What is You Know You're Cool When?
1.
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:
1.
when u get a girl drunk/high/or slip a pill in her drink then when u fuck her, you fuck her doggystyle but with her head close to a hard..