Unintended pregnancy has conventionally been defined as a pregnancy that is mistimed or unwanted, and this classification has been widely used in survey research. This study explores the utility of these constructs for women who visited a family planning clinic and a prenatal clinic in inner-city New Orleans, LA, and, by extension, for women of similar background and experience. We used semi-structured, open-ended research to explore sexual debut and history, contraceptive knowledge and use, pregnancy history, partner relations, and service use among 77 women (73 of whom were African-American). This study addresses the apparent paradox of high-risk sexual and contraceptive behavior in the presence of expressed preferences to postpone childbearing. It provides some insight into the cultural and social context in which these events and decisions take place and explores the multiple dimensions that shape women's sexual behaviors and their desires for pregnancy. The dimensions explored include perceptions of and experiences with sex/sexuality, values concerning childbearing/motherhood, relationships with partners, experiences with contraception, and attitudes toward abortion. The apparent ambivalence seen in reports of women asked whether a pregnancy was intended, such as statements that they did not want to get pregnant but were either not using contraception or using it irregularly, calls into question the idea that intendedness can be routinely and easily inferred from survey research. Correspondingly, it is not possible to simply assume that either intentionality or future intentions directly affect decisions to use contraception. The problem is that the many factors-structural and individual-affect women's preferences and ability to postpone a pregnancy or to use contraception.