This study focuses on the allocation of household labor in Italy, finely differentiating between various forms of married and unmarried cohabiting unions. Specifically, currently married and cohabiting individuals are differentiated on the basis of the type of their first union. We employ data on individuals’ partnership histories from the 2016 “Families and Social Subjects” survey, which allows us to consider the role of previous (marital or non-marital) unions and, for currently or previously married individuals, whether or not they cohabited before marriage. A composite index measuring gender equality in household labor allocation is constructed based on different domestic tasks, weighting each task according to how time consuming the associated activity is. Results highlight the importance of considering the first union to explain the division of household labor even within later relationships. In particular, for men, cohabitation does not, as one might expect, mean a more egalitarian division of labor, once selection factors are taken into account and independently from the type of previous relationships. However, considering activities by gender, some signals of a greater participation in female-typed tasks are observed for married and cohabitating men who experienced previous (premarital) cohabitations. For women, instead, cohabitation implies a more egalitarian way to share household labor, if it is a first union or in any situation for which it was the first approach to life as a couple. Cohabitation does not imply a more egalitarian division of labor for women if their first union was a marriage. These differences in household labor allocation for women mainly follow from those observed in female-typed tasks, whereas couple differences in male-typed activities are weaker.