Young, homeless women often become pregnant, but little is known about how street youth experience their pregnancies. We documented 26 pregnancy outcomes among 13 homeless women (ages 18–26) and eight homeless men through interviews and participant-observation. Eight pregnancies were voluntarily terminated, three were miscarried, and fifteen were carried to term. Regardless of pregnancy outcome, street youths’ narratives focused on ambivalence about parenting, traumatic childhood experiences, and current challenges. Despite significant obstacles, almost all were convinced of their personal capacity to change their lives. While most wanted to be parents, the majority lost custody of their newborns and consequently associated contact with medical and social services with punitive outcomes. Most of the youth who chose to terminate successfully sought safe medical care. We offer recommendations for changing the approach of services to take full advantage of pregnancy as a potential catalyst event for change in this highly vulnerable and underserved population.