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#WhoPays: Who should foot the bill on the first date?


It’s hard to know the rules about who pays on a first date anymore — which can make for some very awkward moments.

My 23-year-old daughter recently came back from a first date with some questions about what happened when the time came to pay for the evening’s food and fun.

She had agreed to meet the young man at a high-tech driving range, restaurant and entertainment complex. Their first stop was the miniature golf course.

The cashier asked whether he should ring them up separately. There was a pause. My daughter said she was thinking that he should pay because he asked her out.

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After a few seconds of silence, the young man broke the awkwardness and volunteered to cover the charge for the two of them.

After mini golf, they decided to get something to eat. When the bill arrived after the meal, there again was an uncomfortable pause.

“He looked at the check and sighed a few times,” my daughter said. “So I offered to pay.”

The guy quickly and happily accepted. He was grateful even.

Still she was disappointed he took her up on her offer. “I wanted him to want to pay,” she said. “Or at least not make me feel bad for wanting him to pay.”

To clarify, my daughter said she’s sympathetic about the cost of dating. For her, it’s not about a man spending a lot of money on her. She just wants to be courted — her word not mine.

Yet this modern-day millennial is conflicted. Old-school tradition dictated that the guy paid as part of a chivalrous romantic courtship. New-school thinking is that such chivalry can be condescending.

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Still, my daughter said she and her single girlfriends want to be wooed at least for the first few dates. And guys show their interest in treating them special in part by paying for the date.

Over the past few years, Match, the online dating site, has surveyed about 5,000 singles to get their take on various dating habits. In its latest “Singles in America” survey, Match found that 91 percent of women think the man should insist on paying on the first date.

My daughter asked my husband and me what we thought was appropriate. Admittedly, after nearly 27 years of marriage, we have been out of the dating game for quite some time. Nonetheless, here’s our advice to her on the first-date funding dilemma.

If you’re asked out, your date should pay. Most etiquette experts suggest this as a good rule of thumb for a first date. When you ask someone out, you’re inviting the person to be your guest. And guests shouldn’t expect to pay.

As old-school parents, we agree with our daughter on who pays. We like the tradition of starting off a possible relationship with a little chivalry.

Admittedly, this rule gets complicated under the current dating norms, where women are just as likely to be the ones doing the asking. So you might want to share your views on being courted with potential suitors to establish your expectation that you want to be the one who is asked out, not the other way around.

If you’re asking, pick a date you can afford. If the expectation is that you’ll pay, then choose an outing that you can afford without asking your date to contribute.

There is nothing cheap about dating within your means.

By the way, I hear from my daughter that some women — not her — are offended if a guy uses a coupon on a first date. Their assumption is that their dates don’t think they’re worth paying full price.

Nonsense. Why do you care if a Groupon subsidized the date? I would think the person was being financially resourceful, a trait that makes for a great lifetime partner.

But because it is a first date and you don’t want your frugality to be misjudged, privately let the server or cashier know you have a coupon.

Avoid a split-the-check showdown. Don’t engage in the pretense of a fake reach for the check. Don’t offer to pay just to appear polite. And certainly don’t do this as a test to see if your date will reject your offer.

If you graciously offer to cover your costs, don’t hold it against your date if he or she accepts you at your word. You ought to mean what you say. So be sure when you accept a date that you, too, can afford where you’re going, just in case you’re asked to split the check.

It’s hard to talk about money, particularly on a first date. But this can be a good communications exercise. If you have certain expectations of who should pay on the date, try to fight through the awkwardness and just tell the truth. If it doesn’t go well, you’ve at least weeded out someone who isn’t your money soulmate.

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