should of is probably a product of phonetic typing (those who just type the letters that match the internal audio) or when siri first launched voice typing and no one bothered to check it. Edit: Should of should've died a long time ago tbh. could do with a mini-crusade.
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People writing of instead of 've is pretty well attested before Siri even existed so I doubt that has much to do with it
Shoulda coulda & woulda are all intentional uses of slang, IMO and also exceptable online discourse.
Anyone else also say "shouldn't've" instead of "shouldn't have"? No? Just me?
“shouldn’t’ve”
In Canada - we will've stolen it from Ireland or Scotland - we'll jam three contractions onto the end of a word. I forget which case it is, but I run across or write it almost weekly. It's like a "will have been" kind of super compound phrase.
English contractions are very hard and I have been trying to be better at them. For other users like me who struggle with English, text generators like the ChatGPT can help a lot if you ask them to correct for you and they will give you tips. Be careful if it is online one like ChatGPT though, it isn't private!
While it is true that "should of" etc. can easily originate from a confusion between "'ve'" and unstressed "of", which sound identical, the statement
"Should of" is incorrect
itself is at least a bit misleading and prescriptivist in its generality.
Interestingly, there seem to be at least some native English speakers who genuinely do say "should of" (with a stressed "of") sometimes. This paper for example argues that people who say "should of" really do use a grammatical construction of the form modal verb + of + past participle. One argument the author mentions is that this would also explain the words "woulda", "coulda" and "shoulda", since "of"->"a" is quite common in general (e.g. "kind of" -> "kinda"), but "'ve"->"a" basically doesn't occur elsewhere (e.g. no one says "I'a" or "you'a" instead of "I've" or "you've"). Another is that the reverse mistake, i.e. using "'ve'" in place of "of" (e.g. "kind've"), is much rarer, which is a clear difference to e.g. the situation with "they're"/"their"/"there", where people use these words in place of the others in all combinations frequently. I recommend this blog article for a much longer discussion.
Also, whether genuine mistake (which it almost certainly is in many cases, although probably not all) or different grammatical construction, YSK that "should of" etc. didn't just become popular recently, but have been used for centuries. E.g. John Keats wrote in a letter in 1814: "Had I known of your illness I should not of written in such fiery phrase in my first Letter.". Many more examples (some older as well) can be found e.g. here or here.
TL;DR: While in many cases "should of" etc. can well be a mistake, originating from the fact that it sounds identical to "should've" when unstressed, there is some interesting linguistic evidence that at least in some dialects of English native speakers really do say "should of" etc. (i.e. in those cases it is not a mistake, merely non-standard/dialectal).
"Should of" is grammatically incorrect, regardless of whether the user/speaker is aware of its incorrectness. It's a fact, and a fact per se cannot be misleading. It's as simple as that. Linguistic conventions, as you've illustrated, can be formed over time, but that again doesn't take away from the fact that such usage is grammatically incorrect to begin with.
Isn't "have" either an auxiliary verb or verb and "of" a preposition?
Are these acceptable? If yes, why? If not, why not?
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I of heard that story before.
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Diane of already gone.
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John ofn't phoned, of he?
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I ofn't visited London before.
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Of you seen Roz?
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Of she been invited?
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They still ofn't of any news when I spoke to them yesterday.
I don't know man, Oxford Dictionary (click Grammar Point to expand) says that https://www.oxfordlearnersdictionaries.com/definition/english/have_2
A common mistake is to write ‘could of’ instead of could have or could've
~~I could of told you that.~~
I could've told you that.
The reason for the mistake is that the pronunciation of ’ve is the same as that of of when it is not stressed. This is a common error but it is definitely considered wrong in standard English.