Ask Wendy

What’s the Etiquette For Paying For Dates?

Friday, April 13, 2018
couple drinking wine on date
Hey Wendy,

I used to have a hard time letting guys pay for me and take me out. I used to attract men who wanted me to go Dutch, or even pay for them. This was a turn off for me. I’m a successful and independent woman and I don’t need men to pay for me, but it does feel really good. It puts me in the feminine. I enjoy it.

I’m dating a great guy who is used to women splitting the check but will pick up the tab, as I’ve expressed that I like being taken out. But I have this nagging unpleasant feeling inside of me when he does. I feel guilty or as though I’m a “gold digger.” I’m still not quite used to this. (I have taken him out to dinner once and will get him small gifts).

Does the guy always pay?

I would love to hear your thoughts about money matters while dating. It is so confusing to me.

Monisha L. – New York, New York

Hey Monisha!

First, congratulations on graduating from dudes who don’t pay and/or expect you to pick up the tab. Girl, that is not okay. Say it out loud with me: “I don’t pay for men on first dates. Never again.”

Here’s the deal with paying for dates:

Men get burned out buying a string of dinners, drinks, movie tickets, etc. for strangers who feel entitled to it, act ungrateful, and then never want to see him again.

Women feel diminished, disrespected, and not special when a guy doesn’t treat. And she’s often left calculating her losses where the time and money she put into looking nice for him are concerned.

It’s a conundrum.

My solution is to try and make the first meet-and-greet date either free or very low-cost, like coffee or a tasty adult beverage at a nice but not bank-breaking bar. That way, if they offer, you can gracefully accept and not worry about cleaning out his pockets.

Based on your preferences (which are most women’s preferences, btw), don’t be the first to offer to pay. Don’t pick up the check, don’t even look at the check—just be in the moment with him. It’s uncomfortable, I know. Don’t do the fake-purse-grab that we’ve all mastered. Just wait. And when he picks up that sleeve, keep waiting…until he says, “I’ve got this!” If he doesn’t say anything, and he’s tentative or just holding it, you say these three words:

“May I help?”

Whatever you do, don’t say, “What’s my half?” or “How much do I owe?” or “Will twenty cover my part?” None of that nonsense.

“May I help?” is what you say. Nothing more, nothing less. This leaves it totally up to him. Ball in his court. Is he going to treat, or is he going to tell you what your half is? Maybe you get to pay the tip. Also, “May I help?” doesn’t imply you’re picking up the whole tab. “May I help?” is a partner question. It’s like you’re saying, “If you treat, that would be delightful. If you need me to contribute, I’m right here to do that, my friend—whatever you need.”

When they say, “I’ve got this”—and the new guy(s) you date will do that—then that’s your big chance. Thank him. And I mean really, genuinely thank him. You could thank him for the entertaining company he’s provided, or the delicious meal or drink you consumed, or for the ambiance of the spot he picked if he chose the place. But don’t thank him for the money. It’s not about the money for him. It’s about treating you to a high-quality date, and that’s what you want to appreciate him for.

Now that you’re dating, it sounds like you’ve got this. You’re picking up the occasional check and that’s sweet; it shows you’re not expecting a free ride. But I don’t want you sitting in that uncertainty, I want you to do something about that. This sounds like a crazy idea, I know, but I double-dog-dare you to do it. Be vulnerable. Talk to him about it. It’s this simple: Either the next time you see him or after he takes you out again, right after he pays, say something like this:

“Hey, so I want to really thank you for treating tonight. The food was amazing, and we had such a great conversation about ___. I do feel a little funny about it, though, because I don’t want you to think I’m using you or anything. But I also want to say that every time you treat, it makes me feel special, so thank you for that. How are you feeling about it? Does the way we do things feel unbalanced to you?”

Scary, right? I know! But I have faith. You can do it! And he will appreciate it, because you are giving him the opportunity to speak up, and also the chance to see how you resolve uncomfortable things that come up in a partnership from time to time.

When my guy and I started dating, he was going through a California divorce (that means paying for two houses instead of one), and it took him a moment to calibrate to that new situation. He still wanted to pay. I still wanted him to pay. But it seemed a bit off. And like you, Monisha, I didn’t want him to think I was a gold digger. So, I had that scary, vulnerable conversation. Over time, when we’d been dating for a while and it was clear to us that we were good together, we opened a joint checking account. I put a small amount of money in it each month, and he used that ATM card to pay for some of our dates. Now—if you totaled up the whole courtship tab, he paid waaaay more than I ever did. But that small amount helped, and it felt like I got to contribute just a little while he was still “treating” most of the time. Clever, yes?

If I had it all my way, men would do most of the treating and women would pick up things here and there, like the coffee or ice cream after dinner, or the picnic lunch, or even throw half down from time to time, whatever. Plus, we can contribute in other ways, because there really is something to feeling chosen, and like you matter to him. We put in a lot of effort when we prepare for a date, from manicures to hair to outfits to waxes to a million other little things. There’s something about a man paying that says, “I appreciate and honor you.”

Now, for any woman who is reading this thinking, “This is bullshit. She’s setting us all back. I like to pay!” then cool, this one is not for you. Keep pulling out your credit card, you do you. If you like that feeling and it’s important to you, I don’t think you’re doing it wrong. People get to want what they want and make decisions accordingly. Monisha and I want a delicious meal, and we want our guy to take us out for it.

Happy dating!

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