To fail miserably. To bomb something. To screw up. To think you're cool and just end up getting booed of the stage and realize you're not really that cool, at all. Derived from The Situation's failure at the Roast of Donald Trump.
Guy 1 - "How do you think you think you did on your driving test?"
Guy 2 - "Oh, I didn't study. I probably Situationed it."
Guy 1 - "At least you're skin isn't orange."
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