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A 3-wave model linking natural mentoring relationships to externalizing behavior was tested with 345 rural African American emerging adults in their final year of high school. Structural equation models were executed linking multi-informant reports of mentor-emerging adult relationship quality with youths’ externalizing behavior 18 months later. Consistent with our primary hypotheses, emerging adults whose relationships with their natural mentors were characterized by instrumental and emotional support and affectively positive interactions reported lower levels of anger, rule-breaking behavior, and aggression. These effects emerged independent of the influences of family support and youth gender. Two intrapersonal processes, a future orientation and self-regulation, emerged as mediators of the influence of natural mentoring relationships. The influence of natural mentors was most pronounced for …