Friendships are crucial for well-being (Narr et al., 2019), and this may particularly be the case for gay men (Nardi, 1999; Nardi & Sherrod, 1994). One-way friendships have been understood is through the lens of gender segregation, which posits that same-gender friendships are more appropriate and safer than cross-gender friendships, due to a presumed lack of sexual or romantic interest between same-gender friends and similarities in communication preferences. This assertion may not hold true for gay men; however, gay men continue to report close and supportive friendships with other men. In the present study, we qualitatively explored gay men’s same-gender friendships to better understand how sexual orientation and gender influence the development and maintenance of these friendships through interviews with 15 men in the United States. In friendships with heterosexual men, participants reported heterosexism, homophobia, and self-disclosure as potential barriers, but they also reported feeling accepted by their heterosexual friends. In terms of friendships with other gay men, some participants described avoiding friendships with gay men while others reported finding community with gay men. Finally, participants described different ways in which they perceived their sexual orientation to impact their friendships. Taken together, our findings suggest that gender norms and sexual orientation play a role in how gay men experience their friendships with gay and heterosexual men.