This essay discusses critical approaches to culture, difference, and empathy in health care education through a reading of Junot Diaz’s “Wildwood” chapter from the 2007 novel The Brief Wondrous Life of Oscar Wao. I begin with an analysis of the way that Diaz’s narrative invites readers to imagine and explore the experiences of others with subtlety and complexity. My reading of “Wildwood” illuminates its double-edged injunction to try to imagine another’s perspective while recognizing the limits to—or even the impossibility of—that (...) exercise. I draw on post-colonial theory and feminist science studies to illuminate a text that is created and interpreted in a post-colonial context—the Dominican diaspora in the United States. The essay offers a model of historical and critical analysis that health care educators can use to frame the concept of empathy in the classroom and the clinic. (shrink)