Family-based interventions targeting parenting factors, such as parental monitoring and parent-child communication, have been successful in reducing adolescent offenders' substance use and delinquency. This pilot, exploratory study focuses on family and parenting factors that may be relevant in reducing juvenile offenders' substance use and sexual risk taking behavior, and in particular examines the role of family emotional involvement and responsiveness in young offenders' risk-taking behaviors. Participants included 53 juvenile drug court offenders and their parents. Results indicate that poor parent-child communication is associated with marijuana use and unprotected sexual activity for young offenders; however, family affective responsiveness is also a significant unique predictor of unprotected sexual activity for these youth. Findings suggest that interventions focused on improving parent-child communication may reduce both marijuana use and risky sexual behavior among court-involved youth, but a specific intervention focused on improving parents and young offenders' ability to connect with and respond to one another emotionally may provide a novel means of reducing unprotected sexual risk behaviors.