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guess what? 

bro do not fall for it. you think they are about get you with the most elaborate joke that you have never heard of but they are going to gut check you with the words"chicken butt" at this moment you must murder them because that joke is so unfunny that its funny.
(person 1 ) HEY GUESS WHAT BRO??
(person 2 aka the victim) what man?
(person 1) chicken butt.*starts laughing like the joker*

in all seriousness "guess what?" usually means that somebody is about to hit you with a joke or wants to tell you something
guess what? by yewy is innocent December 5, 2023
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Guess what? 

If the recipient asks, "What?", after receiving this question, there is a risk that the giver of the question will respond with, "Chicken butt". In the event that this occurs, the recipient will be shunned by their peers for being so careless.
Guess what?
what?
Chicken butt! hahahahaha
aw man...
Guess what? by GoofyGoober10 January 23, 2025

Guess you're taking the scenic route to the hole 

This phrase is said while golfing. to someone who isn't keeping their ball within the fairway. It usually means they're in the trees or hazard areas.
Your ball is about two inches off of the white house's fence. I guess you're taking the scenic route to the hole.

Guess the Price (Lankybox)

The videos targeted to teens that were made by Lankybox in 2019-2020. They were a lot better than the slop for 4-year-olds they make now.
Guess the Price is a game where Adam bought Justin various items, and Justin had to guess the price of them (and use them a bit).
In 2025, Guess the Price was rebooted, but now it is a lot more kid youtube farm esque and targeted to 5-year-olds. It is still better than their current content at the time of this being written.
Person 1: Why does Lankybox suck so bad?
Person 2: Check out their old Guess the Price (Lankybox) videos, they are a lot better

go off, I guess 

Sort of like "you do you," but with a strong implication that you're talking out of your ass. Basically "you're an idiot and what you're saying is stupid, if you want to keep going I guess I won't stop you."
Bob: "The world is run by lizard people."

Sue: "There's no such thing as lizard people, but go off, I guess."

I guess you had to be there 

What you say when someone tells you something he thinks is hilarious but really isn't. You say this to avoid hurting your friend's feelings in breaking it to him that his joke sucks.
Dudeman 1: "Oh man, I was playing horseshoes in Red Dead Redemption and I got a really close throw and John was all like, 'Did you see that!' It was so funny dude!"

Dudeman 2: "I guess you had to be there."

Dudeman 1: :(