The link between adolescent sexual activity and psychological well-being is a controversial issue in developmental psychology. This cross-sectional study investigated the association between three aspects of teenage sexuality (genital sexual experience, age of sexual onset, and number of sex partners) and positive well-being (hedonic, eudaimonic, and overall) in a sample of 475 high school seniors (48% female; 89% White) from a single school district in a rural upstate New York community. Based on a group-norms perspective, we expected higher well-being in adolescents whose sexual behaviors followed group-normative patterns. As expected, sexually experienced and on-time (at age 16) students reported higher well-being than sexually inexperienced or late-onset (17 or older) students. Contrary to expectations, a high number of sex partners and an early sexual onset (15 or younger) were not related to lower well-being. Early-onset girls reported higher levels of well-being than normative-onset peers. Findings are discussed in relationship to theoretical perspectives and past empirical findings of teenage sexuality as a developmental asset versus risk.