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Marriage has become increasingly complex with the rise of cohabiting unions across countries. We focus here on the implications of the romantic relationship biography over the early life course on health and well-being in later life. We examine the partnership by how the sequence, duration, and timing of the single, cohabiting, and marital status matter for health and the diverging consequences by culture and religiosity. Drawing on comparative data from the United States, Spain, and Italy, this study uses sequence analysis to capture the complexity of individuals’ romantic union histories from adolescence to midlife, followed by regression models that link these trajectories to later-life health. We further test how and when unions form, persist, or dissolve at different earlier life course stages, influencing cognitive, psychological, and physiological health outcomes in later life across countries. We place particular emphasis on the distinct religious and cultural contexts in Southern Europe versus the United States, illustrating how variations in religiosity shape normality around cohabitation and marriage. By analyzing the order, duration, and timing of cohabiting and marital unions, we provide new insight into how structural and cultural factors intersect in defining normality in romantic relationships with diverging implications on well-being.