PRWORA attempts to limit welfare use and encourage self-sufficiency in families headed by unmarried parents by promoting the goal of marriage. This paper addresses some important issues that underlie policy discussions of encouraging marriage and strengthening fragile families. In particular, the paper analyzes data from the first seven cites of the Fragile Families and Child Wellbeing Survey to investigate how economic factors, cultural and gender beliefs, and relationship characteristics shape unmarried mothers' and fathers' expectations about marrying their child's other parent. The results show that unmarried parents, and cohabiting parents in particular, have high hopes about marriage at the time of their child's birth. The analysis also finds that reporting drug or alcohol problems, frequent conflict, physical violence, and gender distrust are associated with lower marriage expectations, while perceiving benefits to marriage and living with the other parent are associated with higher expectations. Mothers with employed partners also hold higher expectations for marriage before controlling for cohabitation. For parents who desire marriage, it might be possible to support them in this transition, particularly through policies that help families overcome economic and structural barriers to their stability. At the same time, it is important to recognize the reasons unmarried parents have low expectations about marriage, such as drug or alcohol problems, conflict, distrust, and perceiving little benefit to marriage. Encourage marriage for parents in these circumstances might not only be inappropriate but detrimental to families.