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When you blew something so monumentally that not only your entire circle of friends, but your biological family is aware of just how deeply you screwed up. Apart from the generic, the connotation of this term transcends the platonic, romantic, and sexual; especially when you allowed your partner's judgement to override basic common sense, costing you something far greater than they could ever offer. Bonus points if your losing the draw was directly analogous to a friend or, say, father's gambit.
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