This is the story of one medical educator's attempt to combine literary and epistemological inquiry in a 4th-year elective called Women's Health: Views from Literature, Communities, and Clinical Medicine. The assumption fueling this attempt was that medical students' thinking rarely moves outside rationalist constructs, and because of this, they often confuse the nature or distinguishing features of something or someone-its quality-with what the numbers tell them. Thus, the class content and experiences were purposely developed to engage the students with knowledge from a variety of qualitative domains and would be, as such, an epistemological experience. This article details how the class worked and how it did not.