Asian Americans are commonly defined by two seemingly opposite racial stereotypes. On the one hand, they are cast as perpetual foreigners, and so not fully accepted as Americans, regardless of their nativity or years of living in the United States (Devos & Banaji, 2005; Lee, Lee, & Tran, 2016; Wu, 2002). On the other hand, they are typically seen as model minority figures—hard-working and problem-free (Wu, 2002; Yoo, Burrola, & Steger, 2010). Racial triangulation theory (Kim, 1999) posits that these two stereotypes together have created a unique racial position for Asian Americans and that this position both impedes social and economic opportunities and is an obstacle to their general well-being. However, we know little about how Asian Americans make sense of this unique racial positionality and how it, in turn, influences the development of Asian American young people. Using the data from the Midwest Longitudinal Study of Asian American Families (MLSAAF), a longitudinal survey study of Filipino American and Korean American children and their families in the Chicago metropolitan area, this study first examines whether there are any identifiable patterns of racial stereotype profiles [based on the perpetual foreigner stereotype (PFS) and the model minority stereotype (MMS), including the model minority stereotype-achievement orientation (MMS-Achievement), and the model minority stereotype-unrestricted mobility (MMS-Mobility)] among sample groups of Filipino American and Korean American adolescents and emerging adults. In addition, the direct effects of racial stereotypes and their interaction effects on internalizing and externalizing behavioral outcomes are examined. Finally, this study explores whether and how these moderating relations further vary by developmental stage (adolescence vs. emerging adulthood), nativity (U.S.-born vs. foreign-born), and gender (female vs. male) within each ethnic group. The findings highlight the importance of investigating the concurrent effects of racial stereotypes in better understanding the racialized experiences of Asian Americans and their implications on the development of young Asian Americans. The study further suggests that these relations may vary by important social positions such as developmental stage, nativity, gender, and ethnicity. Practical implications are discussed in terms of how the results of this study can inform the development of programmatic interventions that would aim to protect Asian American young people from the harmful effects of being stereotyped by front-line clinicians and school staff.