Men’s body dissatisfaction is prevalent and a serious health concern as it is associated with negative outcomes including depression, disordered eating, and anabolic steroid abuse. Gay men are particularly vulnerable to body dissatisfaction, perhaps due to heightened sociocultural appearance pressures experienced in gay subculture. Appearance conversations represent an underresearched, but potentially potent, mechanism of appearance pressures. The current study explored whether differences in the frequency of engaging in appearance conversations accounted for differences in body dissatisfaction and associated risk factors among gay and heterosexual men. A purposeful sample of gay (N = 77, Mage = 32.57) and heterosexual (N = 78, Mage = 25.30) men were recruited from community organizations in the United Kingdom. Participants completed an online questionnaire assessing appearance conversations, body dissatisfaction, appearance orientation, and internalization of appearance ideals. Gay men reported more frequent engagement in positive and negative appearance conversations and greater body dissatisfaction, appearance orientation, and general internalization than heterosexual men. Moreover, frequency of appearance conversations mediated the relationship between sexuality and the majority of study variables, including body dissatisfaction (ps < .05). These findings suggest that appearance conversations are an important sociocultural influence on male body image and that they are important in understanding the differences between gay and heterosexual men’s body dissatisfaction and associated risk factors.