Aweskward 

(1)When a situation is a combination of awesome and awkward, (2)especially when one deliberately goes out of their way to make a situation uncomfortable for others.

(1)"When i ran into my asshole ex-boyfriend with my newer, smarter, hotter boyfriend, it was totally aweskward."

OR

(2)"Let's show up at that party we deliberately weren't invited to. It'll be so aweskward."

Aweskward by LS Island October 18, 2008

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

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

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."

Socially Awkward Butterfly by PeterPieffer June 3, 2020

Awkward Crow 

The result of an awkward situation in which the topic is misunderstood or ignored by the other person. Signalled by the joining of thumbs, extension of fingers to create a bird like shape, raising them over one's head, making the sounds of a crow.

A Boy and Girl are sat together:

Boy: It wouldn't make any difference if I ate anything off your body, you're so flat chested it'd be like eating off of the table.

Girl looks vacant. Boy signals the Awkward Crow...

Awkward Crow by AggroBrantos January 14, 2011

That Awkward Magic 

One of that best bl you will ever read.

have you read the new chapter of That Awkward Magic

yes it made me cry

That Awkward Magic by thatmaxican4783 July 26, 2018