This study assessed whether the relationship between using the Internet to meet sex partners and unprotected anal intercourse (UAI) differs for men who have sex with men (MSM) living in rural and urban areas. Data on Internet use, residence and UAI were collected from MSM attending Gay Pride events in 12 U.S. cities. Rural MSM who used the Internet to meet sex partners were more likely to report any UAI (adjusted odds ratio[AOR]: 1.89 [1.12–3.19]) and insertive UAI (AOR: 2.16 [1.13–4.10]) with the last sex partner than those who did not use the Internet. For urban MSM, UAI was not more commonly reported by men who used the Internet to meet sex partners. The association between using the Internet to meet sex partners and UAI depended on whether MSM resided in rural or urban areas. Rural MSM may have different patterns of risk behavior from urban MSM. The Internet may offer new prevention opportunities for rural MSM.