Our study entails a quantitative analysis of the life courses of permanent celibates in Dutch cities. We make use of a large database with randomly selected life courses (Historical Sample of the Netherlands), which covers the entire country in the second half of the nineteenth and the first half of the twentieth century. The database allows us to look at the family backgrounds, households, and mortality of urban singles. Singles were characterized by a prolonged stay in the parental house, which was related to the survival of both parents. Becoming single was more likely in Roman Catholic and elite families. In cities, skewed marriage markets contributed to women remaining unmarried. However, the well-known concentration of lifelong spinsters in cities was mainly caused by the clustering of social groups in which female celibacy was more common than in others, as well as by sex-specific migration to cities. Although they lived with their parents well past adolescence, in later life, urban celibate men and women did not depend on family. Women lived in a same-sex household more often than men. In old age, most celibates lived by themselves, but their “solitude” did not necessarily imply they were doing worse than others; at least, it was not reflected in higher mortality rates.