Winning

An ironic display of triumph over a situation that is, in fact, partly or totally self-destructive or harmful.

Example #1: "My kid got into Harvard and it'll cost me my entire retirement savings to send them there. WINNING!"

Example #2: "I'm a reasonably decent actor with a fat bank account, but I've chased two wives and five children away with out-of-control partying, drug use and violence that's laughable for someone my age. WINNING!"

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