This study investigated the role of children's gender stereotypes and peer playmate experiences in shaping their desire to play with peers who hold counterstereotypical preferences (e.g., a boy who likes dolls or a girl who likes trucks). Children (N = 95; 46 girls, 49 boys; 67% White, 18% Black, 8% Latinx, 4% Asian, 3% other; median household income = $US97,810) who were 4 to 8 years old (M = 6.11 years old, SD = 1.34) were interviewed about their gender stereotypes about toy preferences, how often they engage in counterstereotypical playmate experiences, and their desire to play with peers who hold counterstereotypical toy preferences. Children with less gender stereotype-consistent expectations reported more playmate experiences with children who played with toys that were gender counterstereotypical compared to children with more gender stereotype-consistent expectations. Additionally, children with less gender stereotype-consistent expectations reported a greater desire to play with peers who held counterstereotypical toy preferences compared to children with more gender stereotype-consistent expectations. Younger children's reported playmate experiences with peers who liked toys that were gender counterstereotypical and their desire to play with these peers were strongly related to their gender stereotypical expectations (and more so than for older children). Together, these findings indicate that children's gender stereotypes and peer playmate experiences are related to their desire to play with peers who hold counterstereotypical toy preferences, highlighting the importance of facilitating diverse friendships for promoting inclusive orientations in childhood.