Double Conjectures - Grammatically Correct or Not - You Decide?

I think "wouldn't've" is perfectly correct. It's just that it's very casual; you hear it much more in speech than writing. The only time you'd really need to use it is for a piece of literature or poetry with character dialogue in the "local color." Contractions of all kinds are too casual for academic and business writing, and a double contraction like "wouldn't've" would be just too weird for journalistic writing.

Now that I think about it, I think I say "wouldn't've" all the time.

The usual usage when giving a character dialog is to use a phonetic spelling rather than a double contraction. It's usual even when it's not a contraction. I'm accustomed to seeing "would of" and "could of" and "might of" when there'd be sense in "would've" and "could've" and "might've".

The spell checker here won't accept "there'd", "could've" and "might've" in the previous sentence. I've been irritated by this.

The "could na", etc. is only natural in areas where Scottish is in the heritage. I could nay understand him. It's not a sloppy dropping of the t in not. There was ne'er a t in nay.

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Conjectures and contractions are two wholly different things. But in your example, "wouldn't've" makes sense, but it's gramatically incorrect -- because that's the rule.

No one actually says "wouldn't've", "shouldn't've", "couldn't've", or even "hadn't've". They are actually attempting to say "wouldn't have", "couldn't have", "shouldn't have" and yes, "hadn't have". It's just lazy speech, tacking the "na" at the end of the contraction, in place of the word 'have.' Our ears hear the 'na' replacement of 'have' sounding like the word 'of.'

Rather than double contractions, look at them as two contractions: couldn't 've, shouldn't 've, can't 've.

If you are writing something and want to show what someone's speech is like, you could do this. It would show their dialect or lack of education. Don't use it in your prose or you will show your own.

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We pronounce it like "couldn't've, but it's not correct - couldn't have is correct. BTW, it's "contractions."