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This paper explores how a sample of recent Afro-Cuban immigrants negotiate race and identity in the United States by examining how they respond to being questioned on almost a daily basis about their racial, ethnic, and linguistic ambiguity in two of the nation’s most diverse cities. While some inquiries are a matter of simple curiosity, other questions denote the persistence of binary racial thinking among people of various racial/ethnic backgrounds including established "white" Cubans in Miami, Florida; African Americans; and people of Mexican origin in Los Angeles, California. The 30 respondents interviewed for this project demonstrate how in these cases they draw on their multiple identities to undermine fixed expectations about identity and propriety with the use of specific strategies, such as humor, pretense, anger, and confrontation. As post-Cuban revolutionary immigrants, Cubans, Blacks, and Spanish speakers, their multiple consciousness allows them the ability to have foreknowledge and anticipate how others perceive them and how to respond. As such, they disrupt binary racial thinking by playing with dominant (mis) perceptions. Focusing on how these Afro-Cuban interviewees respond to the questioning of their multiplicity and rejection of their blackness by various groups, we obtain important insight into the particular and varied ways populations perceived to be “ambiguous” negotiate identity in the complex and diverse ethnic/racial terrain of 21st century America.