The term blesser has become part of South Africaâ??s contemporary lexicon, replacing the older terminology of â??sugar daddy.â?? While much recent literature has focused on the blesser phenomenon, the voices of orphaned adolescent girls on their entanglement in blesser relationships have had insufficient attention. Using the theory of gender and power as an analytical lens, this qualitative study analyses the visual and textual data generated by orphaned adolescent girls on their relationships with blessers. To generate data, the participants used photovoice to represent their relationships with older male sexual partners in their resource poor South African township neighborhoods. Our analysis reveals a set of factors that render orphaned adolescent girls vulnerable to age-disparate relationships, such as the structural dimensions of their lives, including their status as orphaned girls, heteropatriarchy, age-based hierarchies, and poverty in their households and communities. On the other hand, our analysis explores the less understood area of the relative agency, intentionality, and proactive approach that orphaned girls take to initiating and negotiating blesser relationships. The findings have implications for further research that will expand our understanding of girlsâ?? agencyâ??and the structural limits to that agencyâ??in adverse socio-cultural circumstances. Such research holds potential for interventions that might enable orphaned girls to better advocate for themselves in the context of unequal power relations.