The social and artistic implications of compassionate identification with suffering are ubiquitous in Geoffrey Chaucer’s writing, with feminized ‘erotic pity,’ compassionate governance, and narratorial sympathy with his characters often overlapping to generate social benefit and artistic invention. Despite this apparent endorsement of compassion—particularly feminine compassion—characters like Antigone and Cassandre in Troilus and Crisyede markedly reject identification and sympathy with male characters’ suffering in their efforts to create, perform, and comment on literary productions. Marking places where Chaucer himself wrestles with his source material, Antigone and Cassandre’s participation in poetic and historical authorship suggests the potential productivity of less conventional and more feminine-coded “affects of invention” (to borrow Steele Nowlin’s term)—envy, arrogance, impatience—in emulating and revising literary authorities. This feminine authorial position is delimited, however, by the unequal treatment of male and female emotion, both by characters and by Chaucer himself. Antigone and Cassandre, among other female creators, are ultimately marginalized or sanitized to avoid acknowledging this inequality. Exploring the potential and limitations of these characters’ non-compassionate authorship, this paper argues that Chaucer exploits the possibilities of negative authorial affect without resolving the discomfiting discrepancies between how male and female ‘ugly feelings’ are treated.