Sexuality education as an HIV prevention strategy is positioned as a way to empower youth in relation to their sexual identities and behaviours. While the youth subject is recognized as complex, the underlying premise is that identity can be targeted "through" sexuality education. In this paper, I present data from an ethnographic research study, carried out with the South African non-governmental organization loveLife, that foregrounds identity as an ongoing site of struggle "within" sexuality education. Data are drawn from field notes, individual semi-structured interviews and artefact analysis. Bringing together the work of educational theorist Elizabeth Ellsworth and feminist geographer Doreen Massey, I theorize the pedagogical encounter as a momentary coming together of understandings of self and other across perceived spatial and temporal boundaries. The findings problematize the possibility of a stable (and "local") youth subject that can be targeted and empowered through sexuality education. At the same time, I argue that it is the impossibility of this project that might be a pedagogical resource for imagining social identities and their relations differently with youth.