Philosophical anthropologies that emphasise the role of the emotions can be used to expand existing notions of moral agency and learning in situations of great moral complexity. In this article we tell the story of one patient facing the tough decision of whether to be tested for Huntington’s disease or not. We then interpret her story from two different but compatible philosophical entry points: Aristotle’s conception of Greek tragedy and Karl Jaspers’ notion of Grenzsituationen (boundary situations). We continue by indicating some ways in which these two positions may be used for reflecting upon different perspectives involved in clinical decision-making, those of patients, clinicians and bioethicists. We conclude that the ideas we introduce can be used as hermeneutic tools for situating learning and dialogue within a broader cultural field in which literature and art may also play important roles.