This dissertation explores Middle English literary texts that consistently portray ethics as a patently emotional affair. The introduction rehashes recent neuroscientific discourses that similarly assert the centrality of emotion in processes of ethical decision-making, as well as other contemporary theoretical and historiographic accounts of emotion. Chapter 1 argues that Middle English rhetorics of righteous and sinful anger played an important role both in sparking the Peasants’ Revolt of 1381 and in retroactively reevaluating the dangers of unin-hibited anger in the uprising’s posttramatic wake. The second chapter discusses Middle English discourses on dread that suggest that devotees in late medieval England conceptualized the ascetic project of dreading well as integral to the ethical project of living well. The third chapter argues that the three successive versions of _Piers Plowman_, as we know them today, contain three strikingly different theologies of love and dread. Rather than reading these as evidence of one man’s gradual movement from a theology of dread to one of love, it reimagines the production of _Piers Plowman_ as a densely intersubjective affair that engendered a network of differing (and deferring) theologies of love and dread. Chapter 4 turns to the famous Middle English elegy _Pearl_, arguing that the Pearl-maiden does not prompt the dreamer to happily share in her celestial estate, but instead stirs his envy of her heavenly bliss, suggesting that terrestrial devotees ought to work through, rather than eschew, their envy of their celestial loved ones. Chapter 5 focuses on another poem solely attested in Cotton Nero A.x: _Sir Gawain and the Green Knight_. While critics often read Gawain’s shame at the end of the poem as sundering him from his fellow courtiers, I read Gawain’s shameful confession to the court as profoundly and successfully reparative of the homosocial, chivalric habitus wounded by Gawain’s life loving transgression. Moving next to Geoffrey Chaucer’s _Troilus and Criseyde_, Chapter 6 builds on a scholarly tradition that reads Troilus as a masochistic courtly lover, arguing that, at the poem’s conclusion, Troilus spontaneously transforms into a sadistic courtly hater. Since masochistic courtly love and sadistic courtly hate constitute different responses to social privilege, the courtly lover always already possesses the potential to morph suddenly into a courtly hater, as does Chaucer’s Troilus when he channels his disappointment at having lost Criseyde’s love into vengeful, militarized violence against any and all Greeks. Finally, by way of conclusion, I discuss some of the pedagogical implications of my research into Middle English ideologies of emotion, focusing particularly on the vexed question of how one might ethically teach medieval cultures of compassion.