Using diary methods, the current study explored characteristics of young adults' sexual risk interactions over a two-week period and the associations between perceived risk and safety with regard to these sexual risk behaviors. We screened all participants to ensure a moderate to high scores on an HIV knowledge measure. Men (n = 44) and women ( n = 48) enrolled at an inner-city college collected diary data, generating reports of 440 sexual occasions over a 2-week period (1,278 person-days). Despite participation in sexual risk activities, including highly inconsistent condom use during intercourse, participants uniformly reported high safety and little to no risk. Only women's perceptions of safety (not risk) were associated with condom use, men's perceptions of both safety and risk were unrelated. Ratings of safety and risk appeared to operate independently for the most part. Sex with new partners and new sexual activity were associated with both judgments of greater risk and lower safety were associated for men only. These results add to the growing evidence that young people fail to integrate fully their general knowledge regarding HIV risk into their personal interactions. This study has implications for the development of cognitive models around sexual decision-making for young adults at risk for HIV and may provide insight into the contextual features of sexual interactions associated with young people's perceptions of risk and safety.