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pwn-square 

In a cyber debate, it is common to see people say PWNED! when they are right. When a debate gets very heated, it is possible to pwn-square a person, or just completely own them in an intense and utterly baffeling fasion. This is known to have occurred one time in history, between the legendary UROW and the mini cup-cake D-Mac. A Pwn-cubed is unheard of, so don't even try.
It's proof read not proofread you mother fucker!

No, see, on dictionary.com it says proofread! AHAH! I pwn-squared you!
pwn-square by UROW May 22, 2007
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skip square 

Someone who is missing out on an activity everyone else is enjoying and/or being a debbie downer.

-Derived from drug culture, someone who would buy a tab/square of LSD that was skipped over by the dropper used to apply the drug onto it. Therefore that person is missing out while their friends are tripping.
"Last week John acted like a total skip square at the party, standing by himself while everyone else was chillin'"
"You hear about Brandon buying a sheet of blank paper thinking it was acid? lmao what a skip square"
skip square by TophatDemon June 13, 2018

4-Square 

A recces favorite. Consist mostly of arguing about silly things and who is out (most of the time it is pretty obvious. You waste more than half of your recces yelling with everyone. People just do NOT go out when they are supposed to. It is a waste of your recces with all the arguing and disagreements. On the other hand a pretty fun game. :)
Hey do you want to play 4-square with me at recces?
Not really
Why not
I dont know, everyone just argues the whole time and it is a waste of recess
4-Square by Artic Fox 5227 May 30, 2019

Triangular square

A square that is triangular
Oh shit, daddy the triangular square is big

love square 

when 4 people (or 2 if there’s superheroes) are involved in some ridiculous love mess
this is an example of a love square: marinette likes adrien but adrien is also chat noir who likes ladybug and ladybug is marinette but ladybug does not like chat noir and adrien calls marinette “just a friend”
love square by taylorswiftrailme November 29, 2020

Washington Square Syndicate

This Syndicate founded in October 2022 in Savannah, GA in the unanimously voted best Square in the city, Washington Square. The first of its kind, a socially democratic syndicate that is not to be challenged or messed with. The Syndicate initially formed as an unorganized gang, and as their numbers and muscle grew, they’ve become an elite group of organized rabble rousers that seem to grow stronger by the day. Rumors have flew around Savannah since establishment, every one worse than the one before. Although one thing seems to be known, your pets are safe with the Washington Square Syndicate, you on the other hand… (dun dun dun)

While in its early days, the Syndicate is something this country has never seen before; potentially starting a movement of organized mobsters we haven’t seen since the early days of the Italian Mob.

If you are in Savannah, watch your back. If you end up near Washington Square: pray.
The Washington Square Syndicate is not to be messed with.

square one 

When you try to make a bad situation better, and end up with the original problem.
(The term comes from a board game, where you progress until something sends you back to square one.)
I wanted to make a lot of money, so I saved up a lot, bought a business, and gambled all my money away. Now I'm back to square one.
square one by Thadanator July 23, 2008