Vincent Lam’s Bloodletting and Miraculous Cures opens with an epigraph from the late-nineteenth-century Canadian medical pioneer William Osler (1849–1919): “medicine is a science of uncertainty and an art of probability.” For Osler, each patient had a story to tell, and the doctor’s job was to decipher, interpret, and act upon the information gathered, as uncertain as such a process might be. To supplement the notion of “narrative competence,” this article considers the conditional relationships between narrative medicine, bioethics, and fiction. It turns to the patient-centred novels of Kathleen Winter (Annabel) and Emma Donoghue (Room) before returning to Lam’s stories about physicians (in training and after) in Bloodletting and Miraculous Cures. “What if” stories like these illustrate both the strengths and the weaknesses of the medical system as they imagine the impact of medical decisions on characters over long periods of time and in great detail. This article investigates how stories that highlight the constraints of medicine and the problems of health care might augment medical pedagogy, particularly the introduction of bioethical debates. Along the way, the article argues that fiction can trouble two of the core elements that seem to be at the base of narrative medicine — the doctor as good listener model and the decipherable patient model. From both ends of the stethoscope, the stories that we read in these three texts about health care, sexualized violence, medical standardization, and problems in doctor-patient relationships elicit important dialogues about ethical dilemmas in health care and contemporary culture.