This thesis examines Charles Taylor’s concept of “cross-pressure” as illustrated in Flannery O’Connor’s two novels, Wise Blood and The Violent Bear It Away. Taylor argues that ever since the emergence of “exclusive humanism” humanity has been forced to inhabit an “open space” in which the “cross-pressure” of world views has characterized its experience and rendered any form of “naïve faith” impossible. This thesis will illustrate how O’Connor’s novels reflect this “open space” and the “cross-pressure” with which it is assailed, subjecting characters and reader alike to a fundamental ambiguity concerning the structure of reality. Accordingly, it will argue against the situating of O’Connor’s work strictly within the limits of grotesque realism and in favor of situating it on the border of the grotesque and the fantastic, this latter being characterized as obliging the reader “to hesitate between a natural and supernatural explanation of the events described”.