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not cool man 

when someone does something that is not acceptable, "Not cool man!" is usually an appropriate phrase to inform them that what they did was not nice, cool, funny, or tolerated by society, or just you.
Uncool guy: My butt is so awesome....
Cool guy: Not cool man!

Not cool 

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.
_ _ _ _

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"
Not cool by Psych! December 28, 2005

Not cool 

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!

Not Cool Bro!! 

The phrase of choice of a very loud Armenian male population, especially from Glendale, CA when they disapprove of anything not to thier satisfaction. Normally said in a very loud, booming voice with a rolling 'rrr'. This phrase is used mostly in driving situations where the all too perfect Armenian driving style has been disrupted in some way.
Shouting from his driver' side window - "Hey BRO! Not Cool Bro! Why you make lane change my lane when you KNOW I coming BRO!?? NOT COOL BRO!!".

you're not cool 

a useful phrase that comes in handy when some dumbass does something 'cool'.
but really. it's stupid.

you're not cool.
actually. you're about as cool as this definition.
that makes sense.
you're not cool by sammy____ September 13, 2006

Not cool 

That shit just is not cool, man. Why'd you desert your homies at a time of need?
Not cool by Anon255 February 13, 2013