By sharing the lived experiences of Chinese descendants who grew up in the United States, this article highlights the complex and dynamic interactions that occur when navigating between Chinese and Euro American cultures. We focus on two groups of Chinese descendants: one raised by Chinese immigrant families and the other raised by Euro American families in the United States. While both groups may be considered "Chinese American," distinctive parental ethnic backgrounds and different cultural exposures seem to have created different challenges for these individuals during bicultural socialization and identity development. Through this article, we hope to heighten the need to take complex sociocultural contexts into account because racial and cultural issues in social interactions are prominent in people with more complex cultural backgrounds. This discussion could be useful for clinical practitioners who provide multicultural counseling services to foster psychological wellbeing, tolerance, and acceptance.