An expression on how something is... well, not cool. Very similar to the following expression: gay, retarded, lame, etc.
"Dude, you got drunk and danced naked in the middle of the freeway while singing "Jingle Bells" in Spanish?!"
"Dude, I know. Totally not cool."
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Not cool situation: When you get an "F" on your math test because you studied the wrong chapter... three minutes prior to the test ^_^
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*Bitch slap* <---- Not cool.
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Boyfriend: "I have something to tell you..."
Girlfriend: "You love me? =)"
Boyfriend: "Uh, I'm gay."
Girlfriend: "What? NOT AGAIN! This is SO not cool"
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