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Background: Research on diverging destinies of cohabitation and marriage tends to focus on singular transitions rather than entire individual trajectories composed of dimensions such as timing, order, duration, and number of transitions.

Method: Drawing on monthly prospective data from the National Longitudinal Survey of Youth 1997, social sequence analysis was used to classify union transition trajectories from ages 16 to 30. Multinomial logistic regression was used to assess the probability of membership in each cluster.

Results: The findings showed the following six key clusters of trajectories: mostly single (37.6%), some cohabiting (13.8%), serial cohabiting (10.6%), early 20s marriage (11.4%), late 20s marriage (22.5%), and turbulent (4.1%). We found that young adults were most likely to be in the "mostly single" cluster, regardless of socioeconomic status and race/ethnicity. Individuals with college degrees tended to marry in their late 20s, whereas individuals without college degrees were more likely to be in "serial cohabiting" and "turbulent" clusters. Individuals who lived with neither of their biological parents were more likely to belong to "early 20s marriage" and "turbulent" clusters when compared with those who lived with at least one of their biological parents. Blacks were more likely to remain single, whereas non‐Hispanic Whites were more likely to marry sometime in their 20s.