The primary goal of this study was to examine the relationship between adolescent-parent communication and adolescent internalizing problems. Both gender of the adolescent and gender or the parent were considered. An additional goal was to explore whether coping skills mediated this relationship. The sample included a community sample of 980 U.S. high school students. Surveys were administered during three annual assessment waves in seven public high schools during the spring of 2007 (Time 1), 2008 (Time 2), and 2009 (Time 3). Path analysis results indicated significant direct effects only for same-sex adolescent-parent dyads. For boys, adolescent-father communication predicted depressive and anxiety symptoms. Coping did not mediate these relationships. For girls, adolescent-mother communication predicted anxiety symptoms. Further, this relationship was mediated by humor coping. Adolescent-mother communication also predicted depressive symptoms via instrumental social support for girls. These results align with social learning theory and suggest that family-based interventions with same-sex adolescent-parent dyads are warranted to prevent internalizing problems in adolescents.