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Why should I? 

If you want to know a word Search it in the search box.It Legitimately Says “Type Any Word”.
So type your word. Don’t ask why.
Kevin: “Why should I?”

Helen: “Did they really just ask the search box why they they should search any word?”

Johnathan: “I think they did. Why the hell would you ask that to a search box?”
Why should I? by Jobn126 July 8, 2020
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Why should I care 

When you totally don’t care
Why should I care by Elagss May 6, 2020

Why should I tell you? 

It means they don't know, or are a stupid troll.
"Ok, if you're a genius, then what's the square root of 6456?"
"Why should I tell you?"

Why Should I Wear a Mask? 

The question anti-maskers worldwide have been asking themselves, because in their minds, Covid or not, they won’t die, as their Creator is the One who determines their number of days on earth, although corporate prayers from righteous men and women could prolong their stay a little bit longer.
“Why should I wear a mask?” and “Why should I be jabbed?” might outwardly appear to be selfish questions, but spiritually or philosophically speaking, they are nontrivial questions that politicians and religious leaders often try to shun away from.

why should i live 

There is no point only pain
"why should i live"
why should i live by Kirashina November 13, 2022

Why should I give it to you? 

Because I want it more than anyone else even cares.
Bartholomew Bartholomewson "Why should I give it to you?"

Hym "That" ☝️

If I can make you do what I want and get away with it, why should I not? 

Empathy for one. In the absence of empathy, if the amount of energy takes for you to get me to do a thing supersedes the amount of energy required for the thing to be done then it wouldn't be practical for you to make me do the thing. Additionally, my awareness of my own mortality makes it impossible for me to be perpetually made to do thing because I can always just kill myself. It incentivizes harming you and the things you care about. It gives your enemies a de-facto ally. But it's intriguing that you think that there is only one reason...
JeerpJoop "If I can make you do what I want and get away with it, why should I not?"

Hym "Well, for starters, there's more than one reason. Secondly, you literally can't. You can only leverage (either) my desire to live against performing the act OR the hope that I may not have to continue doing it indefinitely. Which is how you get people to stay in your suffering cult. You leverage their desire to live and their hope that their suffering will end to get them to do what you want or behave how you want to behave. It's actually kind of illuminating to because if you're God rewards screwing people over then is it not evil? Sounds evil. It ties back into you not actually believing in God but rather believing that God is on your side and that it will forgive you if you do the opposite of what it said."
More from Urban Dictionary

square grouper

Nickname given to bales of marijuana thrown overboard or out of airplanes. Origin is reportedly from members of the US Coast Guard in the area of Southern Florida.
"Base we've got some square groupers floating outside of Miami harbor."
square grouper by slipsheet November 6, 2004
Word of the Day on October 7, 2026
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

Pee Calculus

When you have to pee in a movie but don’t want to miss anything, and must do the following mental equation: will the amount I have to pee cause enough discomfort to diminish my attention capacity for the remainder of the movie to an extent which is greater than the amount of the movie I would miss by making a mad dash to the restroom.
I saw Satantango last night, wonderful film but by the 5th hour I had to start doing pee calculus.
Pee Calculus by anorlondo October 1, 2026
Word of the Day on October 2, 2026
Literally "dirty" pronounced with a West Indian accent. Can also have a positive connotation, for example Sean Paul's album title "Dutty Rock".
"The girl is pretty but she corrupt and dutty!"

or, in a positive usage:

"Booya! That freestyle was dutty!"
Dutty by J Hall April 3, 2003
Word of the Day on October 1, 2026
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