Claims about literature’s capacity to cultivate empathy have become commonplace across literary studies, narrative medicine, healthcare education, and the medical humanities. Yet the concept itself remains surprisingly difficult: variously understood as a cognitive skill, an affective response, a moral disposition, a professional competency, or a culturally specific mode of relating to others. At the same time, the relationship between reading and empathy continues to generate debate. What, precisely, happens when a reader encounters a literary text? How does this compare to what occurs when a clinician encounters a patient? What forms of attention, interpretation, and understanding are at stake in each case? This online symposium brings together researchers, practitioners and early-career scholars working at the intersection of literary studies, medical humanities, healthcare, and related disciplines to think about what literary approaches and contemporary clinical practice have to say to one another. We take as our starting point the conviction that empathy is a genuinely difficult concept, one which seems well-worn and yet remains contested and culturally specific. Rather than assuming empathy as a straightforward good or measurable outcome, we invite participants to explore its ambiguities, limits, and possibilities.