The OED distinguishes two principal senses of the word “conversation”: “the action of living or having one’s being in a place or among persons”, and “interchange of words, thoughts”. The first (indicating a kind of habitus, frequently with moral inflection) presumes more about a conversant than the second. Hence in Pericles Gower speaks of the hero as “the good in conversation”. While there is some overlap, there is a significant gap in meaning and a kind of cultural struggle waged between the two. In the early modern period the first sense (deriving from Augustine and the Theatrum Mundi) might be thought of as dominant and the second emergent. Both were the focus of theoretical elaboration: the first principally by puritans (resulting in a register of “Christian conversation”), the second in two principle ways, by Steffano Guazzo and Montaigne. Guazzo’s Civile Conversation (tr.1581, 1586) begins by conceding its profanity in Augustinian terms, but then proceeds to redefine the word in a secular, pragmatic and essentially modern sense. Montaigne’s understanding of conversation is informed by Guazzo’s but adds a sophisticated understanding of conversation as dialectic. What I propose is to sketch these various meanings of the word “conversation”, speak to the “turn” from one end of its spectrum of meanings to the other, and then identify this spectrum of meanings in Shakespeare. That Shakespeare understands conversation in its pragmatic sense should come as no surprise, but that he should systematically understand it in the sense of a moral habitus while also exploring it in the sense of dialectic should surprise.