In this study, we used a mixed methods approach to explore the determinants of relationship patterns and risky sex among homeless men living in downtown Los Angeles. This involved analysis of qualitative interviews focused on gender ideology and sexual events (n = 30) as well as structured interviews (n = 305) focused on homeless men’s sexual partners, sexual behaviors, and social networks. We found that men valued committed relationships but were frustrated by their lack of access to female partners (accentuated by the stigma attached to homeless males) and also by structural and logistical barriers to relationships. Some men reported monogamous relationships; such relationships were less likely with homeless or substance-using partners and more likely with partners central to men’s social networks.