Irony and sarcasm are famously difficult. The ability to understand irony at all comes relatively late in cognitive development, and even adults frequently misinterpret it. As Wayne Booth observed in his classic book The Rhetoric of Irony, “even highly sophisticated readers often go astray” in navigating ironic discourse. Irony is also difficult to manage on the production side: people often overestimate how transparent they are in their sarcastic intentions, especially in writing. And irony is difficult to define, as well. Do dramatic irony, cosmic irony, Socratic irony, Romantic irony, and all the other things that have been described as varieties of “ironic” experience really have anything of substance in common? In this talk, I will discuss a somewhat less frequently explored sense in which irony is difficult, the fact that ironic stances are surprisingly difficult to maintain over time. I’ll tell the story of “irony attrition” — the erosion of ironic distance — as something that happens both to individuals and in discourse communities, including the case of “Sherlockians,” fans of the Sherlock Holmes stories who write scholarly articles, squibs, and entire books under the conceit that Holmes and Watson were real people (and sometimes that Sir Arthur Conan Doyle was a fictional one, as well). We’ll see how the difficulty of being ironic connects to larger patterns in both social cognition and language change.