Thinkers such as Elaine Scarry and Kathlyn Conway have written about the problems of master narratives of illness: pain can mark the limits of what narrative can do. This essay argues that late medieval writers not only had an understanding of the impulse to fit illness into narrative structures but also understood the inherent limitation that emplotment and narrativization entails. Focusing on a doctor, John Arderne, a patient-poet, Thomas Hoccleve, and a poet, Geoffrey Chaucer, the essay explores how all three reveal their understanding of the artifice of narrativizing pain and illness. They present themselves as flawed and sick narrators, not as authoritative masters of the material of their texts. Surgeon and vernacular poet are connected by their social and cultural indeterminacy; they are vulnerable, feminized figures, aware of the contingency of their interpretations and the holes in their narratives. All focus on the limits of narrative and narrator alike, modeling the inability of narrative to make sense of pain.