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To assess whether men who have sex with men (MSM) are more likely to report unprotected anal intercourse (UAI) with partners met on-line compared with those met off-line.A total of 6122 individuals consented to participate in an anonymous behavioral survey on-line. This event-based analysis is limited to the 1683 men from the United States and Canada who had sex in the 3 months before the study and reported that their last sexual encounter included a new or casual male partner or partners. Prevalence and predictors of UAI were analyzed separately for the 386 men reporting more than 1 partner (multiple) and the 1297 men reporting only 1 (single) partner in their last encounter.Of the 1683 MSM recruited on-line, 51% met their partner(s) in their last sexual encounter on-line and 23% reported UAI. No difference in risk for UAI was found for partners met on-line versus off-line in the bivariate or multivariate analyses. In a multivariate analysis of men with multiple-partner encounters, UAI was significantly associated with being HIV-seropositive (adjusted odds ratio [OR] = 2.87; P = 0.02) in a model that included age; education; whether partners were met on-line or off-line; and use of crystal methamphetamine, sildenafil, or alcohol before sex. Using the same model, significant predictors of UAI in men reporting a single-partner encounter were use of crystal methamphetamine (adjusted OR = 5.67; P = 0.001) and no college degree (adjusted OR = 1.63; P = 0.01).MSM recruited on-line who reported a new or casual sex partner(s) in the prior 3 months are at considerable risk of HIV or other sexually transmitted infections, but they are equally likely to report UAI whether sex partners were met on-line or off-line. The Internet may be an ideal venue for reaching high-risk MSM.