This article traces the recurrence of certain “obstacles” in the work of Paul de Man. My analysis centers on de Man’s essays on Romanticism in order to locate what he describes as a “shift” from “historical reflection” to the “problematics of reading.” De Man’s renewed attempts to describe this shift—and to name the obstacle that occasions it—draw on the very same language he uses in his reading of romantic texts. Focusing on de Man’s reading of Baudelaire and Hölderlin, in particular, I examine the obstacles de Man identifies within the work of these authors, as well as the ways these obstacles disappear and resurface in later essays. Although I maintain de Man never succeeds in actually naming this obstacle, his repeated attempts to confront it attest to the importance—perhaps even the necessity—of stumbling as a constitutive feature of his critical project.