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perceived coolness whore 

The annoying individual who claims to be interested or expert in almost any topic that anybody else in a group refers to as cool, often to the extent that their involvement in so many activities and interests, or in a more oscure pursuit or fetish, may seem dubious.
"Hangliding looks cool" eliciting the response "Oh, I LOVE to hanglide, I'm an experienced hangliderist!"

or

"I have a friend who is into CBT" followed by "Ooo, CBT is the coolest - I do it all the time!" leading the original speaker to ask the perceived coolness whore to define CBT in semi-polite company.

At their worst, a perceived coolness whore might stumble, late, into a conversation about female contraceptives or male pattern baldness and, upon hearing a prescription drug name, will claim to have once done lines of the afore-mentioned drug off the back of a hooker at a Hollywood party.

Coolest kid

Coolest kid could be anyone.
You wouldn’t know who.
LAME Kid1: Hey, who’s the coolest kid around here?
LAME Kid2: Only the one and only Coolkid89!
LAME Kid3: WOW! Their name even sounds cool!
Coolest kid by Not Niki December 8, 2021
the most "cool" or the "best"
"man, that car is like the coolest thing I've ever seen!"
coolest by Will L June 22, 2005

Coolest cat in the Barn

The act of being extremly cool and amazing, yet resembling the awsomeness of cool barn cats.
Amanda: WOW, My pet fish is SO cool!

Hayley: You bet, it is the coolest cat in the barn!

Maintain Coolness 

(main~tane kewl-ness)
adj. Keep it real, Be Cool, Shit wired tight, Maintaining, Maintained Coolness
1. An extreme state of Maintaining
2. When one is in a troublesome situation and does not give in to the pressure, temptations, or does not let negitive chance effect them.
3. To keep a high level of bad assery at a club/bar/party/home alone.
Eventhough that lying bitch cheated on Boxhead, he maintained coolness and obtained his first booty call one week after he shunned that slut. He later obtained his Grey belt at a second-degree level two weeks following. He definitely can Maintain Coolness.
Maintain Coolness by Boxhead January 19, 2006