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shoulda coulda oiled

An expression used in situations where one could have avoided a poor, destructive, or unpleasant decision by smoking hash oil instead. Kind of like the V8 commercials, except replace V8 with oil.
Guy 1: I got drunk and totaled my car last night. I feel like such an idiot.
Guy 2: Shoulda coulda oiled.

Guy 1: Man, yesterday sucked. I had to meet Jenny's parents and they totally hated me.
Guy 2: Shoulda coulda oiled.

Guy 1: I can't believe Bob overdosed on heroin. He had his whole life ahead of him.
Guy 2: Shoulda coulda oiled.
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shoulda shrug 

lacktoastandtolorant
Me : 😬

lacktoastandtolorant : shoulda shrug
shoulda shrug by intxuj March 14, 2022

Shouldabeenhigher 

A term exclusively used in Australia during the hottest 100 count down by people that typically didn’t vote themselves out have outgrown the youth radio station.
“Violent soho shouldabeenhigher…woke bastards” - explained bazza as he threw his beer at the job site radio
Shouldabeenhigher by Bat flavin January 27, 2023

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 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"

sholonda 

psycho yet sexy something something sure to rock your socks. Often a leo
Mannnnnnn i had me some of that sholonda last night and it was da fye
sholonda by Sholonda March 6, 2008

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.