We conducted face-to-face semi-structured interviews with 50 men recruited from the New York City men-seeking-men section of Craigslist.org. Participants discussed their favorite venues for meeting sex partners (n = 28 said the Internet), and we focused on these men's responses to probes regarding decisions around condom use and HIV status disclosure with online partners. A majority indicated they set a priori rules for themselves to always use condoms, and they cited the Internet as their favorite venue in part because it helped them sort for like-minded partners. Participants indicated that having in-person conversations around condom use and HIV was often difficult, and that the Internet was a convenient medium to facilitate the process. Notable differences were observed in how HIV-positive and HIV-negative men navigated serostatus disclosure-HIV-negative men were less subtle in starting the conversation. Finally, participants described a common narrative around distrust with online partners, which is one reason why they consistently use condoms. These data suggest that features which allow men to easily indicate, and filter for, condom use preferences should be built into (or maintained on) profile-based sexual networking sites and sexual bulletin board sites.