In 2002, the prevalence of HIV among South African clinic attendees under the age of 20 was 15 percent, suggesting a correspondingly high level of unprotected sex and risky sexual behavior. Past research focused on the dynamics of individuals’ and partners’ sexual decisionmaking without accounting for the larger context in which such decisions are made. Do adolescents’ opportunities for schooling, work, and other community activities make a difference? This study uses data collected from a representative sample of young people living in KwaZulu‐Natal, South Africa, to explore these questions. Logit analyses show that for girls, higher levels of education reduced the probability of having had sex in the 12 months prior to the survey, and average wages were positively associated with condom use. Greater participation in community sports increased risk‐taking behaviors among boys but decreased them among girls. Within the household, education of adults had a positive effect on condom use for both boys and girls.