This trope occurs when a character, brimming with overconfidence, makes a deal, wager, or agreement they think they can’t possibly lose. At first, it seems like harmless fun or even a guaranteed victory. But when the challenge begins, they discover their confidence was misplaced — and by then, it’s too late. The result? They’re bound by the very contract, oath, or bargain they so proudly entered. What was meant to be a lighthearted game spirals into humiliation, torment, or even doom and sadly for the character, still consensual. It’s the perfect storm of pride, irony, and dark comedy: the character isn’t undone by an enemy’s cunning, but by their own mouth writing checks their fate can’t cash.