We examine both gay and straight men’s constructions of masculinity using 358 self-descriptive dating profiles from Match.com of "men seeking men" and "men seeking women" in eight southern US metropolitan areas. In addition to the men’s specific references to gender and gendered performances, we discuss three broad topics of the men’s self-descriptions including personality, leisure, and work. This analysis reveals the ideal characteristics these men used to construct their own masculine identities and masculinity in relation to femininity. Although examples of conformity and nonconformity existed across both gay and straight men, we found that gay men constructed their own identities in keeping with the codes of historically heteronormative masculinities as fluently, and sometimes more so, than straight men. We explore the most prominent nuances between gay and straight men’s paths to claiming "masculine capital," straight men’s greater leeway to temporarily distance themselves from masculine dominance, and the influence of hierarchies within masculinity on straight and gay men’s constructions of femininity.