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on the square 

A member of the free mason's. The free masons have a number of rituals one of which involves a novice showing there development by moving around a square that it on the floor of a Masonic Hall
I didn't know "He " was on the square .
on the square by Barry Otter August 22, 2023

On the Square 

A Freemasonic term based on the square level used by ancient & modern stone masons. According to "Encyclopedia of Freemasonry, Vol II, Albert Mackey" the meaning of the square is:

"... In Freemasonry, it is a symbol of morality. This is its general signification, and is applied in various ways: 1. It presents itself to the neophyte as one of the three great lights; 2. To the Fellow-Craft as one of his working tools; 3. To the Master Mason as the official emblem of the Master of the Lodge" (Enc. of Freemasonry Vol II, Albert Mackey pp. 708)

Thus, the term "on the square" is much the same as "squared away," or "fair and square." To talk to a person "on the square" means to talk in a blunt and straightforward manner, as not to beat around the bush.
Let's talk 'on the square' (to speak candidly, bluntly, and in a straightforward manner)
On the Square by SerenityJosh February 27, 2025

kidding on the square 

joking, but also meaning it
kidding on the square by Anonymous November 9, 2003

lying on the square

A term created by Al Franken, used to reference when someone is saying something as a joke, but they know that its the truth.
"Sure, I'm the bad guy" joked Tom, but Jack knew he was Lying on the square.

winning on the square 

To win, or achieve success without any foul play, cheating, or manipulation.. By completely fair & ethical & honorable means.
Congrats on coming in 1st place John. You were awesome! I know you worked hard, & all that practice paid off. Thats straight winning on the square!

Joking on the Square 

A diplomatic way of telling a friend their outfit sucks, their boyfriend is ugly, they need to use more conditioner, etc. by making a joke about it like you’re kidding.
Usually they will get the hint without getting mad.
Hey Megan, (laughing) man I love those jeans, I haven’t been able to find those lately, did you get them at a garage sale?
Megan: Are you joking on the square dude??
Joking on the Square by Richfolk September 23, 2021
More from Urban Dictionary
A girl who does ballet and only talks about ballet. Her schedule is filled with dance classes which does not allow her to do any other activity.
"Hey, do you know that girl Sally?"

"Yeah, she's kind of annoying. All she ever talks about it ballet."

"Wow, what a Bunhead."

"Hey Sally, you want to hang out this weekend?"
"I can't, I have dance."
"You're such a Bunhead."

"Yeah... I know."
Bunhead by Jen00 October 24, 2014
Word of the Day on October 6, 2026

trucker's tan 

A sunburn or suntan focused on the left arm. It is caused by the left side of the body being the only half that gets exposed to sunlight while driving. Presumably, it would be located on the right side of the body in countries where they drive on the left side of the road.
I had a trucker's tan after driving for 10 straight hours on a sunny day.
Word of the Day on October 5, 2026
The phenomenon where adults salivate at children's toys
Every time I walk into the toy aisle, I catch myself kidulting over the latest action figures and LEGO sets!
kidulting by Emotional Cruiser October 12, 2025
Word of the Day on October 4, 2026
British slang for a scientist or technical expert, esp . when the speaker is not certain of the expert’s specific field of study. Not necessarily derogatory, but typically used by persons without a technical background. In the US, the equivalent would be “egghead”, “squint”, or “geek.”

Origin of the word is unknown. Started sometime in World War 2. Given the typical evolution of British slang, could easily have started because what these experts did was confusing or “baffling” to the common person.
According to the boffins downstairs, the murderer used a serrated blade.
Boffin by Agnon February 11, 2023
Word of the Day on October 3, 2026
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