A substantial proportion of undergraduate men report compliance with unwanted, noncoercive sexual activities. This study used thematic analysis of interviews with 12 undergraduate men to understand how they conceptualized compliance with unwanted sex. Themes emerging within the context of casual sexual encounters were: compliance with unwanted sex is socially beneficial; alcohol modifies one’s sexual receptivity to unwanted sex; and men rarely anticipate negative consequences from sexual compliance. Themes emerging within the context of committed relationships were: being compliant with unwanted sex for altruistic reasons and to build intimacy; and it is okay to say no to sex. Within the context of casual relationships, men’s understanding and expectations of compliance with unwanted, noncoercive sex were complex and deeply rooted in their conceptualization of masculinity on a personal and social level.