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)"

by the coolest guy November 8, 2006
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You're just too cool to bother with any details of anything.
And surpass the level of 'Epic coolness'

This line CANNOT be said. Unless you strike a cool pose right after.
Mother: Sweetie, you have weird rocker friends.
Daughter: I'm not a rocker!
Mother: ...Sorry. You have weird goth friends.
Daughter: I'm not goth!
Mother: Then what are you?!
Daughter: Mom! When you're this cool, You don't bother with the details. ;D
by Ashley ;D June 18, 2008
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