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Drawing on 53 in-depth history interviews with college-educated Black men, I argue that to understand why some Black middle-class (BMC) men choose non-Black women also requires an understanding of the evolution of both their inter and intra racial experiences overtime. Existing quantitative research has importantly identified that degreed, high earning Black men are more likely to have an interracial relationship. But, these cross-sectional surveys rarely capture the trajectory of the same individuals over the life course or move us beyond their marital outcomes with white women. Focusing on the intragenerational mobility patterns of BMC men, I find that while there were differences in how respondents who have experienced steep or consistent upward mobility explained their interracial relationship decisions, both discussed it in relation to the nature and quality of their experiences with Black women. That is, their intra-racial relationships were important experiences for making sense of their interracial decisions. These findings challenge the implication that BMC men’s interracial relationships signify a lack of desire for Black women.