This chapter focuses on race, sexuality, and self-monitoring by exploring the language practices of black gay men. We show how black gay men use language to creatively navigate the double-bind of homophobia in some black communities and the widespread racism found in predominantly white gay male communities. In our analysis of the speech of one black gay man (Bakari), we examine how he monitors his language and comportment as he constructs a black gay identity. Bakari creates the persona of an “ambassador,” which affords him more acceptance within discriminatory contexts, at least temporarily. We show how individuals who are both sexual and racial minorities use a complex set of linguistic resources in order to navigate the harmful, discriminatory discourses that they face in their daily lives.