Teen mothers as a cohort are disproportionately disadvantaged before pregnancy and are assumed to be further disadvantaged by an early pregnancy. A growing number of studies report that teen mothers and their children are disadvantaged slightly, if at all, by young maternal age. These studies highlight the social determinants of early childbearing but do not reveal the social contexts that shape the transition into adulthood for teen mothers' offspring. This report addresses this gap by presenting two cases from a longitudinal study that investigated how family members' lives unfold in the context of race, class, family practices, and communities. By the sixth wave, two of the mothers' first-born children had become teen parents. Both cases showcase the diverse outcomes and cumulative impact of social advantage and disadvantage on the transition into young adulthood. Implications are described in relation to what is known about social inequities in the transition into adulthood.