In the context of a U.S. dominant masculinity ideology, which devalues men who are not heterosexually identified, many gay, bisexual and questioning (GBQ) adolescent males must develop their own affirming and health-promoting sense of masculinity. In order to promote the well-being of GBQ young men, exploration of their reactions and responses to dominant images of masculinity is needed. We qualitatively analyzed interviews with 39 GBQ African American, Latino, and European American male adolescents (15-23 years old). Participants reported a range of responses to traditional masculinity ideologies, most of which centered on balancing presentations of masculine and feminine characteristics. Negotiation strategies served a variety of functions, including avoiding anti-gay violence, living up to expected images of masculinity, and creating unique images of personhood free of gender role expectations. These data suggest a complex picture of GBQ male adolescents' management of masculinity expectations and serve as a basis for culturally and developmentally specific HIV prevention programs.