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The first person who typed “should of” probably heard of it in real life that was meant to be “should’ve”, they typed “should of” online and readers thought that it’s grammatically correct to say “should of” which is in fact wrong and it became widespread throughout the years on Reddit.

I hope something could start to change.

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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).

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“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.

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Just read the second (or the first, but that is more technical) link I shared. Some native speakers do in fact seem to say “should of” even when the “of” is stressed, so in their dialect it would be grammatical.

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Isn’t “have” either an auxiliary verb or verb and “of” a preposition?

Are these acceptable? If yes, why? If not, why not?

  • I of heard that story before.

  • Diane of already gone.

  • John ofn’t phoned, of he?

  • I ofn’t visited London before.

  • Of you seen Roz?

  • Of she been invited?

  • 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.

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Isn’t “have” either an auxiliary verb or verb and “of” a preposition?

Yes.

Are these acceptable? If yes, why? If not, why not?

No, because you constructed them by merely replacing the verb “have” by the preposition “of” in situations which have nothing to do with “of” after “should”/“would”/“could”. I’m not sure what point you’re trying to make, since neither I nor the people I cited ever claimed that this should work in the first place. The claim of in particular the author of the first paper I cited is that for some speakers there seems to be a novel construction modal verb + “of” + past participle, not that the preposition “of” has the same function as “have” in this case or in any other (in this case, the novel construction as a whole would have more or less, but not entirely the same function as modal verb + “have” + past participle, but “of” would still be just a preposition).

I don’t know man, Oxford Dictionary (click Grammar Point to expand) says that […] it is definitely considered wrong in standard English.

Yes, it certainly is considered wrong in standard English, but the interesting thing is that in some non-standard dialects there might be genuinely a novel grammatical construction which actually uses the preposition “of”. I mean, you don’t need to find that interesting, but I do. And if that is indeed the case, it would mean that the speakers of those dialects are not making a purely orthographic mistake like when people confuse “they’re” and “their”, for example, but are rather speaking or typing in their dialect.

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…the reason “in some dialects of English native speakers really do say ‘should of’ etc” is phonetics. Kids hear “should’ve” and repeat it phonetically, before learning the actual words or their meaning. Combine that with the awful state of education and literacy in the USA (and other countries etc) and voila, you’ve got some armchair internet expert justifying it with some big words trying a weeeee bit too hard to make it work.

Then you’ve got teachers who still gaf and know their shit who will correct this before middle/high school, and no, last I checked it was never added to the dictionary or considered correct. Language of course is living and ever changing, but the line must be drawn somewhere lest we devolve into shouting and grunts like neanderthals

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the reason “in some dialects of English native speakers really do say ‘should of’ etc” is phonetics.

What the author of the first link claims (and the second link explains in a more accessible way), is that it’s not just that for everyone. Like some native speakers really do say “of” sometimes, even when it’s stressed and doesn’t sound like “'ve” at all. So for them it wouldn’t just be a spelling mistake, but a different grammatical construction.

last I checked it was never added to the dictionary

Some dictionaries (e.g. Merriam-Webster) actually do list “of” as an alternate spelling of “have” (not in the sense of a genuinely different grammatical construction though).
Obviously it’s not considered standard by anyone, which is also why teachers call it incorrect, who (should) teach the standard dialects.

Language of course is living and ever changing, but the line must be drawn somewhere lest we devolve into shouting and grunts like neanderthals

Language changes whether you and I like it or not, and efforts to stop that from happening are generally unsuccessful. You can also rest assured that a simple change in what is considered correct grammar or spelling (which, as far as I know, nobody has been suggesting in this case so far, but it seems like that would be the “worst-case” scenario from your perspective) would not lead to us or language “devolving”. Also, while we don’t know anything precise about how Neanderthals spoke, most likely they sounded more or less like us and did not communicate by “shouting and grunts”.

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