Recent investigations have explored dispositional optimism as a determinant of various health-related behaviors, though such research has been infrequently conducted in populations where pessimism would be expected to be prevalent. The present study examines optimism and unsafe sexual behavior in 230 sexually active inner-city minority adolescents. Findings suggest that dispositional optimism is a protective factor regarding adolescents' intentions to avoid engaging in unsafe sex. Further, the benefits of optimism appear to be explained by those who are more optimistic having higher levels of perceived condom use self-efficacy and stronger negative expectancies toward unsafe sex. Future interventions may need to address optimism in concert with behavioral-specific determinants to increase the probability of reducing unsafe sexual behavior in high-risk populations.