Philip Roth has historically been situated in a male literary tradition, with critics assessing him alongside Saul Bellow, Bernard Malamud, and more recently, Charles Chesnutt and Ralph Ellison. Because of his problematic portrayals of women characters, Roth is not often discussed alongside women writers. My paper goes beyond this by situating Roth alongside a black woman writer, Nella Larsen. In fact, Larsen’s Passing (1929) and Roth’s The Human Stain (2000) share several thematic and structural similarities, such as the tropes of belated race learning, double consciousness, anonymous letter writing, taboo sexualities, and ambiguous deaths. My essay argues that these tropes underlie passing narratives and reveal the development of twentieth century passing texts.