The role of sexual networks in the epidemiology of human immunodeficiency virus (HIV) among black men who have sex with men (MSM) is poorly understood. Using data from 1,306 black MSM in the BROTHERS Study (2009-2010) in the United States, we examined the relationships between multiple sexual dyadic characteristics and serodiscordant/serostatus-unknown condomless sex (SDCS). HIV-infected participants had higher odds of SDCS when having sex at least weekly (odds ratio (OR) = 2.41, 95% confidence interval (CI): 1.37, 4.23) or monthly (OR = 1.94, 95% CI: 1.17, 3.24) versus once to a few times a year. HIV-uninfected participants had higher odds of SDCS with partners met offline at sex-focused venues (OR = 1.79, 95% CI: 1.15, 2.78) versus partners met online. In addition, having sex upon first meeting was associated with higher odds of SDCS (OR = 1.49, 95% CI: 1.21, 1.83) than was not having sex on first meeting, while living/continued communication with sexual partner(s) was associated with lower odds of SDCS (weekly: OR = 0.64, 95% CI: 0.47, 0.85; monthly: OR = 0.60, 95% CI: 0.44, 0.81; yearly: OR = 0.58, 95% CI: 0.39, 0.85) versus discontinued communication. Persons with primary/steady nonprimary partners versus commercial partners had lower odds of SDCS regardless of HIV serostatus. This suggests the need for culturally relevant HIV prevention efforts for black MSM that facilitate communication with sexual partners especially about risk reduction strategies, including preexposure prophylaxis.