Teaching and reading literature are commonly viewed as contributing to the cultivation of empathy. This article presents critical and pedagogical approaches to test this view and suggests a distinction between low-level, simple empathy inspired by the reading and teaching of "The Tortilla Curtain" and a more complex, self-critical understanding of empathy that acknowledges its reach and limits by reading and teaching "Half of a Yellow Sun." This distinction is observed in literary criticism and theory about teaching empathy, in the examination of teaching resources, and in the personal experience of teaching "Half of a Yellow Sun." The conclusion is that teachers and students should not be satisfied with simple or passive empathy, but rather can and should strive towards more critical and sceptical investigations of the power of the written word to educate towards empathy.