Regular male partners of female sex workers (FSWs) represent an important population to reach with HIV-prevention interventions. This paper discusses the relationship dynamics and HIV/sexually transmitted infection risk behaviour of men involved with self-identified FSWs in Kampala. Between 2011 and 2014 we conducted repeat in-depth interviews with 42 male partners of FSWs attending a clinic for women at high risk of HIV-infection in Kampala. Men publicly struggled with the stigma of dating women who are considered to be engaged in a shamed profession, but privately saw meaning in these relationships. In coping with the stigma, some described the work of their partners in terms that distanced them from sex work, while others struggled to have the control that "being a man" demanded since they could not monitor all movements of their partners. Dealing with HIV disclosure was hard and seeking support was difficult for some of the men, leading to missed opportunities and guilt. Despite challenges, relationships with sex workers offered men some benefits such as access to much needed care and treatment. A few men also admitted to being motivated by material and financial benefits from sex workers who they perceived as being rich and this was one factor that helped them sustain the relationships. These findings offer insights into the complex relationship dynamics within high risk sexual partnerships. However, the findings suggest that effective interventions that are couple centred can be established to promote better health.