The image of the model minority dominates scholarly and public discourse on Asian American children and adolescents. However, recent research has shown that despite their high levels of educational achievement Asian American students report poor psychological and social adjustment. Using an ecological framework, this article sought to explore the family and peer experiences of Chinese American adolescents as these are the two most critical contexts influencing adolescents' psychological and social adjustment. Drawing on longitudinal data collected from two studies conducted in Boston and New York on 120 first- and second-generation Chinese American students, our analyses suggested that many Chinese American adolescents feel alienated from their parents and peers. The alienation from parents was due to factors such as language barriers, parenting work schedules, and high parental educational expectations. Alienation from peers was due to ongoing peer discrimination from both Chinese and non-Chinese peers. Implications and future research are also discussed. (Contains 1 table.)