Data from 984 “men-seeking-men” Craigslist.org postings in five cities were analyzed to assess differences in sexual requests, HIV status disclosure, and negotiated safety between young (18-24 years) and older (25 years and older) men who have sex with men (MSM). Young MSM were less likely than older MSM to post their HIV status or the preferred status of a partner (p=0.04), disclose and/or request a partner who was disease and drug free (p=.01), and request use of a condom in their posting (p=0.01). Interventions aimed at changing the culture and content of postings on Craigslist.org by encouraging HIV status disclosure and condom use preference are warranted, particularly for young MSM