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Various studies have underscored the relevance of community-level factors to sexual behavior and HIV/AIDS prevention efforts in Africa. However, there is a paucity of research and theorizing in this area compared to the preponderance of prevention models that focus solely on individual-level factors. Using data from the Cape Area Panel Survey and hierarchical linear models, this study examines the effects of a combination of individual-level factors and community-level poverty on sexual behaviors.Male and female respondents who perceived themselves to be at great risk of HIV infection were less likely to indulge in risky sexual behaviors. For females, race and community-level poverty were confounded such that race mediated the effects of community-level poverty. Results from this study indicate that multiple rationalities affect sexual behaviors in Cape Town, South Africa and that there is a need to consider both the social embeddedness of sexual behaviors and the rational components of decision making when designing HIV/AIDS prevention programs.