This project is concerned with the life courses of women who were arrested in Bruges during the second half of the eighteenth century (1750-1790) because they were working as prostitutes. In the study we describe the constraints on a prostitute’s life as well as the prostitute’s capacity to act within those constraints. In addition, this project provides us with information regarding the organisation of prostitution in a small urban setting and how the authorities policed it. By using a life course analysis, we were able to analyse both the reasons for, and consequences of, prostitution. Correlating information from parish and civil registers of births, marriages and deaths enabled us to reconstruct the entire life course of many individual prostitutes, above and beyond the snapshot provided by court records at the time of their arrest. This methodology sheds new light on the idea of the ‘happy hooker’, as well as on the supposed marginal position of the prostitute within society, and the passive acceptance of her own fate. It shows that most prostitutes were ordinary local women, although they more often than others had lost one or both parents. It also shows that the majority of prostitutes worked in closed brothel houses, and therefore were dependent of brothel keepers. Still, the prostitutes’ hearings, in which their own words were recorded, show that not all such women felt constrained. They for instance indicated that they earned more money than they could elsewhere. Instances of enforcement are truly exceptional; however, it is clear that many women were persuaded by false promises, and some were entrapped by systems of bondage. Hence, this study is a thorough analysis of the complexities of prostitute life. It acknowledges the difficulties eighteenth century prostitutes faced, but also stresses their agency.