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Quantitative studies of gay and bisexual men have often reduced relational experiences to single dimensions and explored linkages with sexual risk behaviours. We sought to document the intersection of multiple relationship dimensions among 218 HIV-positive and 556 HIV-negative gay and bisexual men, and estimate associations with love and affection as well as various health and social covariates. We performed latent class analysis of relationships, employing five indicators: relationship status, sexual agreement (monogamous/open), and number of recent sex partners, sex parties, and anonymous sex encounters. We assessed differences in love and affection, and identified covariates using multinomial logistic regression. Two latent classes involved single men: 'single, less sex partners' (45% of sample) and 'single, more sex partners' (17%), differentiated by number of partners (52% vs. 92% of each class had ≥5 partners, respectively), party sex (3% vs. 57%), and anonymous sex (2% vs. 58%). Three involved regular partners: 'monogamish' (15%) (78% were monogamous yet 50% reported ≥1 recent sex partner); 'open, less sex partners' (15%) (100% open, 43% ≥5 partners, 10% party sex, 4% anonymous sex); and 'open, more sex partners' (9%) (96% open, 92% ≥5 partners, 47% party sex, 69% anonymous sex). Love and affection were common across classes, although more prevalent among partnered (85–91%) versus single (48–51%) men. Relative to 'single/less partners,' the study demonstrated that higher sexual sensation seeking scores were associated with membership in every class except 'monogamish'; erectile dysfunction drug use was associated with being in the 'more partners' (single and open) classes; anxiety and older age were associated with the 'open/less partners' class; and loneliness was associated with reduced odds of membership in all three partnered classes. We uncovered considerable relational diversity among gay and bisexual men and complex associations with love and wellbeing. Findings are relevant for sex researchers, educators, and therapists.