Ancient Romans had a great sense of irony, in theory and in practice. They used it abundantly and discussed what it is, what it achieves, and how it works and relates to other figures of rhetoric. And yet, their practice of irony seems to stretch beyond these theories. In this presentation I have two main arguments: pragmatics help to make sense of various instances of irony in Roman life and Latin literature better than ancient theories and definitions do; but ancient Romans anticipated some discoveries brought about by pragmatics.