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1.
A stupid way of saying "should have".
Person: I totally should of bought the bike, duuuuude.
Me: DIEEEEEEEEEEEEEEEEEEEEE! *stabs to death*
von Blizzleair 21. September 2003
 
2.
What idiots say instead of should have. It makes most people want to stab the offender to death.
"I should have not said "should of", becuase after I did I got a screwdriver to the face."
von Uller 22. Juni 2005
 
3.
Ignorant way of saying, texting, or posting on facebook the contraction of should have (should've). Especially pathetic when supposedly educated people use the phrase.
I should of paid attention in high school English class so my participles wouldn't be dangling.
von dookeyboy 21. November 2010
 
4.
Misspelling of should've (should have)
He should of gotten a Dreamcast
von Darxide 18. August 2003
 
5.
Wrong writing and saying of 'should have'
Many people mishear 'should've' and hear 'should of' instead. Same procedure with 'must've' and 'could've'
I should of learnt some better English.
von satrox 17. Oktober 2012