This chapter examines an oral history interview between the author, a white gay scholar, and Curtis Wadlington, a long-time activist around issues of safe sex and HIV prevention in Philadelphia’s African American community. During the interview, Wadlington made references to his own attraction to men, and told stories of same-sex intimacy between men in his neighbourhood, but actively resisted being labelled as “gay”. This chapter looks to Wadlington’s own personal history of engagement with white gay activists in Philadelphia, as well as theoretical interventions in the study of Black queer and sexuality studies by Marlon B. Ross and Darlene Clark Hine, to understand the omissions, elisions, and evasions in his interview. In this way, the chapter offers insight into the practice of interviewing across lines of racial difference and the operation of power and privilege in the interview context.