Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

There’s No Such Thing As A Free Lunch

This is not a new topic, for me or for anyone else.  But it keeps coming up. And maybe now that our entire financial system is collapsing and so many of us have less disposable income than we used to, it’s an even bigger issue than before.  I don’t know.  I just thought it’d be good to address it head on, instead of as part of another post.

It kind of does matter who pays.  Or if bills are split or if you take turns paying.  It does.  I don’t know if it should, but it does.  And I don’t know if this cuts across demographics.  Is it different for people in their early 20s or daters in small towns?  How the hell should I know?  I’m no expert.

I can tell you what I know about me, and how has and can affect my life/relationships.

It turns out that for me there’s really no black and white on this issue.  Just a lot of gray.  A whole lot of gray.  I approach each date, each guy differently, because each situation is different.  Not everyone earns the same amount of money.  And I live in , a city where incomes vary wildly.  One week I might be dating someone who has to borrow money from his friends and family to pay the rent.  The next week I could be dating a guy who owns his own townhouse(No, I’m not exaggerating.  You should know by now that I have no need to make shit up.)  The amount of money a guy has or makes doesn’t interest me.  In fact, having too much is likely to be a turnoff as guys with a lot of money seem to not be able to keep themselves from bragging and that makes me not want to be around them.

The point is, I’m not going to let some broke guy spend his money on me.  I will, however, let Mr. Moneybags pick up the check almost all of the time.

You’ll note I said almost.  That’s right.  Almost.

A few years ago I went out with this guy for about a month.  He had money.  I don’t know how much but I do know that his apartment had to cost at least 4K a month*  (probably more) and by googling him I knew that he owned a successful business.  So I knew he had a lot more than me.  Back then my feelings about money were slightly different.  Men with money could pay all the time.  I didn’t feel weird about this (go ahead, write the nasty comments).  I realize the idea that the guy pays is anachronistic and anti-feministic or whatever.  I don’t care.  It is what it is.  Two people spend time together.  One has lots of money, the other doesn’t.  The one with lots of money pays.  That’s the way I see it. Well then I ended things after a month because he was kind of arrogant and some other things that I don’t need to go into here.  And he sent me a rather nasty email saying rather nasty things (dontcha love those?).  Among those was that I was a horrible person for never paying for anything.

He was sincerely offended that I’d never offered to pay.  Or maybe he wasn’t.  Maybe he just wanted to make me feel bad and thought it was something I might feel bad about.  It did make me think.  I realized that by never paying I was tipping the balance of power and responsibility in a way that I didn’t want it tipped.

So now, even if a guy has lots more money than me, I pay sometimes.  And some things I will always pay for/never let him pay for.  If we’re eating take out at my apartment, for example, I will pay for it.  I have had several guys try to pay the delivery guy and I shut them down.  It’s my apartment – I pay.  And I will NEVER let a guy give me cab fair to get home (eew), I don’t care how expensive the trip is or how broke I might be.  And then, additionally, I will make sure that I pick up checks sometimes (again, we’re now working on the assumption that I’m dating someone who has/makes more money than me).  Sometimes I will invite the guy out to some of my favorite (not expensive) places knowing specifically that I will pay.  Because I want to feel like there is some kind of balance or attempt at balance in the relationship.

I have dated men who earn less than me. When that happens I pick up a lot of checks. A lot.  But I try to do it subtly.  Then, I work on the theory that “you ask, you pay”.  So if I ask him out to dinner (my choice of restaurant), I pay.  He asks (his choice), he pays.

You’ll notice I haven’t mentioned splitting checks.  I hate going dutch.  Hate it.  I’ll do it if I’m with a guy who’s really into the who “equity” thing.  But it drives me nuts.  Friends split checks.  Not lovers.  Yeah, go ahead, call me names. That’s just the way I feel.

As for first dates, well, I usually do have the guy pay.  Because he usually grabs the bill.  But then, I’m a supercheap first date.  I frequently drink nonalcoholic beverages, even at bars, or if not just one real drink and then a switch to water.  I want to be super sharp and I’m a lightweight.  Sometimes, especially if the guy seems like he might not have much money, I’ll show up early and pay for my drink before he gets there (most of my first dates are at bars).

I titled this, “There’s no such thing as a free lunch”.  No matter how much we wish it didn’t, money does affect our relationships.  When a guy starts to spend a lot of money on me (taking me to expensive places, which is always his choice, btw) it puts stress on the relationship.  Or on me.  Maybe it shouldn’t, but it does.  That meal does cost me something.  Maybe not monetarily, but something.  And so then I take him out to brunch the next day, or to a less expensive place for dinner a few days later to try to take the stress off.

Let’s face it, dating is complicated enough without worrying about who pays.

