Highly sexually active men who have sex with men (MSM) are a critical population in which to provide HIV prevention and education. To inform the tailoring and placement of such services, this study reports on HIV status differences in nine venues where 50 highly sexually active MSM (defined as those who had nine or more male partners in the past 90 days) met recent male sex partners. HIV-positive men (95%) were significantly more likely than HIV-negative/unknown status men (68%) to have used the Internet to meet partners but were less likely to meet partners in bars/clubs (37% vs. 71%). Although both HIV-positive and HIV-negative/unknown status men reported a sizable portion of their total partners from the Internet (55% and 29%, respectively), HIV-positive MSM also gravitated toward meeting partners through sexual networks (private sex parties and via other sex partners), whereas HIV-negative/unknown status also gravitated toward gay bars/clubs and public cruising. Overall, HIV-positive men were more likely to report unprotected anal sex than to HIV-negative/unknown status men. Among HIV-negative/unknown status men, the highest rates of unprotected sex were with men they met online (20% of online partners) and through other sex partners (25% of these partners). Efforts targeted toward highly sexually active HIV-negative/unknown status men might be best positioned online and in gay bars/clubs, whereas those tailored for highly sexually active HIV-positive men may consider targeting the Internet and peers/sexual networks.