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This describes someone who is constantly judging everyone and everything to be less cool than they are, because in their mind they're a true rebel in the know about everything. This kind of person mocks or rolls their eyes at anyone who they judge to be uncool, but only because they [imagine that] other "cool" people would hold such a view, and they feel they're in the know about how all the "cool" people think, and want to feel accepted by the cool crowd. They're [simultaneously] insecure and worried about maintaining their image at all times, and in case anyone might see them, they won't let themselves get really into or become [enthusiastic] about anything, lest that thing be thought of as uncool. Also applies to hipsters on the excessively surly and douchey end of the hipster spectrum.
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