Top Definition
When you are totally trying to be nice to someone, but you fuck it all up.
"He fixed Ginger's skateboard, for free from what I hear."
"Ginger can't skate anymore, she's in a wheelchair!"
"You didn't let me finish- from what I hear he left it on her back porch as a surprise."
"That's how she ended up in a wheelchair? What a Gilligan!"
by Trans-AmIam November 02, 2017

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"Dunce Cap Redemption" is the art of still managing to hook up with someone despite an obvious injury on your face, mostly likely occurring after a night of drinking. For example, a black eye from falling, or your best friend punching you. Or a head injury from getting scraped by a wall or tree branch. It requires great courage to express interest in a girl knowing she's looking at the stupid-ass self inflicted marks on your face, and winning her over in spite of looking like a dumb asshole is a significant event. It doesn't wash away your recent stupidity, but it sure does increase your confidence.
Bro #1: "Bro, is Justin really going home with her despite that gnarly wound on his face?"
Bro #2: " Dunce Cap Redemption at its finest".

Bro #3: He's still a dumbass though"
by RickyGotWords July 30, 2017

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