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should’ve ran the ball 

When the Seattle Seahawks were on the goal line in Super Bowl 49 they were one score away from winning. There was only a little over 20 seconds yet and the Patriots would not have enough time to score. All they had to do was give the ball to beast mode and he would’ve scored. Instead they throw the ball, Malcom Butler on the patriots defense picked off the ball winning the super bowl for the patriots. They should’ve ran the ball.
“The Seahawks almost won Super Bowl 49”
“Yeah, they should’ve ran the ball.”
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Should've-stayed-at-home day 

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.

should've used a condom 

This is a new thing people say when someone does something so incredibly stupid and disappointing to the point where the are feeling to go back im time and stop themselves from seeing that disappointment.

(Or it defines someone's child being a hoe/slut/pornstar/onlyfans creator and actually being proud of that)
Some examples of should've used a condom are:
Example 1: someone who enjoys watching skibidi toilet.
Example 2: someone who does something cringe on the internet or irl
Example 3: someone who spreads their nudes online for people to see

They never should've gave you niggas money 

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!"

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."

i should've aborted you

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.'

I should’ve swallowed you

A diss normally executed by a mother, in which she implies that when you were sperm, she should’ve given head instead of normal sex. Therefore the sperm (you) would never reach the egg and be fertilized and you would never be alive.
Son: “I hate you
Mom: “ I should’ve swallowed you”