numbers of gay and bisexual men report infrequent or inconsistent condom use, placing them at risk for HIV and other STDs. The present study examined positive and negative condom-related attitudes along three dimensions-risk reduction, pleasure reduction, and intimacy interference-and examined their relative predictive power in determining condom use among a sample of sexually risky gay and bisexual men in New York City. In a multivariate model, both risk reduction and intimacy interference attitudes emerged as significant predictors of unprotected sex; however, the variance accounted for by a model including intimacy interference was almost three times that accounted for by a model including risk reduction alone. These data suggest a pivotal role for intimacy in shaping condom attitudes and behavior among gay and bisexual men. HIV prevention interventions should consider incorporating intimacy as a motivating factor for sexual behavior and a potential barrier to condom use.