Parents shape their adolescents’ gender role attitudes through the process of gender role socialization. How parents socialize their adolescent’s gender role attitudes has long-lasting impacts on how youth navigate social relationships, envision work and family roles, and enforce or reject gender stereotypes. Adolescence is a period in which romantic interests, peer involvement, and identity formation are rapidly developing, making it important to understand how parents contribute to their adolescents’ gender role attitude development (i.e., expectations for women’s and men’s behavior and social roles; Galambos et al., 2009; McHale, Crouter, & Tucker, 1999). Evidence suggests that parents may socialize their children differently depending on their own and their adolescent’s gender (i.e., parent-child gender constellation; McHale et al., 2003; Ruble et al., 2006). The aim of this study is to examine parents’ accounts of how they socialize gender in their adolescent daughters and sons using open-ended responses from mothers and fathers (N = 60 parents) in 30 White, working and middle-class families with both an adolescent daughter and son. Parke and Buriel’s (1998) tripartite model of socialization served as a guide to analyze parents’ socialization practices within three pathways: parent-child interaction, parents as instructors, and parents as providers of opportunities. Symbolic interactionism provided a lens through which to understand how gender roles are socially constructed. Parents revealed gender socialization practices that were inconsistent with their own attitudes, fit within the tripartite model socialization, and were unique to each parent-child gender constellation. Understanding parents’ gender socialization practices can be useful to help practitioners who work with families, so they can better support parents in becoming more aware and intentional about how they may be socializing gender differently depending on their own and their child’s gender.