This chapter illustrates how queer young adult literature might provide more nuanced versions of risk than the limited yet pervasive narrative of “at-risk.” Mason challenges the idea that “risk,” when associated with queer youth, necessarily entails harm and violence; he considers instead the pleasurable risks offered by queerness. This chapter rethinks the assumed constitution of risk by asking: at-risk of what? What does it mean for queer youth to actively “risk” (as a verb) versus being labelled as “at-risk”? Mason’s alternate version of risk emerges from Isabelle Holland’s 1972 novel The Man Without a Face, which is often censured by contemporary critics for its ostensibly outdated and problematic content, including an intimate teacher/student relationship. Drawing on Deborah Britzman, Mason argues that this relationship offers a model of queer pedagogy that illuminates the productive and pleasurable aspects of risk, including risk’s potential for altering our approaches to sexuality and relationality.