In this study, we compared internalizing and externalizing problem behavior of 67 Dutch adolescents (M _age = 16.04) in planned lesbian families who were matched with 67 adolescents in heterosexual-parent families. We also examined whether homophobic stigmatization was associated with problem behavior in adolescents with lesbian mothers after taking into account demographic characteristics, mothers' scores on emotional involvement, and adolescents' earlier problem behavior (measured at age 4–8 years old). Standardized instruments measuring problem behavior were completed by parents and adolescent offspring, and questions about stigmatization were answered by adolescents with lesbian mothers. The results revealed no differences in internalizing and externalizing problem behavior associated with family type. Offspring in lesbian families who reported more experiences of homophobic stigmatization also demonstrated more internalizing and externalizing problem behavior.