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.

woulda coulda shoulda by suedannim March 4, 2013

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

Shoulda Coulda Woulda

Dismissing a something you could've done, instead of dwelling on it

"If I did _____, I would've gotten it."
"Eh, shoulda coulda woulda"

Shoulda Coulda Woulda by AstroIsOffline April 30, 2022

Would’ve Could’ve Should’ve 

Would’ve Could’ve Should’ve is a masterpiece of a song written by the amazing Taylor Swift. It is more than a song but a monologue waiting to be said, loud and clear. It is a song that describes how one her past relationships with a man who was much older than her continues to haunt her despite her ending it and starting fresh, the way it has made her lose sleep and the way it always finds a way to come back to her. She indirectly says that she regrets this in the form of poetic song lyrics whose meaning is often overlooked.

Person 1: ‘would’ve could’ve should’ve is such a good song!’
Person 2: ‘yeah’

Would’ve Could’ve Should’ve by bigbigtaylorswiftfan March 10, 2023

could've, would've, should've 

The idea of reflecting back on your life and thinking about how things might now be better if you did things differently in the past. Usually involves feelings of guilt.

"I'm always thinking about the ghosts in my past, you know. The could've, would've, should've."

could've, would've, should've by yes juanito yes December 20, 2017