Money Manners: What to do when your girlfriend is a freeloader

Dear Jeanne & Leonard:

I make a lot more money than the woman I’ve been seeing, so about a month ago I proposed that I pay for everything when we go out. She was very appreciative, but here’s the problem: Since I’ve started paying, she’s begun ordering the most expensive items on the menu, things she never ordered when we were splitting the tab. Even though I’m doing pretty well, I’m not an extravagant guy, and it’s driving me crazy that she keeps ordering things I’d never treat myself to. What should I do here? I really like her otherwise.

— Getting Heartburn, Southern Connecticut

Dear Burned:

Tired of paying for those coconut-water martinis, are you? We don’t blame you. There’s a word for people who cavalierly help themselves to goodies someone else is paying for, and the word is “freeloader.” And, alas, leopards rarely change their spots.

Maybe, though, with one of those horrible, all night, we-need-to-talk-about-us conversations, you’ll be able to get your girlfriend to understand why her behavior bothers you and persuade her to change. But the lack of consideration she’s shown for your wallet suggests that this woman, attractive as you may otherwise find her, might not be the right one for you. If she doesn’t have an epiphany when you explain to her what the problem is, it’s probably time for you to move on.

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Dear Jeanne & Leonard:

My accountant retired, so I need a new one to do my taxes. When I asked a friendly neighbor in the small condominium complex I recently moved into whether she could recommend anyone, she told me that she and lots of others in the building use “Dan,” a CPA who also lives there. I thanked her, and the next thing I knew, I got an email from Dan proposing a time at which to meet to review my finances. Frankly, I’m not very eager to share this information with someone in the building, especially someone as pushy as Dan. But what can I tell him and the neighbor who gave him my name and keeps asking whether we’ve met yet? They both know I need someone to do my taxes, and I don’t want to brush off a person all my neighbors like.

— Pressured, New York

Dear Pressured:

In a perfect world, you’d leave out the “pushy” part but otherwise tell Dan the truth: that you feel uncomfortable about sharing your personal finances with someone so close to your neighbors. Unfortunately, he could interpret this to mean you don’t trust him to respect your privacy and hence be offended. So welcome to white-lie territory. Consider telling Dan that your boss just recommended a CPA, and you feel it would be injudicious to ignore his advice. Or tell him that your former accountant had an associate you’ve decided to try, or that this year you’ve decided to prepare your returns yourself. In short, tell Dan whatever you think sounds most credible and least critical of him.

And now you know: Never ask for a recommendation from someone whose recommendation you’d feel uncomfortable not following.