What is You Know You're Cool When?
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Used as an expression when someone does something so randomly stupid its funny. its sort of like, the action is the word after the "u know ur cool when" so "u know when ur cool when (you've peed in a can)"
guy:i just peed in a can
girl:You know you're cool when
Random Words:
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A crap character from Star Trek: Deep Space Nine who's just like Captain Kirk only even more crap and he's Black
Captain Sisk..
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when something that is humorous or witty someone may say "i split my sides" refering to them laughing very hard
tim: whats 30..