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Gay life on the Internet has rapidly expanded over the past decade, leaving some to lament the demise of established forms of gay social life. The Internet as a forum for dating and arranging casual sex has been a particular growth practice in Australian gay life. In this essay, the author reflects on his own experiences of Internet dating in the late 1990s in Sydney, and ponders why he is reluctant to re-enter the world of gay Internet dating. The author draws on social theories of liquid modernity to discuss his ambivalence with Internet dating and online assignations, whilst acknowledging the productive possibilities of virtuality.