Most previous studies of the sexual behaviors of men who have sex with men (MSM) living with HIV are based on samples recruited within relatively urban and suburban areas of rhe United States. Using an internet-based questionnaire, we assessed HIV-related stigma, loneliness, and event-level sexual behaviors in a sample of HIV positive MSM (n = 100) residing within a largely rural area in the Midwestern United States. HIV-related stigma was correlated with loneliness (r = 0.619, p < 0.01). Loneliness was negatively associated with condom usage with the most recent partner of unknown status (p < 0.05). Namely, a 1-unit increase in the UCLA loneliness score was met with a 10% decrease in odds of condom usage. Further studies are warranted that explore loneliness, within the context of HIV-related stigma, among HIV-positive MSM residing in rural areas. More refined data will inform clinical and social service practice, as they provide much-needed information on sexual health outcomes and experiences of an often underserved and under studied population.