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Awkward Squad 

Awkward Squad is the name given to that group of people in any organisation who cause problems and difficulties. They are apparently normal, everyday human beings, but when they get together, things just go wrong. They are not necessarily troublemakers, although in some instances they can be, but some strange synergy causes things to go wrong in their collective presence.

The origin of the word dates back to just after the Second World War when National Service was compulsory in Britain for males over the age of eighteen. This meant that all sorts of people, some of whom were totally unsuited to military service, were inducted into the armed forces. That they were unsuitable quickly became apparent, and they tended to be grouped together to keep the clumsy, the unwilling, the careless and troublesome in one unit which became known as the awkward squad
"Get ready for problems, the awkward squad is doing a computer presentation."
Awkward Squad by AKACroatalin April 11, 2015

Brown Star Award 

The brown star award is earned after successfully having anal sex for the first time.
Joe Smo - Dude I just screwed Nikki in the ass..it was awesome. Joe Smo's Buddy- Dude you got the brown star award..thats Epic.
Brown Star Award by 1 with Nature February 12, 2015

awkwardist 

An awkwardist: someone who makes every situation awkward.
He just stood there in the middle of the whole group and started saying weird things about all sorts of people, including some of the people that were actually there. He's such an awkwardist - he does it all the time.
awkwardist by Danlod2 May 5, 2023

Granny Awards 

An annual celebration of Archaicisms, primarily serving as an ego defense mechanism for Boomers (and other old people.)
Nominated for 2014 Granny Awards Rock Album of the Year:

Zeppelin, Sabbath, Bowie and Neil Young

-- Four acts that were "too hip to be square"* around 1970.

Kings of Leon and Queens of the Stone Age

-- Named after a passe form of government and a truly ancient Age of Tech.

How desperately we cling to illusions of youth and relevancy. -- Citizen of the Galaxy

* Once upon a time, even Before the Flood, contemporaneous fans of "Old Blue Eyes" and the "Candy Man" embarrassed themselves with such phrases, in a vain attempt to sustain their own relevance. Please, STOP THE MADNESS!
Another term for "award" that originated from a typo the Monke brained Connor of Trash Taste while typing the Reddit post for their podcast's anniversary.
Guy1: Hey have you watched the Trash Taste Awardw?
Guy2: you mean awards?
Guy1: no, it's awardw
awardw by Rain-nin May 28, 2021

Socially Awkward Butterfly 

Someone who can be easygoing and talkative when in situations that comfort them, still jumping between different friend groups as long as they are comfortable. However, this person may also show awkwardness in uncomfortable situations, like talking to someone new or giving a presentation.
Rod: "Did you know that Terry is a socially awkward butterfly?"

Mark: "Really? What does that mean?"

Rod: "It means he's confused."