Many gifted Asian American adolescent males face cultural issues that may impact their success. This article presents important cultural dilemmas faced by 2 gifted Asian American young men. Through a qualitative approach, the acculturation experiences of John and Matt, gifted Taiwanese, second generation immigrants, are described. Intergenerational cultural conflict in the families of the young men is examined. Implications for supporting Asian parents in nurturing their sons' social, emotional, and intellectual development are discussed. The following are appended: (1) Sample Interview Questions Used With Participants John and Matt; and (2) Sample Interview Questions Used With the Participants' Mothers.