The complexity of adolescents’ dating and sexual lives is not easily operationalized with simple indicators of dating or sexual activity. While building on prior work that emphasizes the “risky” nature of adolescents’ intimate relationships, we assess whether a variety of indicators reflecting the complexity of adolescents’ relationships influence early adult well-being (i.e., depressive symptoms, self-esteem, gainful activity, intimate partner violence, and relationship quality). Our analysis of longitudinal data from the Toledo Adolescent Relationships Study showed that the number of adolescent dating and sexual partners does not uniformly influence indicators of young adult well-being, which is at odds with a risk framework. The number of dating partners with whom the individual was sexually active, and not the number of “casual” sex partners, increased the odds of intimate partner violence during young adulthood. Relationship churning and sexual nonexclusivity during adolescence were associated with lower relationship quality during young adulthood. Sexual nonexclusivity during adolescence influenced self-reports of depressive symptoms and lower self-esteem among young adults. Future research should develop more nuanced conceptualizations of adolescent dating and sexual relationships and integrate adolescent dating and sexual experiences into research on early adult well-being. © 2014 Wiley Periodicals, Inc.