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I stumbled upon this strange problem. The following sentence is grammatically correct:

It's better to be miserable and rich than it is to be miserable and poor.

Let's replace the second "it is" with its contraction:

It's better to be miserable and rich than it's to be miserable and poor.

Why does the sentence seem grammatically wrong, or at the very least, awkward? It could be explained as merely bad style, however, stylistic issues are not grammatical issues and are often not awkward either. Moreover, substituting noun-verb pairs for their contracted form technically shouldn't change the semantics of the sentence.

user148298
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    Have you thought about the possible ambiguity between its and it’s as a source of the disconnect? – George White Mar 02 '23 at 20:52
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    Your comments gave me something to think about and now I am getting scared! Are we humans doing exactly what ChatGPT is doing with language, predicting the next likely word? It's way more common for "its" to follow "than" than it's for "it's" to follow "than." So we're not all that special and now we must face AI bots who will outsmart and enslave us all...God help us.... – user148298 Mar 02 '23 at 21:39
  • @Barmar "Can't be used" means it's grammatically incorrect? Right? If use of contractions do change meaning perhaps they should be illegal. Boy, English is a real mess! – user148298 Mar 02 '23 at 21:44
  • Contractions aren't really a grammatical matter, it's more about whether it's idiomatic. – Barmar Mar 02 '23 at 21:46
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    I'd guess you want to emphasise the later "is" due to the shape of the sentence, but you can't emphasise "it's" (or at least it's very unnatural to do so). Unless someone has written a paper on this, I'm not sure there will be a definite answer. – Stuart F Mar 02 '23 at 22:50
  • *...Strong verb forms, of course, can't be contracted.* And in the cited example ...than it is* to be...* is a "strong" form used for *contrast. Compare It sounds worse than it is, which can't* be contracted to It sounds worse than it's** – FumbleFingers Mar 02 '23 at 22:53
  • Well at least I learned that English has a very bad UX. It's the Microsoft Windows of languages, full of bugs and inconsistencies we spend a majority of our formal education learning but never mastering. I just wish Anglophones would acknowledge it. – user148298 Mar 03 '23 at 04:57
  • Let's separate the comparative adjective into "more" and a base-form adjective:

    It is more good to be miserable and rich than it is to be miserable and poor.

    This is elliptical for:

    It is more good to be miserable and rich than it is good to be miserable and poor.

    We elide the second occurrence of "good", but removing it leaves a grammatical trace. It's not grammatical to contract a verb that comes just before a trace. Adapting FumbleFingers's example:

    It sounds more bad than it is.

    This is elliptical for:

    It sounds more bad than it is bad.

     – Rosie F Mar 03 '23 at 06:13

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