Millions of people around the world use Geo-Social Networking Applications (GSNAs) to connect with new people and potential sexual partners. Using data from a broad study of GSNA users, this paper explores GSNA use by straight men and the implications on their positionality, masculinity, and for their leisure. Straight men showed that although they speak out against traditional masculine norms in their offline lives, on GSNAs they enact and embrace hegemonic norms of dating. This dualistic (re)presentation demonstrates some of the complexities of how contemporary leisure spaces (like dating) become digitally mediated, but maintain deep human-to-human involvement and traditionalist social expectations.