This study represents a comparison between two radical gestures of literary selfreflexivity romantic irony and postmodernist metafiction. It examines the impact of early German romantic theory and its central concept of irony on German and English romantic narrative fiction and relates the same to postmodernist selfreflexive novels including its British and American variants. A primary objective of this comparison is to account for the radical skepticism that postmodernist metafiction voices with respect to the paramount philosophical question of truth and reality. The immanent tension between an absolute idealistic and a radically skeptic position which romantic irony articulates and enacts is conceived of as an important and instructive link to the understanding of postmodernism.