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.
by Grindin’ Jo September 28, 2018
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You missed being a part of something big. You didn't see it. You weren't there. You can only imagine, but it's not good enough, cuz you weren't there. You should have been there. It means, folks wish you could have seen it, but you didn't. And even if you could see it on video, it's not good enough. You should have been there. The energy was amazing.
Dood, you totally missed it. You shoulda been there.
by Pisgah March 07, 2012
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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.
by lil smartass wigga August 31, 2006
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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."
by Vid-szhite May 18, 2014
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Meaning: would have, could have, should have
A reply you give to a whinging person who is expressing regret for not having taken a particular course of action when the opportunity originally presented itself. They've suffered the consequences and they are possibly fishing for sympathy or simply beating themselves up about it.

It essentially means, "Too late for regrets, you can't change the past, get on with your life, learn from the experience, make better choices in future, stop doing a post mortem on your life."
Brian: If only I'd listened to my folks and hadn't dropped out of school, I could've been someone by now.
Cecil: Woulda coulda shoulda, Brian.
by suedannim March 04, 2013
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when a person has gotten burned so many times they should have already seen it comin'.
Your girlfriend cheated on you but you take her back and then she does it again and you get mad about it. So she tells you, you got "burnt shoulda learnt".
by G Gonz August 04, 2007
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