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In the penitential ethos of late fourteenth-century England, ideas about shame and guilt were of central concern. Preachers and poets, alike, considered questions such as: what role should shame have in contrition and penance? What is the precise relationship between physical purity and moral or spiritual purity? What are the emotions best suited to eliciting the fullest and most sincere confession? Such questions were posed explicitly in penitential manuals and handbooks, but they also formed the ethical and philosophical soil out of which many of the periods major literary works emerged. This dissertation examines representations of shame and guilt in the literary contexts and narrative poetry of Geoffrey Chaucer. I consider Chaucers treatment of these ideas in light of his contemporaries, especially the Gawain-poet, as well as a broader historical context, surveying shame and guilt in the Middle English literary traditions of romance and hagiography. I also explore recent developments in affect theory, and draw on work in anthropology and psychoanalysis in order to theorize the ethical dimensions of shame, guilt, and related ideas of agency and purity. I argue that much of Chaucers poetry, but especially the Canterbury Tales, articulate the private and public facets of these emotions, not only as matters for the confessional, but as representative of opposing ethical systems, and, therefore, as fundamental in shaping possibilities for human social life. I see Chaucer as a poet deeply concerned with ethical questions. His works consistently represent guilt as an ethical ideal whereas shame is often portrayed as the psychological reality that gets in the way of attempts to realize the ideal. From Dido to Criseyde to Virginia and Dorigen, many of Chaucers characters call attention to the injustice of guiltless shame: the way in which the individuals inner moral state conflicts with the external world of honour and shame. Thus, while Chaucers narratives present us with a full spectrum of ethical responses and psychological motives for evading or claiming moral responsibility, I pay special attention to the many ways in which shame is mobilized in service of social and gendered dynamics of power and victimization.