Asian American adolescents' cross-race friendships are poorly understood, partially due to the model minority stereotype. Using data from 915 Asian American adolescents from the National Longitudinal Study for Adolescent to Adult Health, the present study examined the influence of cross-race friendships (based on peer nomination data) on Asian American adolescents' psychological well-being trajectories, as well as the moderating role of school context (numeric marginalization, school prejudice). Results showed that cross-race friendships promoted Asian American adolescents' psychological well-being, particularly in early adolescence and in schools where adolescents lacked critical mass of same-race peers or where prejudice was widespread. Similar findings were observed for cross-race friendships with the majority group, and more evident effects emerged for cross-ethnic friendships.