This article looks at the intergenerational effects of family structure on family formation and economic dependency. Three explanations are examined: thee conomic-deprivation, socialization, and family-stress hypotheses. Daughters living in single parent families at some point during adolescence are more likely to be come household heads and to go on welfare than offspring of two-parent families. Differences in the incomes of one- and two-parent families can account for up to 25 percent of the difference in offspring behaviors. None of the hypotheses, however, provides a complete explanation of family structure effects. The analysis is based on data from the Panel Study of Income Dynamics and uses event-history analysis to estimate transitions into female headship and economic dependence.