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What would ruin your night more? Finding out the woman you just spent the night out drinking with stole $10,000 off you or the fact that she took your $2,000 Hermès ashtray? Considering that's a conundrum none of us will ever have to confront, we might not be able to sympathize with this fella Grant Gordon, as The New York Post reports.

Kelly Keiser—a 32-year-old female bodybuilder (!)—and her friend had drinks with Gordon and his friend at Lavo before heading further uptown to The Carlyle for even fancier drinks. They drove there in Gordon's very expensive car, enjoyed drinks and went their separate ways when Keiser and her friend got into a cab. Just a few minutes later, Gordon realized that not only was a $10,000 check missing from his car, but so was his $2,000 Hermès ashtray. The cops pulled over Keiser's cab, searched her bag and found the stolen property. Keiser's attorney believes that she may have been set up by her friend (who fled the scene and is still unaccounted for according to court papers) or possibly drugged.

We don't have the full story on the front of exactly what happened just yet, but I have SO many questions. The huge check? I can believe that a very rich man had such a check in his car. That's fine. But why does he have a fragile, expensive Hermès ashtray in the car? Where was it located? Was it just sitting on the floor of the car, all devil-may-care style? Was the standard car ashtray not good enough? Or did the car not have one, so he bought one of his own and opted for the Hermès? Which ashtray was it? Hermès makes so many different designs, I'd like to know. The one above retails for $1,975, for example. Though the ashtray and check were reclaimed, we just hope no such tragedy of the 1% happens again.

[Photo via Hermès]