The relationship of chronic self-destructiveness and hopelessness to risk-taking behaviors was examined. College undergraduates (131 men, 114 women) completed the Beck Hopelessness Scale (Hopelessness), Chronic Self-destructiveness Scale (Self-destructiveness), and Expected Involvement Scale (Involvement) of the Cognitive Appraisal of Risky Activities questionnaire. For both men and women, there were significant positive correlations between Self-destructiveness and Hopelessness scores. In men, there also were positive relationships between Self-destructiveness scores and Involvement in specific risky activities in the next 6 mo. These included illicit drug use, aggressive or illegal behaviors, risky sexual behaviors, heavy drinking, and irresponsible academic or work behaviors. In women, Self-destructiveness scores had a positive relationship with expected Involvement in heavy drinking and irresponsible academic or work behaviors. The only correlation between Hopelessness and Involvement scores for men was a negative one with expected participation in high risk sports. There were no significant correlations between Hopelessness and Involvement scores for women.