HIV disproportionately impacts young African American men who have sex with men (MSM). In this study, we sought to understand how previous relationship experiences and expectations for romantic relationships influence condom use among young African American MSM. Twenty African American MSM aged 16 to 24 years completed a semi-structured interview and questionnaire on sexual experiences, romantic relationships, and sexual behavior. We identified three major themes characterizing romantic male-male relationships: (1) partner selection, (2) relationship ideals and expectations, and (3) relationship rules for condom use. Our findings indicate that young African American MSM rely on previous relationship experiences and desires for romantic relationships to determine condom use in subsequent relationships. Participants revealed that their previous relationship experiences and desires are often in conflict with their descriptions of their ideal romantic relationships and subsequently influence their condom use. Our findings fill a gap in the literature describing male-male romantic relationships and condom use among young African American MSM.