Globally, sexuality education is framed as a key programmatic strategy for achieving HIV prevention among youth. In particular, sexuality education is positioned as a way to address gender inequalities and promote youth empowerment in relation to gendered identities. In this paper, I argue that the focus on what content should be taught and "what" is the effectiveness of that content serves to mask how sexuality education itself is always a political project. Specifically, I problematise a neo-liberal "political rationality," following Wendy Brown, operating through sexuality education in this particular globalised moment. Drawing on data from an ethnographic study conducted in South Africa, I use the notion of encounters with gender to mobilise understanding of gender with(in) the inevitable risks of knowing and being known through educational research and practice. I argue that holding sexuality education responsible to the complexity of lived lives necessitates proposing alternative political rationalities to guide its encounters.