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Description: Singlehood in Western societies is becoming increasingly normative and acceptable over historical time. But whether these changes have contributed to higher satisfaction (singlehood satisfaction and life satisfaction) among singles is still unclear. In this preregistered study, we used data from a cohort-sequential longitudinal study including N = 3,161 participants (age at T1: M = 21.79, SD = 7.89; four cohorts born between 1971 and 2003) over a study period from 2008 to 2021. Results from multi-group structural equation models revealed that later-born adolescent singles were more often single and more satisfied with their singlehood than their earlier-born counterparts. No cohort-related differences emerged in older age groups. In addition, both satisfaction measures were highest among adolescents and singles who were more extraverted and less neurotic. However, intrapersonal factors did not moderate cohort-related differences in singles’ well-being. Together, the results highlight the importance of societal and intrapersonal factor for singles’ well-being.