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Purpose: To examine whether family, individual, peer and school characteristics are associated with the transition to a first sexual experience with a partner who is three or more years older., Methods: Using multinomial logistic regressions, we analyzed a sample of female teens from the National Longitudinal Study of Adolescent Health to assess risk and protective factors associated with having a first sexual experience with a partner three or more years older, compared with a similar-aged partner and compared with not engaging in sexual intercourse., Results: Younger and foreign-born teens, with lower parent education, with older friendship networks, and attending a school that spans multiple grades, had greater odds of having a first sexual experience with an older partner than with a similar-aged partner. Hispanics and premenarche females had lower odds of having an older sexual partner than of abstaining from sexual intercourse. In contrast, older age, lower parent education, nonintact family structure, less connection to and more communication with parents, substance use or having peers who used substances, and having older peers were associated with increased odds of having sex with an older partner, compared with not engaging in sexual intercourse., Conclusion: The findings underscore the importance of educating teens about the risks associated with dating and sexual relationships with older partners, and of educating parents to be especially attentive to the age composition of their teens' circle of friends. Our research has implications for families and program providers, by identifying target risk groups in need of potential prevention efforts.