shoulda bought a honda 

When somebody makes a stupid decision that they thought was right, but wasn’t their sarcastic friend tells them ‘shoulda bought a honda’ as something to say when they made the wrong decision

Man: I just bought this new car, but on the second day I had it, it broke down. Maybe I should have just listened to you!

Friend: I know! Shoulda bought a Honda! That’s whatcha get!

Man: Nah Honda’s aren’t my type of car— maybe a Chevy Impala would work out this time!

shoulda bought a honda by SlangKing3200 November 30, 2017

Shoulda Doubled Down 

You really shoulda doubled down, man

Me: *wins game of blackjack and doesn't double down*
Literally everyone in the room: "Shoulda doubled down, pussy"

Shoulda Doubled Down by instant_taco_machine May 17, 2020

shoulda lean 

well, no one really knows WHAT in the hell a "shoulda lean" is, so WHY in the hell is it the name of another goddamn rap song?! SERIOUSLY?! o well. that's ebonics for you. don't ask ME. im just bout the biggest wigga that ever existed, bra. ya feelin me?

Let me see ya bounce right to left
n let ya shoulda lean (let cha shoulda lean, jus let ya shoulda lean)
ay get it right 2 step, and let ya shoulda lean
(let ya shoulda lean, jus let ya shoulda lean)
Let me see ya bounce right to left
n let ya shoulda lean (let cha shoulda lean, ay letcha shoulda lean)
ay get it right 2 step, and let ya shoulda lean
(jus let ya shoulda lean, let ya shoulda lean)

lyrics courtesy of google. das rite. stuff that up your pipe & smoke it.

shoulda lean by lil smartass wigga August 31, 2006

Shoulda Had a Juul 

A phenomenon which occurs when one becomes intensley cross-faded to the point of becoming sick. Symptoms include sweating, pale skin, and lead to vommiting. Occurs typically when an individual becomes mildly intoxicated, and then proceeds to unexpectedly smoke more weed than their body is typically accustomed to.

“Yo did you hear what happened to Timmy last night?”
“Ya bro, he got super crossed and threw up everywhere!”
“Damn dude, he Shoulda Had a Juul.”

Shoulda Had a Juul by PatPat Patterson June 12, 2018

Shoulda Rolled

A response to something that happened that in no way could be avoided.

Police officer: The victim was hit by an oncoming car. It was going too fast for him to avoid it.

Police officer 2: ....shoulda rolled.

Or

"Today we will discuss the ways Freddy Murcury could have avoided HIV. Number 1..... shoulda rolled"

Shoulda Rolled by Pandeer Glepstein July 10, 2018

shoulda put something on the end of it 

should’ve used a condom.

bob- “i had sex with kaz the other day, i think she might be pregnant”
kim- “shoulda put something on the end of it.”

shoulda put something on the end of it by ghxstz February 12, 2023

Shoulda sat there and ate your food 

you should have shut up instead of opening you mouth to say something I was gonna shut you down to.

me: says smth
tom: thats why ur grades are low
me: embarassed cos he said the truth\
tom:... yea... shoulda sat there and ate your food...

Shoulda sat there and ate your food by don@MIT December 5, 2023