Medieval penitential writings often proclaim envy to be the “worst” sin because it is committed without pleasure. Envy thus poses a problem for traditional moral frameworks that suggest sin can be avoided by turning one’s desire away from earthly pleasures — envious desire is not addressed by this solution. Unlike the other “deadly” sins, envy’s economy of pleasure and pain is not object-oriented, but other-oriented. This essay examines John Gower’s Confessio Amantis, arguing that its focus on envy inspires a reorientation of penitential morality around the pains and pleasures inherent in one’s relationship to one’s neighbor. Gower’s tales explore the proximity of envy and compassion, asking crucial questions about how envious identification can be turned instead into compassionate likeness, and commenting on the larger project of exemplarity and mimetic narrative.