While the literature on male sex work has increased significantly over the past decade, few studies examine the influence of relational dynamics in the lives of those engaged in male sex work. This qualitative study, conducted with a sample of male street sex workers in Sydney, Australia, explores how relationships color their involvement with sex work. The findings reveal the complexity of their relationships and how their interactions with others shape their engagement in sex work. The data also offer insight into how exit pathways are influenced by money and relationships that occur within this particular male sex work setting. Implications for health policy and intervention are considered.