Last year, guided by theories that regard sympathy as an imaginative capacity that can bridge divisions between people of different backgrounds, I conducted an experiment with nearly 200 Finnish secondary school students, in order to determine the extent to which particular texts would generate their sympathy for characters who seem unattractive, undesirable, or generally outside of the accepted norms of the societies in which they live. The present paper builds on my findings in that study by suggesting some of the pedagogical implications of providing adolescents with opportunities to engage with the lives of fictional characters, and particularly to experience feelings of sympathy for individuals toward whom they ordinarily might feel aversion or uncertainty. It examines some of the ways in which experiences with narrative fiction can be used to help develop emotional and conceptual structures in adolescent readers. In Education and Experience John Dewey contends that “the conditions found in present experience should be used as sources of problems”; indeed, the present paper shows how narrative experience can help form the basis for a problem-solving, emotionally-rich curriculum that takes as its primary aim the development of students’ capacities for emotional awareness and ethical reflection.