This case study presents the use of propensity score matching for estimating the causal effects of teenage motherhood on personal transformation (i.e., self-worth, life satisfaction, and orientation toward risk, the future, and relationships). A great deal of research examines the effect of early motherhood on negative life outcomes, including educational deficits, unemployment, health problems, and drug use, yet few studies consider the potential positive outcomes of early motherhood typically expressed by teenage mothers, the focus of this case study. It describes the problem of selection effects and the use of multiple quasi-experimental methods that minimize the potential for selection bias in addressing the impact of early childbearing on social outcomes, including sister-comparison analyses and miscarriage/instrumental variable models. The case study uses nationally representative data from the National Longitudinal Study of Adolescent to Adult Health (Add Health), which is ideal for propensity score analysis, and it takes a step-by-step approach to explain how to conduct propensity score matching using Stata 14. Methodological choices regarding propensity score analysis, in general, and research on teenage motherhood, in particular, are discussed.