Objective Drawing on the life course perspective and theoretical models of intergenerational solidarity, this research explores how adolescent-parent relationships (i.e., parent-child closeness, parental attentiveness, family routines, and parenting styles) are associated with young adults' transitions to adulthood. Background The study adds to the growing literature on adolescents' leaving and returning to the parental home by focusing on parent-child relationships and variations across gendered parent-child dyads. Method Based on data spanning nearly 2 decades from the National Longitudinal Survey of Youth 1997 (N = 5,201), event history analysis was employed to assess how intergenerational family dynamics correlate with young adults' risk of leaving (n = 4,519) and returning to (n = 2,749) the parental home. Results The results indicate that, net of individual, household, and other contextual factors, parent-child closeness is significantly and positively associated with leaving the parental home. This suggests that close parent-child relationships can help launch children into adulthood. Looking at returns to the parental home, closeness becomes significant for daughters only and is moderated by parent gender. In addition, measures of parenting style indicate a significant and negative association between more-passive styles and children's return to the parental home. Conclusion These findings highlight the need to more closely consider the impact of gender and parent-child relationship dynamics in facilitating young adults' transition to adulthood.