I’ve been struggling with this one for a while, and it’s something I’ve tried typing/ writing on numerous occasions but it never looks correct in my mind. When speaking, I tend to say “should not have” as if it was one word (I.e I should not have had that donair last night) and when I picture the contraction for this word it looks like it would be “shouldn’t’ve“. Is this proper English in the first place?

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    The second apostrophe is generally left out for aesthetic reasons, but yes, that’s it. Or shouldna If you prefer. Whether it’s ‘proper English’ depends entirely on whose definition of what’s ‘proper’ you choose to adhere to. It’s perfectly proper if you go by my definition. – Janus Bahs Jacquet May 4 '19 at 12:06
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    What @Janus said. Google Books seems to have less than a dozen written instances of the "awkward-looking" she shouldn't've, but there are probably thousands of instances of she shouldn't have. – FumbleFingers May 4 '19 at 12:33
  • It's commonly written "shouldn't of", which is a homophone. But you probably don't want to do that, as people might think you don't understand grammar. – Peter Shor May 4 '19 at 12:48
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    @mahmud koya ... that's only good advice if you're writing formal English (as google developers are supposed to be; hence this advice in their style guide). Shouldn't've would be fine in dialog in a novel, or email to a friend. – Peter Shor May 4 '19 at 14:36
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    ’Tisn’t too much to wonder where you’ll’ve gotten the idea that contractions are ever “proper”, nor to wonder what “proper” even means. – tchrist May 4 '19 at 17:51