Every year thousands of Western men travel to Thailand as sex tourists to participate in paid-for sex. Although many of these men will use condoms to protect themselves against sexually transmitted infections (STIs), others will not, despite the risks. By applying Steven Lyng's (1990) concept of edgework to data collected from 14 face-to-face interviews with male sex tourists in Pattaya, Thailand, and 1,237 online discussion board posts, this article explores the ways in which these men understood and sought to rationalize the sexual risks they took. We argue that notions of likelihood of infection and significance of consequence underpin these behaviors, and we identify the existence of understandings of sexual risk that reject mainstream safer-sex messages and frame condomless sex as a broadly safe activity for heterosexual men. The article concludes by summarizing the difficulties inherent in driving behavior change among this group of men, for whom sexual risks appear to be easily rationalized away as either inconsequential or irrelevant.