This study extends previous research on safer sexual behavioral practices by exploring the relationship between self-esteem and risky sexual behavioral practices. The Health Belief Model is the theoretical model used in this research. The Health Belief Model has been used to predict preventive health behaviors (Weiss & Lonnquist, 1993). To test the model, a questionnaire was given to undergraduate Introductory Sociology students at a land-grant university. What this research found, was that self-esteem was statistically significantly related to risky behaviors; more specifically, for those sexual behavioral practices which carry the highest risk, such as unprotected anal intercourse and sharing of needles for the injection of drugs. Students with high levels of self-esteem, as well as high levels of knowledge of HIV/AIDS, reported engaging in safer behavioral practices, for the unconventional sexual behaviors than those with low and moderate levels of self-esteem. With respect to those more conventional sexual behavioral practices, such as unprotected vaginal/penile intercourse and unprotected sex with multiple sex partners, those with high self-esteem reported more risky sexual behaviors than those with low and moderate self esteem which was not as hypothesized. Males and females reported similar levels of unconventional risky sexual behavioral practices and conventional risky sexual behavioral practices. The results indicate that self-esteem operates differently in different contexts. An important result of this study is that factors which predict unconventional sexual behavioral practices are not the sa,me as those which predict conventional sexual behavioral practices. Theses differences need to be taken into account by those trying to influence less risky sexual behavioral practices.