Young men who have sex with men (YMSM) in the United States are experiencing an alarming increase in HIV incidence. Recent evidence suggests that the majority of new HIV infections in YMSM occur in the context of serious relationships, which underscores the importance of examining predictors of sexual risk behavior in the context of sexual partnerships, including relationship type, sexual partner characteristics, and relationship dynamics. The current study aimed to evaluate relationship and sexual partnership influences on sexual risk behavior in YMSM, including differentiating between multiple sexual risk variables (i.e., any unprotected anal or vaginal intercourse, unprotected insertive anal or vaginal intercourse, and unprotected receptive anal intercourse). More serious/familiar partnerships were associated with more sexual risk across all three risk variables, while wanting a relationship to last was protective against risk across all three risk variables. Some variables were differentially linked to unprotected insertive sex (partner gender) or unprotected receptive sex (partner age, partner race, believing a partner was having sex with others, and partners repeated across waves). Sexual risk behavior in YMSM is inconsistent across sexual partnerships and appears to be determined in no small part by sexual partner characteristics, relationship dynamics, and sexual role (i.e., insertive or receptive partner). These influences are critical in understanding sexual risk in YMSM and provide important targets for intervention.