Noting that both the earliest readers of Montaigne’s Essais and their modern counterparts have likened them to a dialogue with a friend, this article seeks to explore the work’s dialogic characteristics. The humanist dialogue is an obvious precursor to the Essais, and even though Montaigne voiced dissatisfaction with Plato’s dialogues, he aspired to match Plato’s style, not least in achieving a conversational tone. Three different elements of dialogue are analysed : the “Dialogue of One” between the different parts of Montaigne’s mind, the dialogue between the author and the writers quoted and paraphrased, and the use of direct address to the reader to invite or provoke the reader to enter into dialogue with the author. This essay is concerned to show how Montaigne uses the dialogue to create an entirely new genre, posed between monologue and dialogue.