Understanding the determinants of marital timing is critical because it has implications for marital functioning and divorce. One salient predictor of marital timing is youth’s desires for marriage timing. To shine light on predictors of both desires for marital timing and the timing of marriage itself, we examine offspring marital desires and maternal marriage characteristics in the National Longitudinal Survey of Youth, 1979 (NLSY79) cohort and 1979 Child and Young Adult cohort (NLSY79-CYA; biological offspring of the women in the 1979 cohort). Analyses showed that maternal cohabitation postdivorce predicted decreased expectations to ever marry in offspring. Maternal age at marriage was positively associated with offspring desires for age at marriage, but only for those whose mothers had not divorced. Maternal marital age was significantly associated with the offspring’s transition into marriage even when controlling for the offspring’s desires for marriage timing, but neither maternal marriage age nor offspring desires for marital timing were associated with the timing of entrance into cohabitation, whereas maternal divorce was associated with earlier cohabitation. Our findings suggest that maternal marriage characteristics, particularly divorce, are significant predictors of millennials’ desires for and experiences with romantic relationships.