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What’s Your Dilemma DuJour?

The high life comes with problems, but don’t worry—we’re here to help

Whenever we’re out, my boyfriend only pays cash, whether it’s for the 1999 Pol Roger or my monogrammed Hermès toolbox. Should I be concerned?

Unless he’s going through a major divorce (aren’t they all?), chances are that, yes, he’s hiding something from someone, whether that someone is the IRS, the FBI or y-o-u. If it’s divorce, rest easy: Of course he wants his transactions untraceable, especially if he’s wooing you with Hermès. But if he’s verifiably single, or has been telling you he is, you might raise an eyebrow if you still can (ahem). Best-case scenario: He’s got so much debt he’s been blacklisted by his Black Card. Worst: He’s either dealing forged prescriptions to real housewives, minting the green himself or working for the mafia. (Although, would landing a spot on Mob Wives really be so bad?) The key is whether or not he’ll tell you, when asked, why he’s doing it. Could it be that he’s—deep breath—just buying strictly within his means? 

We pledged $50,000 to Save the Seals, but then realized we needed the money to go on safari. What’s the best way to back out? 

I totally get it: You wanted to see your name on the invitation under that flashy Platinum Sponsor flag, but now that the invites are printed, you’re not so sure. Crafty you! Before you bail, though, how about seeing if you can work out a payment plan of sorts? This situation actually happens all the time. (You think everyone who pledges big bucks to charities actually has them? Get real! It’s mostly a pissing match.) In fact, some charitable organizations say it’s not unheard-of for sponsors-in-straits to honor a single pledge over as many as 10 years. Just be sure to cite an “underperforming” stock, and understand that you’ve forfeited your holiday bragging rights. Don’t be daft enough to send your development officer a postcard from the bush.

My friend Denise is encouraging me to renounce my U.S. citizenship to save on taxes, like she did. Will I have to pay back taxes when I want to get it back later? 

Listen, I know things didn’t exactly work out as we wanted them to, but there’s no need to go AWOL entirely, “friend” of Denise. Because once you leave, you can’t come back—and if some lawmakers have their way, not even for a visit. That said, I consulted with prominent Washington, D.C. tax attorney Bradley S. Waterman, who pointed out certain provisions of the Internal Revenue Code that apply if you decide to renounce. If you’ve got a net worth of $2 million or more, better brace yourself for a large exit tax and your heirs for some potentially stiff gift taxes (up to 35 percent), but you probably won’t be able to avoid U.S. tax. And don’t even think of handing over Aunt Janie’s Matisse collection to your sister, unless you want the IRS after her, too. Although considering that bitch got all the skinny genes, maybe you do.