The article offers poetry criticism of the poem "Troilus and Criseyde," by Geoffrey Chaucer. It offers an analysis of the similarities between Chaucer and Guido Cavalcanti and their beliefs toward love. It examines the character Troilus' pessimism on love, and how it differs from Boccaccio's Troiolo in Filostrato. The possibility that Chaucer knew Cavalcanti's work is discussed.