In this study, we describe the relationship between self-esteem and HIV-related risk behaviors, and explore what factors predict self-esteem levels of "at risk" women. Interviews were conducted with 250 (predominantly African American) women living in the Atlanta, Georgia metropolitan area between August 1997 and August 2000. A community identification process was used to identify potential study participants, with further expansion of the sample via targeted and theoretical sampling and ethnographic mapping procedures. Self-esteem was related to the number of times having oral sex, the number of times having sex with paying partners, the frequency of sexual risk-taking (all during the 90 days prior to interview), the number of different HIV risk behaviors practiced during the previous year, and condom use attitudes and self-efficacy. Greater involvement HIV risk behaviors was associated with lower self-esteem. Multivariate analyses revealed five significant predictors of women's self-esteem levels: race, religiosity, childhood experiences with emotional neglect, the number of money-related problems experienced, and the number of drug-related problems experienced. The findings indicate that self-esteem is highly relevant to "at risk" women's HIV risk behavior practices, and this has important implications for HIV intervention programs. (c) 2004 by The Haworth Press, Inc. All rights reserved.