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The other day I struck up a conversation, about economics of all thing, with a stranger whose political beliefs were quite different from my own. It was a little bit of a teaching opportunity as I introduced him to some new concepts. And while the conversation was respectful and engaging, I kept going over it in my head afterwards, wishing I had phrased certain things in a different way, wishing I had mentioned certain ideas and excluded others, and generally feeling like I did a really poor job of presenting my arguments. Now, I certainly feel better prepared if a similar situation were to arise again. But I had trouble shaking the feelings of "I wish I would have said that..."

Certainly I can refer to these feelings as regret. But I'm wondering if there's a word or idiom in usage that's more specific to this type of scenario?

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There's l'esprit de l'escalier ("staircase wit"), which Wikipedia describes as "the predicament of thinking of the perfect reply too late".

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    My thoughts exactly! I was just scrolling down to the "Your Answer" section to post this myself, and here it is! I can't help feeling it's a bit ironic that non-native Anglophones come to English Language & Usage looking for a word or expression with this meaning, but the best we can offer is a French expression. To my mind, "staircase wit" is a sad reflection of the fact that we couldn't think of any better way of expressing it, so a crap literal translation is all we have by way of comparison / competition! :) Oct 11 at 15:03
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    @FumbleFingers: I was thinking the same. Departee maybe: repartee+departure? Oct 11 at 15:17
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    @OldBrixtonian: Haha! I tend to be a bit dismissive of puns ("the lowest form of wit"?), but that one tickled my fancy! Now all I need to know is that French term for "witty r/departee that I must write down and remember while I look out for an opportunity to dazzle everyone with my wit" :) Oct 11 at 16:41
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    Treppenwitz is another term with the same meaning.
    – Casey
    Oct 12 at 0:17
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    Related: Fridge Logic Warning: TVTropes link. ;)
    – PM 2Ring
    Oct 12 at 3:41
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After the fact

As an example

I only though of a good explanation after the fact.

After the fact generally means the information is too late to be of use. It's generally used to express a wish you did or said something differently, but it's too late now.

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Possibly Afterwit:

  1. Wisdom which comes after the event.

  2. A good comeback, retort one thinks of only after the end of discussion or after leaving a social gathering. Synonyms: l'esprit de l'escalier, staircase wit, (neologism) retrotort

https://en.wiktionary.org/wiki/afterwit

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The word you may be looking for is hindsight, which refers to thinking more about a situation you were in previously. You may in particular be looking for the idiom "hindsight is 20/20", which refers to the feeling that you now better understand a prior situation and know what you should have done differently.

The idiom is derived from the facetious idea of hindsight as a kind of vision, which it isn't really, and the fact that 20/20 vision is considered to be perfect--hindsight is perfect vision, and you always know what you should have done after it's too late.

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perseverate - Repeat or prolong an action, thought, or utterance after the stimulus that prompted it has ceased.

Nice, because you can call your condition perserveration.

That said, perseveration is often more pathological. But I've heard it as a synonym of sorts for stew over, or

dwell on/upon - to think, speak, or write about at length or with persistence; linger over.

... those just don't turn into nouns quite as well.

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