Ironic.

(Originally published, or rather Poasted, in another place, May 7, 2026.)

Umberto Eco speaks of a descriptive semantics and syntactics but a more ambiguous or dialectical descriptive-prescriptive pragmatics, and extols this as part of "a return to the very roots of the philosophy of language" (The Limits of Interpretation, p. 213). In that spirit, let's talk about the Alanis Morissette song "Ironic," which has been a subject of philological interest for almost my entire conscious life. (I have two memories that I think might predate Jagged Little Pill's release.) The song describes a number of vaguely, or more than vaguely, disappointing or frustrating situations, all of which it wants the listener to believe are ironic--yet only a few of them seem to fit the conventional definitions of irony used by humorists, dramatists, and so on.

"It's like meeting the man of my dreams, and then meeting his beautiful wife" is, for example, a perfect case of dramatic irony from the perspective of the man, and the verse taken up with the story of a man who overcomes his fear of flying only to die in a plane crash is also ironic in something close to a strict sense--what are the odds? "It's like rain on your wedding day," conversely, is not ironic and for that matter is not even universally agreed to be a bad thing. There has been considerable mockery of Morissette on this point over the years, which she acknowledges, describing herself in one interview as "the malapropism queen" ("Alanis Morissette's Jagged Little Pill at Thirty: Inside the Iconic 'Ironic,'" on the website "Music Musings & Such" by Sam Liddicott, as well as other sources).
Yet nowadays there are much looser usages of the term "ironic" that preserve some of the dark humor implied in the stricter meaning but have expanded enough to cover most--not all--of the situations in the song. In my copy of the 1965 edition of Fowler's Dictionary of Modern English Usage, the entry for IRONY takes up a whole page and is subdivided into three types--the third type, "the irony of Fate," covers the airplane verse--as well as a table under the entry for HUMOUR comparing and contrasting it with seven other terms. Fowler actively decries "the application of 'the irony of Fate', or of 'irony' for short, to every trivial oddity" (p. 306), which would seem to rule out most of the content of the song, all the more so given that he concludes that the irony of Fate, while a real form of irony, is also "to be classed now as a HACKNEYED PHRASE" (ibid.)! The descriptivist-leaning Merriam-Webster, on the other hand, now classifies "incongruity between the actual result of a sequence of events and the normal or expected result" as an acceptable secondary definition of the word, and points out that inexact usages such as Morissette's seem to go back at least a century anyway (which would explain why Morissettean usages were already hackneyed phrases by 1965). Even the much more prescriptive OED has "[a] state of affairs or an event that seems deliberately contrary to what was or might be expected; an outcome cruelly, humorously, or strangely at odds with assumptions or expectations" as a tertiary sense, without including any of Fowler's caveats about the usage's triteness. Again, this sense covers most of what is in the song, but not all.
The earliest citation in the OED that seems to exactly match Morissette's sense is from a book about fly fishing by a man named G.A.B. Dewar, published in 1897: "It is somewhat of an irony that Dry Fly fishing, which was primarily resorted to because it was the only sportsmanlike way of killing shy fish in clear streams, is now to be regarded as one of the things which help to make the trout more wary than ever." Isn't it ironic, don't you think?
A very recent usage might be Pope Leo's description of Truth Social. "It's ironic--the name of the site itself. Say no more" (Liesel Nygard, "Pope Leo fires back after Trump insults him: 'It’s ironic,'" MassLive, April 13 of this year). Fowler likely would classify all this differently, however; he would, I think, have Leo's remark as either satire or invective, what Leo thinks is irony as not a form of humor at all (since Fowler doesn't seem to account for the unintentionally humorous, or for that matter for self-deprecation), and what Morissette thinks is irony as "the sardonic." The motive or aim of the sardonic is self-relief, its province is adversity, its method or means is pessimism, and its audience is oneself (op. cit. Fowler, p. 253).
What I think makes this an interesting edge case in terms of pragmatics and Econian semiotics more generally is the possibility that Morissette's song produced more general acceptance of broader senses of this term. It seems likely, at least for some speakers. When she asks us if we think the situations in the lyrics are ironic or not, the malapropism queen might actually change our understanding of the word by clearly signaling that she expects us to answer a certain way. She made "fetch" happen on a grand scale. As Eco might put it, there is a difference between knowing what irony is and knowing whether and how one's aesthetic experience might benefit from considering something ironic or not (op. cit. Eco, pp. 203-4; admittedly this is my own gloss on an analogy that Eco does not seem directly to extend this far. A little too ironic. And yeah, I really do think).

Just an observation.