The aim of this study is to examine whether or not self-esteem, demographic factors and being in prison influence a person’s dependency and involvement in prostitution. There are five hypotheses at work based on these aims. This study will be carried out on an all-female prison and all-female non-prison sample. All participants filled out the Addiction Severity Index, the Rosenberg Self-Esteem Questionnaire and the Leeds Dependency Questionnaire. A significant relationship was found for hypotheses one and no significant relationship was found for hypotheses two and three. Hypotheses four and five could not be evaluated as only a prison sample was available. Although only one significant result was found, the descriptive statistics and standardized beta weights from the regression analysis give an interesting look at the scores accumulated and how they relate to previous research. Future research conducted should look at the interaction of specific demographic factors such as medical issues with dependency and involvement in prostitution on the basis of results obtained from this research piece.