This study examines transitions in schooling, sexual activity, and pregnancy among adolescents and young adults in urban South Africa. Data are analyzed from the Cape Area Panel Study (CAPS), a recently collected longitudinal survey of young adults and their families in metropolitan Cape Town. We find that teen pregnancy is not entirely inconsistent with continued schooling, especially for African (black) women. More than 50 percent of African women who were pregnant at age 16 or 17 were enrolled in school the following year. We estimate probit regressions to identify the impact of individual and household characteristics on sexual debut, pregnancy, and school dropout between 2002 and 2005. We find that male and female students who performed well on a literacy and numeracy exam administered in 2002 were less likely than those who performed more poorly to become sexually active and less likely to drop out of school by 2005. Surprisingly, 14–16-year-olds who had completed more grades in school in 2002, conditional on their age, were more likely than those who had completed fewer grades to have become sexually active by 2005, a potential indicator of peer effects resulting from the wide dispersion in age per grade in South African schools. Overall, this study shows the importance of accounting for a measure that reflects the knowledge and skills of young people in an examination of their transitions to adulthood.