This study explored how single individuals navigate their relationship status through distinct psychological and behavioral patterns, with implications for applied psychological interventions. Using an exploratory latent profile analysis, we examined singlehood beliefs, relationship expectations, and sexual motives across two cross-sectional studies in the United States (Study 1, N = 499; Study 2, n = 274) and Portugal (n =221).Consistently across both cultural contexts, three profiles emerged. Involuntary single individuals feared singlehood, endorsed normative relationship beliefs, and reported more negative reasons for being single. They also engaged in condomless sex for external reasons and, despite prioritizing pleasure promotion in sex, reported lower sexual quality of life and well-being. Pleasure-driven voluntary singles were comfortable with singlehood, held some relationship expectations, and focused on personal enjoyment and pleasure promotion in sex. They reported higher sexual quality of life and well-being. Cautious voluntary singles prioritized disease prevention in sex, were the most committed to singlehood, and endorsed more positive reasons for being single. However, they reported lower sexual satisfaction and well-being. These findings highlight the diverse experiences of singlehood, shaped by internalized and socialized relationship norms. Understanding these profiles offers valuable insights for developing targeted interventions aimed at enhancing sexual and relational well-being among single individuals across different cultural contexts.