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To evaluate a model of social contextual influences on risk for adolescent pregnancy, 368 target adolescents (52% female, 48% male) and their mothers, fathers, and closest age siblings were assessed 6 times over a 7-year period beginning when the target adolescents were in 7th grade. Two pathways were found to increase risk for involvement in a pregnancy by late adolescence. Middle adolescent risk-taking behavior mediated the influence of early adolescent parental warmth–involvement and deviant-peer affiliations on involvement in a pregnancy by 12th grade. Also, early adolescent academic competence mediated the relationship between parental warmth–involvement and involvement in a pregnancy by 12th grade. Theoretical and practical implications of the results are discussed.