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The division of household labor has long been a central lens for understanding everyday gender inequality, marital quality, and women’s well-being. This study examines how women’s premarital life experience influences their household division of labor after marriage. Much of the relevant literature examines post-marriage factors, obscuring the path-dependent nature of gender roles, and when unequal arrangements take shape. This question is increasingly significant in the context of contemporary demographic transformation: delayed marriage lengthens the premarital life stage, while shifting macro-structural and normative conditions reshape how families form and organize everyday life at the start of marriage. Accordingly, this study focuses on the transition to first marriage and asks (1) whether and how women’s premarital labor-market attachment and living arrangements shape the domestic division of labor in early marriage, and (2) whether these premarital “carryover effects” are amplified or constrained by regional male marriage squeeze. Specifically, by focusing on the prolonged and increasingly heterogeneous premarital life stage in China, this study wonders whether habits of autonomy cultivated before marriage can persist once couples enter the powerful, normatively structured institution of marriage. Using longitudinal data from the China Family Panel Studies (CFPS), linked to province-level marriage-squeeze measures constructed from census data, I estimate models that distinguish within- from between-province variation and test moderation via cross-level interactions. This paper contributes by reframing the domestic division of labor in early marriage as a life-course process, and by offering a more holistic account of the determinants of housework allocation. In doing so, it also clarifies how macro-level demographic trends, such as delayed marriage and fertility decline, can be read in reverse, through the micro-organization of everyday family life. It further integrates macro demographic pressures with micro-level household dynamics to explain why similar premarital trajectories can yield different gendered outcomes across regional contexts.