Many people mess this phrasing up. In fact, most people haven’t even noticed when someone says he “should of” or “should not of” done something. The phrasing generally points to a regret, but the improper word usage is also regrettable.
The same issue crops up with “could” and “would.”
When we say a person “could have,” “should have,” or “would have” done something, we are using a conditional verb tense that includes a form of the verb “to have.” The word “of” has nothing to do with it. It simply doesn’t fit.
Even if you think you “shoulda coulda woulda,” it wouldn’t be right.
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