Sexual victimization has been shown to positively relate to both engagement in risky behavior and subsequent sexual victimization. Research has focused on the degree to which women consider the risks or costs of engaging in risky behaviors. The purpose of the current study was to examine the degree to which women weigh the costs and benefits of engaging in risky behaviors. Using self-report data from 113 female undergraduates, two separate hierarchical regression analyses were performed to examine the contributions of number of sexual victimization experiences, emotion dysregulation, cost expectations of risky behavior, and benefit expectations of risky behavior to latency to exit a risk perception vignette involving a stranger and frequency of engagement in risky behavior. Regression analyses revealed that the full set of predictors accounted for 13% of the variance in latency to exit the risk perception vignette involving a stranger, with emotion dysregulation and benefit expectations making significant and independent contributions. Regression analyses revealed that the same set of predictors accounted for 34% of the variance in frequency of engagement in risky behavior, with number of sexual victimization experiences and benefit expectations making significant and independent contributions. The current findings suggest that sexual victimization risk may be influenced by perceived benefits of risky behavior. Implications of the current findings will be discussed in the context of sexual victimization risk reduction.