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It seems like it should mean "if they were any better of a person, this wouldn't have happened to them" (which is quite negative), but it's always used in a way that implies a meaning of "no person is better than them" (which is obviously positive). How does the common usage make sense?

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    I most often hear "couldn't happen to a nicer person", and, when not being said ironically, it means that fortune has smiled on a person who well deserves it.
    – Hot Licks
    Commented Apr 14, 2016 at 19:49
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    It happened to the best person it could have happened to.
    – Drew
    Commented Apr 15, 2016 at 0:37
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    The implication is that it couldn't happen to a better person because there is no better person (for it to happen to). So it means "It happened to the best person for it to happen to."
    – herisson
    Commented Apr 15, 2016 at 1:02

4 Answers 4

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It typically means that the person to whom it happened (whatever it is) was best suited for it. The thing happening is typically positive, so it might be rephrased as

No person could be more deserving (of it).

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I do not believe it even means or implies that it couldn't have happened to someone better (than you).

Despite this there is often a dichotomous sense. If the thing that happened is pleasant - then the remark is a compliment.

However if it was unpleasant, saying it (usually about a third party, who is not present) provides an ironic twist - but essentially meaning they got their comeuppance.

E.g. A known pilferer has his wallet stolen. So someone says It couldn't have happened to a better person.

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  • +1 I'm familiar with: "It couldn't have happened to a nicer guy", and it's never meant as a compliment.
    – ab2
    Commented Apr 14, 2016 at 19:51
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    I don't think I have ever come across this expression used ironically: only in a complimentary way about a 'good' person.
    – TrevorD
    Commented Apr 15, 2016 at 23:25
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    @TrevorD Really? My understanding is exactly per Wiktionary.
    – WS2
    Commented Apr 16, 2016 at 8:15
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    @WS2 Yes really! My understanding is as in the accepted answer by phoog.
    – TrevorD
    Commented Apr 16, 2016 at 16:33
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First one must interpret the idiom in it's non-ironic, non-hyperbolic sense. It means that "it" happened to person who is absolutely the best/nicest guy that "it" could possibly happen to -- for once fate has appropriately rewarded goodness.

However, the idiom is never used without hyperbole, so (in it's non-ironic sense) it really means that the person to whom this happened was "pretty good" and/or "pretty nice" (though probably not the absolutely best/nicest guy in the Universe) and, as a result, deserved the (presumably beneficial) "it", whatever "it" is.

However to the second power, the idiom is probably more often used in an ironic sense than not (though either is possible), and when used ironically, it generally means that the "guy" mentioned "got what he deserved" -- the punishment suits the crime, as it were.

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  • Ok. I've re-read it and I see what you mean. However, you must agree that your wording could have been more explicit, and has contributed to the confusion. I do not want to get into a protracted discussion about this, so on that basis I will delete my comment.
    – WS2
    Commented Apr 16, 2016 at 19:11
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I know people sometimes, maybe even usually, mean this as a compliment, but to me, this reads as an insult, and the use of it as a compliment makes no sense.

I hear this mostly when something bad happens to somebody, for example, a losing streak for the Yankees, and someone says, "Ha! Couldn't happen to a nicer team." I interpret that as meaning, I'm glad the Yankees are losing, because I wouldn't wish this on a nicer team.

It makes no sense to me when someone gets a promotion and someone else says, "couldn't happen to a nicer guy". What, really? This most definitely could, and should, happen to a nicer guy. In fact, wouldn't you rather want this to happen to a nicer guy? Of course you would. So would I. So what is it you're really trying to say here? That the newly-promoted person is the nicest guy you know? OK, then maybe say, "There's no nicer guy I can think of to receive this honor." That's very clear, direct and unambiguous in its praise. Otherwise, implying that a nicer guy couldn't have been promoted, when that's not at all what someone meant, seems intellectually lazy, as in, he's not really sure what it is he's trying to put across, or else he doesn't know how to effectively put across what he is thinking.

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