In this article, I draw on the experiences of students who participated in the Council on International Educational Exchange (CIEE) Program in Spanish Language and Caribbean Studies, in Santiago, Dominican Republic, from 2000 to 2004, to situate the seemingly conflicting racial projects of the Dominican Republic and the United States. I discuss how, for African Americans and Dominicans, the question of race is actually very similar when it becomes a question of color as Blackness and mixedness are situated processes that encompass ideas of ancestry as well as phenotypic expression in both countries. I argue that racial discourses, and the politics surrounding race and color, for Dominicans in the United States, and African Americans in the Dominican Republic, is very similar because of historical colorization—which I define as intragroup racial and color-naming practices. I suggest that growing interactions between African Americans and Afro-Dominicans, and a growing understanding of race and the racial systems in both the United States and the Dominican Republic, contribute to how identities are being reconstructed. Particularly, African Americans in the Dominican Republic and Dominicans in the United States encounter a racial dilemma—how one is racially defined within a new national context as categories are often based on the state's own definitions, series of laws, and informal ways of classifying people based on skin color.