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This paper examines the conversational exchanges depicted in Cicero’s De Oratore and considers what they may tell us about linguistic politeness in Late Republican Rome. It focuses in particular on verbal expressions of modesty, which have been identified as a prominent feature of interactional pragmatics across various different cultures. (See e.g. the “modesty maxim” proposed by Geoffrey Leech in Principles of Pragmatics (1983) and The Pragmatics of Politeness (2014).) We shall see that (1): Cicero’s interlocutors deploy a range of linguistic strategies of self-effacement; (2) this avoidance of self-praise is often linked with the desire to avoid the invidia of onlookers; (3) these polite expressions of modesty were a semi-conventionalized feature of elite manners that could on occasion be manipulated for witty ironic effect; and (4) praising others face-to-face could also prove to be a delicate social maneuver. Overall, Cicero’s fictional dialogue presents an idealized, yet generally credible depiction of sophisticated aristocratic politeness.