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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Its when your having sex with a chick doggie style over a toilet while she's throwing up from drinking to much.
I gave that chick ..
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The over-saturation of African American opinions and views about Obama's Inauguration.
Jeff: Why is everyone on television suddenl..