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woulda coulda shoulda 

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.

burnt shoulda learnt 

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".
burnt shoulda learnt by G Gonz August 5, 2007

fuck me stupid, shoulda been running. 

Similar in meaning to “Boy, am I a dumb ass,” this advanced application of “fuck me running” is to be used in situations which were originally a surprise, but now have recurred over and over again, and the fuckee (that's you) has still not had the sense to leave.
As in: “I still have a joint checking account with my girlfriend. Well, fuck me stupid, shoulda been running."

Bitch Shoulda known 

When somebody is having a bad day and they don't take the opportunity to lay low and let the day pass by, and because of this something worse ends up happening to them.
Person 1: Did you hear that my friend Alicia failed her exam and she caught her boyfriend cheating on her in the same day, but she still decided to go clubbing later, where she ended up twisting her ankle, breaking both her shoes and had to go home early, where the taxi driver ran over her cat.

Person 2: OMG Bitch shoulda known! Stay home and let it pass if the day looks bleak.
Bitch Shoulda known by Bennyamd October 13, 2015

Pimp's Shoulda

A mang with clean shoulda's becuz they brush der shoulda's off.
Jorelle: Damn nigga you got pimp's shoulda's.
Jamal: That's how we roll in the clean norf nigga. Let's go score some crack!
Jorelle: Mos def nigga i haven't smoked dem rocks in two days! Nigga!
Pimp's Shoulda by Mack Pervert April 4, 2004

been shoulda been 

Should have already done so prior to already doing so.
He been shoulda been payin’ me my money!