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Addressing a significant indicator of the “demographic crisis,” past studies have identified important factors motivating the retreat from marriage. We build on this scholarship by further clarifying specific mechanisms that limit the transition to first marriage. We first explore qualitative data derived from 40 in-depth interviews to identify the gendered pathways to singlehood in South Korea. Inductive analysis of interview data highlights the anxieties surrounding the economic costs of forming and maintaining families. Upon closer assessment, this burden is manifest differently for men and women based on Korea’s gendered marriage culture: providing housing upon marriage is a salient concern for men while the challenges of maintaining a healthy work-life balance is important for women. We then test these ideas using longitudinal data from the Korean Labor and Income Panel Study (1998-2017). Survival analysis of the KLIPS dataset confirm important differences between men and women. Parental wealth, an important precondition for home purchases, is positively associated with men’s chances of marriage but not significant for women. Human capital investments related to launching and sustaining careers, on the other hand, significantly discourage women's marriage outcomes but increase the odds for men. In a cultural context where marriage and parenthood are tightly coupled, our findings have implications for related aspects of demographic change, including “lowest-low” fertility, “super-aging” societies, and the rise of never-married single-person households.