In this chapter, the author provides a theoretical outline for a practice of rhetorical inquiry in the college writing classroom, and focuses on three conditions that permit this inquiry to enact a “pedagogy of discomfort” (Boler, 1999). The first condition calls for pedagogues to amplify the performative dimension of language to disrupt what Dewey terms the “quest for certainty.” Second, students and teachers work to reconfigure their current perspectives through undergoing dialogic encounters between incongruous perspectives. Third, these performative and dialogic encounters must reiterate with increasing complexity and within increasingly unfamiliar and complex contexts. After an extensive theoretical exposition of these three conditions for a disruptive pedagogy, I present a few illustrative instances in the college writing classroom.