Background: Previous studies identify consistent patterns of economically disadvantaged backgrounds, educational deficits, and relatively weak labor market outcomes of teen parents. Objective: In this study, we provide an updated report on differences in adult cohabitation rates during past decades, examine the risk factors associated with becoming a teen parent, and track teen parents' educational and labor market outcomes until the age of 29 to examine whether the outcomes associated with become teen parents have changed in recent decades. Methods: We select two nationally representative birth cohorts in the National Longitudinal Survey of Youth (NLSY) 1979 and 1997 (N = 9821). We use the difference-in-difference approach to examine whether the positions of teen parents have progressed or worsened across the two cohorts. Conclusion: The birth rates to teenage girls remained unchanged across the two cohorts, but the reported rates of teenage fatherhood increased. The proportions of both unmarried teenage fathers and mothers increased between the two cohorts. Teen fathers and mothers came increasingly from single-mother families with disadvantaged backgrounds. The proportion of teen mothers or fathers living with partners has not changed, but there has been a major shift from marriage to non-marital cohabitation. The education and earnings of the 1997 cohort of teen parents showed some progress relative to the earlier teen parent cohort, but no progress relative to peers who were not teen parents.