Counseling psychologists are tasked with understanding optimal psychological and cognitive functioning. Recent theoretical predictions (Crisp & Turner, 2011) and growing evidence suggest that cross-race interactions are important ways individuals might improve their cognitive and psychosocial functioning. However, the theoretical predictions from Crisp and Turner have not yet been tested in one model. Further, much of the empirical support for the theoretical predictions has been from studies using 1) undergraduate samples and 2) weak theory-measurement fit. The present study used an online, community survey (N = 270) to test Crisp and Turner’s (2011) predictions that cognitive flexibility would mediate the relationship between cross-race interactions and psychological well-being in both a White sample (N = 198) and a sample of Color (N = 70). Results supported the hypothesized mediational model, indicating that more frequent cross-race interactions were associated with greater psychological well-being, through greater cognitive flexibility. The findings are discussed in the context of Crisp and Turner’s model (2011). Implications for sociological, educational, and psychological professionals are also discussed. Recommendations for future studies include experimental, longitudinal, and intervention studies with strong theory-measurement fit.