Money and dating: what are the new rules?

Money and dating can be a dicey mix.

Traditionally, women have expected men to pay for their dates, at least in the beginning of a relationship. Picking up the tab was considered to be the way men showed real interest in a woman. But now, the expectations aren’t so clear. So what’s the right thing to do when the check appears?

Let’s say you’re on a first date having dinner. You order some chicken and a beer while she orders a $12 glass of wine and salmon, which is a specialty dish. You notice that her dinner costs twice as much as yours. But after a few minutes you’re hitting it off, and are anticipating asking her out again so you forget about the cost. Then the check comes. You hesitate before putting down your credit card. You notice that she deliberately looks away and sips her wine, without offering to pay or split the bill.

Does it upset you that you’re expected to pay? Or are you happy to pay because you really like her? Do you want to ask her to split the bill?

My general rule of thumb: whoever does the asking, does the paying. If you asked her out to dinner on a first date, you should be prepared to pay no matter what she orders. If you can’t afford to pay for an expensive dinner, then ask your date out for coffee or brunch to make it more affordable. You’re in control because you’re doing the planning.

But why not split the bill? Isn’t this the fair thing to do? While it might seem the most reasonable choice, you can’t expect it. If you ask someone out and then ask her to split the bill, you risk looking cheap. However, if she offers to split the bill, you can accept. (However, I’d caution against this – she might be doing it as a gesture to be nice, but wishes that you’d just pick up the tab. If you really want to go out with her again and it’s only the first date, you’re better off just paying for it.)

Maybe you like being Prince Charming. While this is great for your dates, I caution you to not be so free with your pocketbook – you can end up feeling like an ATM machine. Here’s how to gage: do you feel like you have to keep spending more and more on each date to impress her? If so, don’t let your wallet be the center of the relationship. Try planning inexpensive but thoughtful dates instead – like a trip to the zoo, or ice skating in the park, or taking your dogs for a walk in the park along with a picnic lunch. These thoughtful gestures convey your attraction much more than a bunch of expensive dinners.

If you’re looking for a little more equality when it comes to spending on a date, let’s look at another scenario. Say you’ve been on a few dates together, and each time you’ve paid. Understandably, you want her to reciprocate. Instead of asking her to pick up the tab while you’re on a date, I would ask her to plan the next one. That way, she is in charge of where to go and what to do, and you can let her pay. All healthy relationships need and deserve some reciprocity. If she’s into you, she will reciprocate.

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