This study examines the role that self-esteem plays in HIV-related risk taking among users of the drug, Ecstasy. The first part of the analysis focuses on the relationship of self-esteem to HIV risk-taking. The second part examines predictors of self-esteem in this population. Conducted between 2002 and 2004, the research is based on a sample of 283 young adult Ecstasy users who completed approximately two-hour-long, face-to-face interviews via computer-assisted structured interviews. Study participants were recruited in the Atlanta, Georgia metropolitan area using targeted sampling and ethnographic mapping. Results indicated that self-esteem is associated with a variety of risky practices, including: the number of sex partners that people had, individuals' likelihood of having multiple sex partners, the number of different illegal drugs people used, and their condom use self-efficacy. The multivariate analysis conducted to ascertain the factors that impact participants' levels of self-esteem yielded six factors: educational attainment (positive), coming from a family-of-origin whose members got along well (positive), the extent of alcohol problems (negative), the number of positive effects experienced as a result of Ecstasy use (positive), the number of negative effects experienced as a result of Ecstasy use (negative), and the extent of experiencing symptoms of post-traumatic stress disorder (negative).