The Pricey-date Problem

You’re smitten with the new person you’re seeing—but he’s a big (too big!) spender. What can you do before you go broke?

By Stephen F. Milioti

our first date went pretty well, but it was a little extravagant for your taste. The guy picked a dinner spot that cost you nearly $100 (including overly-expensive wine). But you figure, It’s not a big deal, he was just trying to impress me. The next date, though, he proposes that you both go to a show, letting you know when you show up that the ticket is $90, which you give him at dinner, plus another $100 for that meal. Now, even though the guy’s cute, the financial commitment is getting uncomfortable. Even if you’re doing pretty well for yourself, you probably don’t like hemorrhaging cash this way. So you may wonder… should I see how long I can keep up with Mr. Big Spender? Or should I end things now, before the credit-card debt piles waaay up?

A closer look at dollars & dating
“The issue of spending a lot of money on dates really touches on the essential values that
Have the talk without becoming confrontational.
people have regarding finances—some people see money as the only way to express love, interest and fun,” says Rik Isensee (, a psychotherapist based in San Francisco, CA, and author of books including Love Between Men: Enhancing Intimacy & Resolving Conflicts in Gay Relationships. But he also cautions that you should wait two dates to make sure this is an actual recurring problem, not just a well-meant gesture. “At first, your date might be wanting to do lofty things just to impress you,” he says, “so don’t automatically take it as something that’s meant to alienate you. It might just be his way of wanting to celebrate his newfound interest in you. It’s normal for someone to go a little over-the-top on the first date.” However, says Isensee, “if the big spending goes on longer than the first couple of dates, and you’re uncomfortable, you’ve got to speak up—otherwise you’ll build resentment toward the other person.”

How to have the money talk
OK, so you have to bring up the impact that dating this person is having on your wallet. Isensee recommends that you couch it in the positive, to avoid coming off as unnecessarily confrontational. “Sit down with the person,” says Isensee, “and start out by saying, ‘Hey, we’ve done some fabulous stuff on our first couple of dates. And I love expensive dinners as much as the next person. But I’d like to spend a little less in the future—so how about a nice long walk next time, followed by a dinner at a fun place that’s a little more moderately-priced?’ Offer a concrete, solid option like that.”

If you speak honestly like this, your date might respond with relief: Charles, 34, a waiter/actor in New York, NY, says, “It’s embarrassing to admit, but I’ve gone into a little credit-card debt, spending too much money on the first few
If he reacts negatively to your request, that’s a warning sign.
dates with guys. I think I’m trying to show I’m successful, that spending $80 on dinner isn’t a problem for me. I’d be so relieved if a guy told me up front, ‘Let’s not spend a lot of money on a date.’ I’d put my bowling shoes on and have a lot more fun.” Suggesting this compromise (still a good dinner out, just not so expensive), instead of a $1 hot dog, shows that you’re open to nice things, but just don’t want to spend a whole paycheck.

Understanding how your date reacts
How your date responds to this discussion is critical. Unfortunately, this part didn’t go so well for Robert, 37, a merchandising executive who lives in Chicago. “I recently got into a situation where I started dating someone I liked, but he wanted to go out and spend hundreds of dollars on every date—from theater tickets to dinners and so forth,” he says. “He didn’t pay for me — nor did I want him to — I have a good income. I just don’t believe in dropping so much money on a date. So I told the guy how I felt, and to my shock, he said I was boring, and he wasn’t interested in someone who doesn’t enjoy the finer things. I was hurt, but at least I knew where things stood!”

As surprised as Robert was, though, his honest way of handling the situation saved him early on from a major mismatch. “Heavy spending isn’t necessarily the huge problem,” says Isensee. “If you confront your date about it, he could very well see your point, admit he was just trying to be impressive, and strike a compromise. But if he reacts negatively or defensively, or judges you, that’s a huge problem—a sign that you should probably break things off. Because at that point, he’s not respecting your feelings on the subject. And it’s your money—you make decisions about it.”

The good news is that, if you bring up the money question and your date responds respectfully and agreeably, you’re well on your way to smoother dating: “If you’ve agreed to a general price range and have similar interests, you’re set up to have lots of fun,” says Isensee. “If there’s a connection — and passion — you don’t have to spend a lot to enjoy yourself.”

Stephen F. Milioti is a New York-based writer who has contributed to New York and
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