Drawing on 150 in-depth interviews with African American male and female youth who have spent much of their lives in neighborhoods of concentrated poverty, we explore the structural and cultural underpinnings of the elevated rate of unplanned childbearing among disadvantaged youth. We find that gender asymmetry in perceived opportunity costs, shared social meanings associated with condom use, and perceptions of health risk associated with hormonal and other female forms of birth control such as intrauterine devices—perceptions that may be rooted in a generalized distrust of the medical establishment—are promising explanations not usually considered in the literature on unintended fertility. These findings offer additional insight into how disadvantaged youth calculate the opportunity costs of childbearing and raise additional considerations for policies surrounding family planning and reproduction in the context of urban poverty.