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Adolescents have begun to initiate sexual activity at increasingly early ages in the past few decades. Using a sample of 2,494 adolescents from the National Longitudinal Survey of Youth (NLSY97), structural and parental process variables were examined in the prediction of sexual onset. Results indicated that the age at which youth initiate sexual intercourse is related to the structural characteristics of their grandmothers and mothers, as well as puberty, gender, and race. There is support for partial mediation of the effects of these grandmother characteristics via mother characteristics and parental process. Results are discussed within the framework of the life course perspective and provide support for the importance of previous generations in the explanation of adolescent sexual behavior. Implications for families and adolescents are also addressed.