Who Should Pay on the First Date?

who pays on the first dateIt doesn't have to be a recession'ish time to ponder the pros and cons of who picks up the check on the first date. Two fantastic (and single) he and she bloggers took on this week's He Said/She Said question and interestingly came to a similar conclusion via different paths.

Our He, Matthew Wells, is the creator of a meandering blog of literary delight, jam-packed with obscure factoids you never knew. A Likely Story will draw you in with tales from the bar in his 100 Proof series and keep you there with the best analysis of Boobquake 2010 that you've ever read.

Liz Weber fills up The Space in Between weaving tales of a Costa Rican croc named Osama Bin Laden, online dating, and a fantastic guide to making retrograde work for you (which I wish I had read when it was happening).

So, Liz and Matthew:

Who should pay on the first date?


He Said:


Hmm. Let me give this absolutely no thought at all. My automatic answer: If it’s a date, the guy picks up the check, because that’s how you know it’s a date in the first place. Or at least that’s how you know the guy thinks it’s a date in the first place, or wants it to be. Picking up the check is a signal of intention and interest. It’s the guy saying, “I’m not just looking at you as a friend.”


But it’s also a sign of respect, in a way that has nothing to do with romance. When I say, “Do you want to go out to dinner?” and you say, “Yes,” then that means I’m paying. Why? It’s all part of the package. We wouldn’t be sitting across from each other sharing a meal if I hadn’t popped the question, and picking up the check is understood as a given the moment I hear your “Yes.” It’s not even an option. Think chivalry. 


Of course, chivalry may seem quaint and even sexist in our courtesy-challenged society, but again, it’s a sign of something. All first dates take place in a Signals Bar.  Everything I do and say will be interpreted a hundred different ways, like a speech at the United Nations. If I pick up the check, it says a couple of interesting (and hopefully interest-related) things about me. If on the other hand I say, “Let’s split it,” that says something, oh, half-interesting at best. And if I say, “So is it okay if I leave the tip?” that’s what most women call a deal-breaker.


Another deal-breaker is the guy who goes into a first date saying to himself, “I will only pick up this check if there’s a spark,” or, “I’ll pay if I think this is going somewhere other than two separate cab rides home.” This guy you do not need, ladies -- this is a sign that you are having dinner with someone who is totally prepared to dump you for somebody younger or prettier at the first available opportunity. Since his feeling is that a date is like a high-risk investment, that means he orders the wine believing that he’s owed something in return, and if he doesn’t get it, then he’ll put his money somewhere else. (This probably also means that he’s involved in insider trading, and treats his secretary like crap. Run; don’t walk.) But dating is not an investment. In reality, dating is a gamble. It’s like a game of poker -- you raise, you call, and you always pony up to see the other player’s cards. 


And, like poker, if you raise? The game continues. But if you call? The hand is over. If a woman insists on paying half, then there is no date. As a guy, if someone I’m interested in throws down a couple of 20s and says, “No, I insist, this is for my half,” that translates in my brain as, “I am not interested in you romantically.” And I’m fine with that; in fact, I’d rather hear that than the actual words, “I am not interested in you romantically,” because the actual words hurt like hell. That’s why, when a woman says she wants to pick up half the dinner tab, it’s the rejection equivalent of French: a really nice way to say something that in reality, is a slap in the face.


But -- and I cannot say this strongly enough -- it is also a heart with a line drawn through it, which is the universal symbol for NOT INTERESTED. So if I do continue seeing this woman, it will have to be as friends, unless I want to delude myself into thinking that through the liberal application of persistence and three-course dinners, I can get her emotional barometer to swing from COLD AND DISTANT to HOT AND HEAVY. And don’t think I haven’t spent years paving a road through that emotional jungle, okay?


Oh. You too? Really? 


Interesting. Want to talk about it over dinner?

She Said:

“I’m having an amazing time,” Drew said, his big, brown eyes smiling with delight. 

“Me too,” I almost giggled as I took another sip of wine. 

It had been a great first date -- one of the best I can remember. We laughed and talked with the ease of a couple dating for months, not hours. He was scoring high on the first-date checklist: Good conversationalist -- check. Great table manners -- check. Polite and courteous -- check.   

So when the bill arrived and he gently pushed it toward me saying simply, “You got this, right?” I was speechless. 

The shock of it all prevented me from doing anything other than paying the bill. My disappointment was palpable. The night was going so well! It was as if someone just pulled the plug on one of those old record players, the needle scraping against the vinyl with a horrible screech. 

“Why didn’t you say anything?” my friend demanded the next day when I told her what happened. “He invited you out, didn’t he?” 

“Well, technically he suggested we go out, but it was more of a mutual thing,” I countered. 

“That’s crazy!” My friend snorted. “The guy should always pay on the first date.” 

This got me thinking. Why should the guy pay on the first date? It’s the new millennium after all. Isn’t it a little antiquated to expect such chivalry? 

All of my friends said, emphatically, that they prefer the guy to always pick up the tab -- especially on the first date. I wasn’t convinced, so I took it to my blog, asking all my female readers to weigh in on the subject. 

    “The person who requests the date should pay for the date. If a woman asks a man out, she should expect to pay. This lends itself to the notion that if things are going well, keep it going with the counter offer. Dinner was great and thank you, now let me buy you a drink, a coffee a piece of cake.....” --F, early 40s

    “…I insisted on going dutch the first date; unless the date was precipitated by him asking: "Can I take you out to dinner," in which case, he paid…..I kept the dutch rule because, firstly, I've always been proud when it comes to money (perhaps a character flaw); and, secondly, because I believe that equality between men and women begins with treating each other as equals in everyday circumstances. If I depend upon a man to buy dinner, that dependence could stretch into other categories as well.” --A, 33

    The guy should definitely pay on the first date. I think for the masculinity/femininity balance to work out, the man has to be the provider, especially at the beginning. He has to show that he can look after her. She’ll then feel safe and be able to open up to him…We all have both masculinity and femininity within us, and to keep the chemistry alive in a relationship, you need to be mostly in the opposing trait to your mate.” --K, 41 

Here’s the thing. The very reason that I would like the man to pay is because I’m an independent woman. I work so hard at taking care of myself and holding it all down that it’s nice to have a man who wants to take you out, show you a good time, and insist on paying the bill. For me, it’s like a mini vacation or more importantly, it gives me the chance to relax a little and let someone else be in charge for a change. 

Just because I’m a strong woman doesn’t mean that letting someone else take charge will threaten my ability to take care of myself. If a person is truly comfortable in her personal power, allowing the guy to pick up the bill isn’t anything more than a nice gesture. It is just as much an act of power to receive as much as it is to give  

I say, keep it simple. If you’re interested in a second date, let him pay and offer to take him out the next time. Otherwise, politely decline and offer to split the bill.   

Either way, always remember, you’re just as much a part of the date as he is and however you feel about him, you still get to choose what’s best for you.   

I thought about it and Drew really did ask me out on that first date and my reason for declining a second one was simple. Dating, especially the first few, is all about putting your best foot forward and I’m not ashamed to say that I expect the very best from a man who’s interested in me. Drew didn’t deliver and put his best toe forward, and in the end, it’s not about the money -- it’s about the effort.

Read more from Matthew at A Likely Story, and Liz at The Space in Between.


Image via alex-s/Flickr

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