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People implicitly and explicitly construct and perform gender every day, increasingly via technology. Using sugar dating as a case study, this study investigates how sugar workers strategically construct and perform gender through technology in “sugar dating”. Through in-depth interviews with twenty-eight sugar babies in the United States, I find that sugar workers use technology for gender play. In fact, it is not just gender that sugar workers do in and through technologically mediated work, but rather through technology, they constantly construct and reconstruct their work personas intersectionally. To explain this dynamic, I developed the concept of “iterative technological affordance” (ITA), which, for sugar workers, is a fundamentally intersectional engagement with gender and its continuous, evolving presentation through their online profiles and interactions. Thus, though on the surface sugar babies may seem to reify gender norms—and in many ways they do—this research shows that they also disrupt gender norms.