He Asked Her to Pay on the First Date

Hi Terry,

I went on a first date yesterday with a guy I met online. We met for brunch, and it was nice. A little awkward at first but after an hour or so we both relaxed. We decided to then head to another cafe for coffee where we sat on this comfy sofa and drank coffee and listened to French music. We stayed there chatting and relaxing with each other, and the next thing I knew, it was dark outside.

So we decided to go to a local wine shop. I bought a bottle of wine, and we took it back to his apartment. Dont worry, I didn't sleep with him. We simply drank the wine while listening to to his music collection and looking at photos from all his extensive travels over the world.

At this point, we'd been hanging out for about 8 hours! A new record for both of us. We clicked and felt really comfortable with each other. We talked about everything, family, NYC, friends, food, music, you name it. During the time at his apartment we shared our first kiss. It was nice, and I was enjoying myself. So we decided to go get dinner. We went to a little Mexican spot near his place, and we had a couple of margaritas and awesome food.

Now here is the problem. When the bill came, he asked me if we could split it. I've never paid for a first date and always believed the guy should pay for it. That's how its always been. I acted cool and just said, "Sure!" In the end, he did pay for the entire bill because the restaurant was cash only, and I only had a credit card. Now I'm confused about this guy and how I should proceed with him, if at all. Should I tell him that it bothered me that he asked me to pay? Should I let it go?

I liked him but I'm not sure how to feel about a guy who doesn't want to pay for the first date. Any advice would be greatly appreciated. I spent a total of 12 hours with this guy on a first date, and everything was great except this one little part.

Thanks so much, Terry!

-Reluctant

Dear Reluctant-

I'm not sure why the guy asked you to pay for dinner, but you're right to be turned off. As you know, I'm all for equality of the sexes, but men tell me (the normal ones, anyway) that they expect to pay for a first date. They also say that when a woman offers to pay, it leads them to believe she's not interested.

I would have serious reservations about continuing to see a man who didn't offer to pay the first or even the second time around. As I got to know him better (and felt we were on surer ground), I'd be glad to offer to pay for dinner or drinks on occasion. In fact, I'd feel very good about it.

But back to you:

It sounds as if you packed three dates into one. It's great that you felt you hit it off, but the best course of action would have been to say "Thank you and nice meeting you" after brunch. (I hope he paid for brunch.)

Instead, you bought wine and went to his apartment, which was a bad idea. For one thing, you met the guy online. You broke a big safety rule here; you cannot go home with strangers. From now on, meet men you encounter online in public places. Stay in public places until you know them well enough to do otherwise. You don't get into their cars, let alone go to their apartments.

(You write, "Don't worry. I didn't sleep with him." No, but you did jeopardize your safety. Please give this serious thought.)

You don't mention if he made a move when you got back to his place (other than the kiss, that is), so I don't know what his intentions were. If he made the move, and you resisted, he may have decided not to invest any more money in the encounter.

This would show him to be cheap and pathetic.

If he makes contact, I wouldn't mention his request that you kick in for dinner, but I'm pretty sure I wouldn't go out with him again, either. If you do decide to give him another chance, be prepared. He's probably going to ask you to pull out your wallet.

The next time you meet a man with potential, please remember a rule of human nature: People want what they can't have. So keep your dates short (in other words, keep a man wanting more). Keep your dates public. Don't call the guy afterwards. Let him call you.

I'm not an advocate of waiting by the phone or holding up your life in the hopes that some prince will rescue you from your perfectly fine life, so stay busy and happy. Let him decide whether he's going to step up and prove himself worthy of your attention.

In the meantime, don't be hard on yourself. We all make mistakes.

Should a Guy Pay For the First Date?

A couple of readers asked me this one.

I answered via my e-newsletter that, yeah, the guy should pay the first time out, only because most men will assume you're politely giving them the heave-ho if you reach into your wallet.

Unfortunately, this means that men can shoulder an unfair financial burden. So, if you're out for the first time with a guy, and you like him, let him pay. Then look him in the eye, smile sincerely, and thank him. You can say, "What do you say we let me get it next time?"

This way, he knows you like him. He knows you are not taking advantage of him (a lot of men have been burned by women who feigned interest in an effort to score free drinks, for example, although I know for a fact you are not one of them).

If he likes you, he'll call you again (don't call him; you've made your intentions known). Suggest something affordable and pick up the check.

My advice solicited a question from another reader who said she went out with a guy she met on a dating site. As she approached the register to pay for her meal at an Italian buffet, the guy, who'd already paid for his, gave her an annoyed look. He asked her if she expected him to pay.

She said this pretty much 'screamed' to her that he didn't like her even before they'd eaten lunch. She asked if I agreed. I agree. It's possible that he was protecting himself from being taken, but come on. What a turn-off!

Next.

And if he ever called again, I'd tell him thanks but no thanks.

If a guy's hitting dating sites and meeting several new women a week, it's going to get expensive if he pays for meals. If you agree to meet a fellow you met online, save yourself the trouble of a potentially awkward situation. Suggest you get together for coffee.

Then, if he turns out to be a graceless jerk who balks at paying for yours, tell the clerk you'll take it 'to go.'