Although condom use is an effective barrier against HIV transmission, some men who have sex with men (MSM) engage in bareback sex (unprotected anal sex in risky contexts) and increase their risk for HIV (re)infection. Understanding MSM's decision to bareback (vis-à-vis condom use) is essential to develop effective HIV/AIDS prevention programs for this population. An ethnically diverse sample of men who bareback (n = 120) was recruited exclusively on the Internet and stratified to include two thirds who reported both unprotected receptive anal intercourse (URAI) and being HIV uninfected. We used exploratory factor analysis to explore the domains within the Decisional Balance to Bareback (DBB) scale, and test the association between DBB and risky sexual behaviors. HIV-positive MSM (n = 31) reported higher costs/losses associated with condom use than HIV-negative men (n = 89). We found two underlying factors in the DBB scale: a Coping with Social Vulnerabilities subscale (eight items; alpha = .89) and a Pleasure and Emotional Connection subscale (five items; alpha = .92). We found a positive association between DBB (i.e. greater gains associated with bareback sex) and URAI occasions, number of partners, and having one or more sero-discordant partners in the past 3 months. We conclude that because MSM may avoid using condoms in order to cope with psychosocial vulnerabilities and create intimacy with other MSM, this population could benefit from alternatives to condoms such as pre/post exposure prophylaxis and rectal microbicides.