This article interlaces the story 'Comfort' by Alice Munro with Hannah Arendt's understanding of education as intergenerational passing on. Its principal aim is not to criticise Arendt or the fictional character of Lewis but to work with them towards a richer and more complex understanding of what can go wrong in education in general and teaching in particular. For this purpose, the article does not start from a theoretical framework but from the concrete aesthetic artifact -- the story -- itself. The departing question is: What can we learn from the literary description for our theoretical understanding of the intergenerational in educational relations?