While concerns have been raised about declining marriage and fertility rates and increasing union dissolution, less attention has been paid to individuals remaining single. We ask whether individuals with different occupational characteristics experience different chances of remaining single throughout their lives and whether this relationship has changed across birth cohorts for men or women. We focus on Italy, a familistic context where exacerbated work-family conflict may hinder family formation for career-oriented women, while the male breadwinner norm makes occupational outcomes crucial for men's mating market chances. Based on Kaplan-Meier survival curves and logistic regression models using rich retrospective survey data, our analysis suggests that stronger labour market attachment is positively associated with singlehood for women and negatively for men. The work-family trade-off appears to have disappeared for women across the birth cohorts studied, whereas careers have become increasingly relevant for men, suggesting that the male breadwinner model is strongly entrenched in Italy.