This study examines how hegemonic masculinity is upheld in the formation and maintenance of cross-sexual orientation friendships between college aged men. Broadly defined, hegemonic masculinity prizes that which is masculine, and subordinate that which is considered feminine, including non-heterosexual identities for men. The practices of hegemonic masculinity establish a hierarchy that perpetuates the dominant social position of heterosexual men, and the subordinated position of women and those men with non-heterosexual identities. Drawing on 40 interviews with 20 self-identified queer and 20 straight men at a large public university in the south, this study finds that while the masculine hierarchy is central to both the formation (or non-formation) and maintenance of cross-sexual orientation friendships, the hierarchy is of greater importance to the queer men in these associations. Regarding the formation of these friendships, queer men expressed anxiety regarding entering into these associations, commonly citing past experiences of homophobia, fear of coming out, and the lack of desire for friendship on the part of the straight male as the chief reasons for their apprehension for entering into these associations. Juxtaposed with other studies, the present study found that straight men reported little anxiety about entering into these associations: most reported that these friendships would likely offer them greater disclosure than their other friendships. Once formed, queer men in these friendships often policed themselves so as to not make their sexual identity salient, queer men put more work into maintaining these friendships, and interactions between straight and queer male friends were found to differ when in public and private spaces. These results point to cross-sexual orientation friendships between men as an avenue through which the masculine hierarchy is not diminished, but rather mutually upheld by queer and straight men alike.