Venue-based characteristics (e.g., alcohol in bars, anonymous chat online, dark/quiet spaces in bathhouses) can impact how men who have sex with men (MSM) negotiate sex and HIV-associated risk behavior. We sought to determine the association between HIV-associated risk factors and the venues where MSM met their most recent new (first-time) male sex partner, using data from a 2004 to 2005 national online anonymous survey of MSM in the U.S. (n = 2,865). Most men (62%) met their partner through the Internet. Among those reporting anal sex during their last encounter (n = 1,550), half had not used a condom. In multivariate modeling, and among men reporting anal sex during their last encounter, venue where partner was met was not significantly associated with unprotected anal intercourse (UAI). Nevertheless, venue was related to other factors that contextualized men's sexual encounters. For example, HIV status disclosure was lowest among men who met their most recent partner in a park, outdoors, or other public place and highest among men who met their most recent partner online. Alcohol use prior to/during the last sexual encounter was highest among men who met their most recent partner in a bathhouse or a bar/club/party/event. These data suggest it is possible to reach men online who seek sex in many different venues, thus potentially broadening the impact of prevention messages delivered in virtual environments. Although not associated with UAI, venues are connected to social-behavioral facets of corresponding sexual encounters, and may be important arenas for differential HIV and STI education, treatment, and prevention.