This mixed method study aimed to gather a contextual understanding of the perspectives of young girls in South Africa with regard to transactional sexual interactions between older men and young girls. Two major narratives of the “sugar daddy” phenomenon have dominated the public discourse on the topic. One emphasises the girls' vulnerability and experience of victimisation, whereas the other highlights their role as social agents with control in such interactions. In this study, the participants acknowledged the heterogeneity among partners in such interactions, which suggests that the phenomenon of “sugar daddies” cannot be explained by a simple narrative. The girls' experiences form a continuum based on the degree of their individual control and the extent of their vulnerability in such an interaction. Contextual factors and social norms influence decisions and experiences in these interactions. The study concludes that these relationships form part of the girls' daily experiences of structural violence as well as gender inequality and can be regarded as a symptom of broader societal structures and norms. Quantitative data investigate the mental health status of the participants, whereas an essentialist/realist thematic analysis of qualitative data explores experiences and perceptions of the girls.