This essay argues that an examination of Chaucer’s work reveals his indebtedness to the tradition of literary dialogue, understood as a work constructed in the form of an exchange between two or more persons, with characteristic concerns centred on questions of ethics, politics and religion. Critical to the form is its explicit engagement with different argumentative positions; a dialogue text may then, as in the Socratic tradition, leave the reader with a concluding aporia, or, as in Aquinas’ Summa, provide a resolution. After briefly reviewing the use of the dialogue form in classical and Late Antique writing, the essay goes on to explore the significant influence of dialogue in a number of Chaucer’s works, including The Book of the Duchess, The Parliament of Fowls and the Tale of Melibee, and argues that he is fully alive to the potentialities of the form for encouraging and indeed demanding readerly engagement.