This dissertation explores the use of romance across religious poetry in late medieval England. Medieval devotional poems frequently borrow motifs and devices from romance; they might, for example, figure Jesus as a knight jousting with the devil or adopt the romance technique of interlace to narrate the Passion. Critics most frequently read these borrowings as a popularizing method, arguing that the poets of these religious texts turn to romance in order to appeal to their secular audience. I argue instead that late 14th century Middle English poets use romance to explore difficult theological paradoxes and Christian practices. In Pearl, the romance descriptio personae helps articulate the paradoxes of divine reward, at once hierarchical and egalitarian. In Piers Plowman, the romance incognito demonstrates the shifting and multivalent nature of the Trinity. In St. Erkenwald, the slow indulgence of romance wonder stands in contrast to God’s time, which is simultaneously immediate and drawn-out. In the Canterbury Tales, the romance parody of Thopas primes the reader for the prudential lessons of Melibee. This dissertation adds to a growing body of scholarship that reads medieval romance, and in particular Middle English romance, as a genre that does not simply entertain audiences but also interrogates, challenges, or reiterates medieval values and ideas. However, this project adds to current scholarship by examining romance out of its native context and inside or beside religious genres instead. In the first three chapters, I argue that by triggering a romantic reading, the Middle English poems Pearl, Piers Plowman, and St. Erkenwald enact and demonstrate the conceptual difficulties of certain theological paradoxes. In these poems, romance serves as a contemplative tool by demonstrating the reader’s comprehensive limits in the face of the divine. My fourth chapter, which explores Chaucer’s romance parody Sir Thopas alongside his pedagogical treatise Melibee, instead considers the Christian virtue of prudence; here, the exaggerated romance tropes of Sir Thopas prepare the pilgrims to pay penance prudentially by feeling and contemplating time in daily Christian life. While romance does not articulate a paradox about God in Thopas-Melibee, it still prompts contemplation about a difficult Christian virtue, prudence. In all four chapters, I find that romance serves as a vehicle for spiritual contemplation because of its own modes of thinking, whether that be social, economic, or temporal. Whether romance is set within or beside devotional texts, the secular genre allows the reader to contemplate difficult Christian theology and practices and to experience them as difficult in contemplation. Romance, I argue, is a critical tool in the vernacular theologian’s toolkit.