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Dating After 50: Who Pays for the First Date?

Who pays what is particularly awkward in the beginning of a relationship, especially at the first meeting. You don't know each other at all and you don't even know whether there's a spark between you, so most people don't talk about money, and the guy usually foots the bill.

But if the meeting might progress into a relationship, you have to figure out the money plan pretty quickly. Otherwise, misunderstandings may end the date before it has a chance to grow into something else.

The first meeting

It's almost axiomatic: The man pays for the first coffee or casual get-together. If you want to change that tradition, you have to do it in the most gracious way possible. You have a few choices, and all of them are risky.

For example, if you're a man who doesn't want to pay for all these first meetings, you can just say to your date, “I'm all for men's and women's equality, so I like to split all bills. Is that okay with you?” A traditional woman may write you off, but a more modern one may chip in without a second thought.

But be warned: Even feminists like to see a little gallantry at the beginning. Perhaps you only want to make this move if you're not totally enchanted with your date!

On the other hand, if you're the woman in this situation, the offer to split the bill will give you plenty of points with some men. But if he insists on paying, let him. Otherwise, he may let you help pay but feel like you're too defensive or strident to pursue further.

Don’t let your first coffee be your last

If you aren’t careful, your first meeting for coffee with a prospective date could be your last. Consider this example from Barney and Leigh:

Barney felt strongly that if women wanted to be treated as equals, they should pay as equals. His first coffee with Leigh was going so well that they had a second and then a third coffee, and then the coffee date lengthened into the early evening, so they ordered some appetizers. At the conclusion of this promising beginning, Barney said, “How about we split this?”
Leigh, a professional woman, felt rather stung that her date wasn’t going to cover what was ultimately, in her opinion, a fairly inexpensive bill. She was obviously hesitant about it, and so Barney challenged her on her feminism. Saying something like, “I presume from our conversation about your career that you believe in women’s rights, and I’m very supportive of that — and so I assumed you would be comfortable with splitting 50/50.”
Leigh was surprised at how she felt, but she felt he was being cheap and provocative. She forked over her credit card with obvious disgust, saying, “No problem,” but her body language and tone made it clear she wasn’t happy with the way things had turned out. Both of them walked away from the table irritated and pretty sure that they wouldn’t be seeing each other again.
But perhaps they were fated to have a second chance. They met again at a gathering for a local political candidate, and after a chilly beginning they relaxed, talked again, and with much good humor recounted their initial feelings about the “check fiasco.”
They started going out again after that and are still together. Perhaps “all’s well that ends well,” but most people don’t get second chances. Point to be taken: Don’t complicate the first coffee by letting money become an issue right away.

The issue of paying more equally is a lot easier for both men and women on a second meeting for coffee or the like. You're not on a date quite yet, but you've both signaled the desire to know each other better. Offering to split or take care of the second coffee is more likely to be seen as just a nice or fair thing to propose.

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