This book explores the connection between family structure and circumstances, parental engagement, and adolescent sexual behavior. Given that South Africa contains the highest portion of the global HIV epidemic within a single country, a comprehensive, book-length investigation into—sometimes risky—adolescent sexual behaviour is necessary. Drawing from the longitudinal Cape Area Panel Study (CAPS) of more than 4,000 adolescents between the ages of fourteen and twenty-two, as well as qualitative interviews and focus group discussions with parents and adolescents, this study pioneers empirical investigation of adolescent sexual behavior within the intricate framework of family dynamics in South Africa.