Data from a cohort of young HIV-negative gay and bisexual men were analyzed to identify determinants of sexual risk-taking at baseline. Gay/bisexual men aged between 18 and 30 completed a self-administered questionnaire including demographics, depression, social support, substance use, and consensual versus nonconsensual sex. Risk-takers were defined as those who had unprotected anal sex with casual male sex partners in the previous year; non-risk-takers were defined as those who reported consistent condom use during anal sex with all male partners in the previous year. Logistic regression was used to identify independent predictors of sexual risk-taking. Of 439 men studied, risk-takers had less education, a higher depression score, less social support, and were more likely to report nonconsensual sex and recreational drug use relative to non-risk-takers. Independent predictors of sexual risk-taking were low education, nitrite use, low social support (adjusted odds ratio [AOR]=1.65; 95% CI, 1.04-2.59), and nonconsensual sex experienced as a youth or adult (AOR=1.85; 95% CI, 1.15-2.96). Young gay/bisexual men reporting nonconsensual sex, low social support, or nitrite use were significantly more likely to have recently had unprotected anal sex with casual partners. HIV prevention programs aimed at young gay/bisexual men should include sexual abuse counselling and foster community norms supporting safer sex practices.