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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"
by Psych! November 27, 2005
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2
Failing to be cool. Trying to be cool and being just pathetic.
-John: Hey, girls! Look at my new trainers! I think they're great!
-Kate (to her friends): This guy is just not cool.
by sicko2 March 02, 2008
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3
When someone has done something which causes you anger and displeasure. You respond by throwing down any item which you are currently holding and yell: "NOT COOL!". Of great importance: the item which has been throw down is now considered community property and may be taken by anyone witnessing said event.
Cool Guy: (walking into a room of friends/coworkers eating burritos) Dude, where's my burrito?
Not Cool Guy: I think they forgot to make it. Or maybe I forgot to order it. (smirks)
Cool Guy: (throwing down container of guacamole -- which he intends those in the room to now eat) NOT COOL!
by not cool guy eating a burrito January 14, 2014
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4
The ultimate phrase to describe those who are at times 'lame' as the terminology an American would maybe use.
by DarkestMaiden March 09, 2007
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5
That shit just is not cool, man. Why'd you desert your homies at a time of need?
by Anon255 February 13, 2013
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