What is Square Peg Syndrome?
1.
A case of extreme persistance and/or stubbornness in trying to force something that just won't fit, esp. physically but also metaphorically. Often caused by a desire for efficiancy that ends up counterproductively wasting time and ending with a precarious outcome or damage if left unchecked.
There was simply no room left in the cabinet, but Joel and his Square Peg Syndrome kept trying to stuff that Pop-Tarts box in there.
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(V.)You fool around with a girl. She fools around with a different guy. You fool around with her again. This all takes place within a sh..