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."
by yes juanito yes December 21, 2017
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An affectionate saying, usually what a mother would say to her child to express her innermost feelings.
Child: *starts fucking the cat*
Mother: 'I should've aborted you.'
by niqht May 31, 2018
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A day when every single thing seems to go wrong, like dropping thing up to bumping your head against everything.
person 1:Ouw! WTF!
person 2:what's the matter?
person 1:hit my hand with a hammer, after i hit my head against the window.
person 2:major bummer.
person 1:it's a Should've-stayed-at-home day.
by DJ MTL February 13, 2012
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A quote from Ushijima (Ushi Gushy), the farmer man. Oikawa disagrees strongly
Example 1:

Ushijima: Oikawa, you should've went to shiratorizawa.
Oikawa: f^CK NO

Example 2:

Person: Oikawa should've went to shiratorizawa if he wanted to go to nationals.
Me: i meannn... do you think he looks good in purple? (fnaf 101-)
Person: Fuckin Simp-
Me: yeah... i know
by Oikawa.Is.Flat.Asf.But.He.Cool December 14, 2020
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Seijoh's volleyball captain made a huge mistake and went to the wrong school. Smh Oikawa, smh... He should've come to Shiratorizawa, the best volleyball team ever in the whole universe...
by Wakatoshi January 8, 2017
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A phrase uttered when a rich and/or famous black person does or says something so stupid that it can be viewed as an embarrassment to the entire race. Can range from a ridiculous comment to a stupid action, or anything that helps to further the stereotypes against blacks. Often puts even-keeled blacks in the tough spot of hating some of their own, while simultaneously keeping YT in his place. If these people were not rich and famous, they would be able to exist in obscurity as the idiots that they are, drawing very little attention to themselves except for when they inevitably end up on the local 10:00 news over some dumb shit.

Taken from the Rick James episode of Chapelle's Show. Rappers and pro athletes are the most common targets of this remark. Watch 106 and Park or any major celebrity event on BET, and you'll be saying this quite a bit.
*turns to 2009 BET Awards*

*Sees Soulja Boy*

Me: "They never should've gave you niggas money!"
by hatestupidity June 29, 2009
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A shitty way to prevent embarrassment from telling a story horribly and getting a poor reaction. Usually aggravates the hell out of me.
"And then he goes to motorboat her-Ya know what, you should've been there!"
by WellFuckMyAss May 19, 2017
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