shoulda 

Short for "should have".

You shoulda done it.

shoulda by Fangsta March 17, 2003

shoulda 

How stupid people spell "should've". Supposed short form for "should have".

I shoulda paid attention in school

shoulda by LokiBrot January 11, 2019

"Shoulda Rolled" guy 

A person that gives unwanted and unsolicited advice while he watches others play a game he is highly proficient at.

Coined by Egoraptor of Game Grumps when playing Super Smash Bros, warning his viewers that he was only playing for fun, and that savvy players should avoid microscopic critique of his play in the comments section. It happened anyway.

Player 1: (Makes a common mistake)
"Shoulda Rolled" Guy: "You should've rolled."
Player 1: "Shut the fuck up and let me play."

Egoraptor: "He had this whole essay of advice and even offered to train me."
JonTron: "Wait, seriously!?"
Egoraptor: "Ugh, I just KNEW there was gonna be one of those people, a fucking 'Shoulda Rolled' guy."

"Shoulda Rolled" guy by Vid-szhite May 18, 2014

Shoulda Stayed Down, Chack! 

A phrase used when someone does something stupid, or something goes wrong.

Person 1 trips over.

Person 2: "Shoulda Stayed Down, Chack!"

Shoulda Stayed Down, Chack! by whiteShadow00 June 14, 2009

Shoulda Bag

Shoulda Bag refers to a top in homosexual intercourse. This comes from the semblance of the bottom participant wearing a shoulder bag. More specifically when the top has their arm wrapped around the bottoms shoulder like said style of bag.

Yeah, Tony was wearing Dean like a Shoulda Bag last night.

Shoulda Bag by Grindin’ Jo September 28, 2018

shoulda coulda woulda

Meaning that it is of no use to dwell on what should have (shoulda), could have (coulda) or would have (woulda) happened/been done.
Said as an attempt to shorten a discussion that focusses on the past, thus providing no solution to an actual problem.

"Man, if only I didn't cum straight in the air, I wouldnt have jizz on my mullet now."
"Shoulda coulda woulda. There are more important things than that. There is more to life than the jizz on your mullet. You're still young, someday you will wash your hair and the jizz will be gone, but your mullet will last forever."

shoulda coulda woulda by bumarse October 17, 2009

shoulda woulda coulda 

having an opportunity and not taking it, thus regretting it later; usually used when someone is saying to the person who missed the opportunity.

Tom," man, I should have bought that car!"
Jerry," shoulda woulda coulda, but didn't."

shoulda woulda coulda by skyebrenna January 18, 2012