This study used data collected from a sample of 840 Italian adolescents (418 boys; M age = 12.58) and their parents (657 mothers; M age = 43.78) to explore the relations between parenting, adolescent self-disclosure, and antisocial behavior. In the hypothesized model, parenting practices (e.g., parental monitoring and control) have direct effects on parental knowledge and antisocial behavior. Parenting style (e.g., parent-child closeness), on the other hand, is directly related to adolescent self-disclosure, which in turn is positively related to parental knowledge and negatively related to adolescents' antisocial behavior. A structural equation model, which incorporated data from parents and adolescents, largely supported the hypothesized model. Gender-specific models also found some gender differences among adolescents and parents, as the hypothesized model adequately fit the subsample of mothers but not fathers. Mothers' closeness to girls predicted their knowledge of their daughters' behavior; mothers' control predicted boys' antisocial behavior.