Empathy is a fundamental value in medicine and medical education and is often regarded as an antidote to the widespread perception of dehumanization in contemporary clinical practice. However, the concept of empathy—along with related notions such as attention—remains ambiguously defined and inconsistently theorised. Current approaches tend to emphasise the understanding and measurement of empathy primarily for remedial or instrumental purposes. This article challenges dominant discourses on empathy in medical education by arguing that the privileging of competencies fosters a reductive and overly instrumental approach to its teaching and learning. Drawing on literary narratives, particularly Gabriel Weston’s Dirty Work, Wilfred Owen’s poetry, and classical texts such as Homer’s Iliad, the study proposes that the ancient concept of ‘pity’ provides a richer and more integrated framework for understanding interpersonal care. Situating empathy within broader debates on narrative medicine, professionalism, virtue ethics, and aesthetics, the article reconceptualises medical communication not merely as a measurable competency but as a form of embodied virtuosity. Ultimately, it calls for an educational paradigm shift—from the quantification of empathy toward the cultivation of ethical responsiveness through narrative engagement, touch, vulnerability, and the aesthetic formation of the medical self.