Gender and power are theoretical constructs linked to discussions of sexual transmission of HIV/AIDS among heterosexual couples. Despite the fact that HIV rates are rising among young men who have sex with men in the United States, work examining the role of gender in sexual decision making of young men who have sex with men remains in its infancy. Through qualitative interviews with 34 young gay men (YGM), the authors seek to contribute to the literature in this area by focusing on the ways that YGM understand and enact sexual positions during anal sex. The authors’ results highlight the diversity of YGM’s sexual preferences, as well as the high degree of sexual fluidity. Ideas of gender appear to inform part of this process; however, YGM critiqued conventional gender norms and emphasized the centrality of relationships (i.e., casual vs. romantic) in their sexual decision making. The authors discuss the importance of considering gender and interpersonal factors when designing HIV/AIDS prevention messages for YGM.