*he lived in a building of “luxury rentals”


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14 to “There’s No Such Thing As A Free Lunch”


  1. cjw666 says:

    I agree with most of what you say and I can see how it affects you (emotionally at least). I also like the idea of the inviter pays, not the invitee (if there are such words). Furthermore, I too HATE the going dutch thing – but other than all that, as a matter of common sense, I can’t see it matters a damn who pays. If a guy thinks spending money on you (a little or a lot) gives him rights, then it should only be in HIS head and it serves him damned well right if he wastes it!

    The other thing you mention is that guys with plenty of money tend to brag about it. If they boast about it, they ain’t got much, honey! (It’s often the same in other departments too). I recall my daughter watching a youngish man parking his Porche some years ago and carefully checking it was locked, or whatever. Her comment was, “He’s not half as rich as he’d like to think, he’s too worried about the car.” It was a joke, but she was right. Real men don’t think of money as more than a tool and genuinely wealthy men don’t feel the need to be ostentatious and show off their wealth.

    Still, maybe that’s just my opinion (and I know I’m odd) :)

  2. starangel82 says:

    I operate on the first date, the guy pays, but I always offer to split. I am always prepared in the event that he says yes, but so far not a single guy has taken me up on that offer. After that, I operate on the you ask, you pay rule. I’m not a fan going dutch. I don’t mind it, but it does have a certain overly friendly feel to it. Oddly enough, I don’t mind it at the movies. Like a you grab the tickets and I’ll go grab the popcorn type thing.

    Money in relationships is a tricky thing. Not just in dating, but in committed relationships as well. I read somewhere once that biggest cause of marital disagreements is money. Whoever said money is the great equalizer has apparently never been on a date (or married).

  3. bobbyjensen says:

    The most important thing I have to add to this post is: leave it alone-let it stand by itself!
    This is the first description (that I’ve read or talked about with woman in person) that gives me the information that I want. Honest, no punches pulled, well thought out and expressed. There is no doubt as to how you feel, and neither can there be in anyone’s mind who reads this.
    As someone, you, who I believe to be a very good writer, I am going to claim this post as your best work!

  4. terrablack says:

    It’s so funny that you write about this because I was talking with a girlfriend earlier and she said, “I can’t afford to date right now,” she mentioned trying to guess who’d pay and wanting to make sure she had enought to cover herself “just in case”.
    I agree with you in that whoever asks should pay and I don’t mind picking up a tab once in a while, but the last date I had the bill sat on the table for almost 20 mins before I asked the waiter to split it and I left…never spoke to/saw him again.

  5. SINgleGIRL says:

    -cjw666
    I mean a whole range of things when I say brag. It can be, talking endlessly about extravagant trips he’s taken, chat too much about ppl and places that only a wealthy person knows about… So it’s not so much overt bragging but the subtle things that sometimes guys do to say, “I’m a great catch”. And that annoys me.
    -starange182
    I like your example of the movies. I’ve done that too. It works great if one person grabs seats and the other snacks, but it depends on the guy etc. You’re right, it doesn’t get any easier in committed relationships.
    -bobbyjensen
    Thank you so much. I don’t know about “my best” but I’m glad it was helpful.
    -terrablack
    Ugh. I’ve had those check sitting there moments. And I totally understand the not being able to afford to date thing. Seriously, the nuances of this stuff are hard. I don’t think most non-daters realize how much thought and angst we have over it.

  6. jk228855 says:

    I agree with the invitee being the one who pays too, although I never not offer to pay my share. To me, money doesn’t really matter but it is a big issue for a lot of people. I don’t think there’s anything wrong with paying once in a while, especially if you’re the one doing the asking out.

  7. recklessstudio says:

    Simply put, I will ALWAYS pay on the first date. No questions asked. After that, I would like to see an ATTEMPT to want to pay for SOMETHING. Maybe, she’ll pay for drinks and I’ll pay for the meal or I’ll pay for everything and she’ll leave the tip. Most of the time, I will want to pay and other times I’ll let her pay.

    As long as I can see an effort after the first date, that’ll at least tell me that she wants to take part in an aspect of our growing relationship – which down the road can be VERY important.

  8. cjw666 says:

    Oh, yes. I get what you mean and I can understand what annoys you – don’t always be too hard on the guys though, because, as far as they know, they have but one chance to impress you and, until they know you better, they won’t have much idea of what will do so. As a result, some of them may simply try everything in the book and see what works (if anything). Most of us guys are just wandering around in this minefield without any kind of map and just hoping nothing blows us to kingdom come.

  9. FitDarcie says:

    I agree, it DOES matter if he pays or not…at least on the first date. It’s one of the strikes, I give guys 3 strikes, so while not paying wont give him the boot, if he’s lacking in other areas, it could be the deal breaker.

  10. derek7272 says:

    FitDarcie, I feel the same way about girls offering to pay on the first date. I’ll always refuse her initial offer (well, at least if I have any interest in seeing her again). Some girls will then insist on paying half, which is always appreciated and impressive, although certainly not expected. But it does show some fairmindedness, IMHO.

    Some girls say that the person who invites should pay when it comes to first dates. But I feel like that is a little lame to say unless they actually ask guys out on first dates. Otherwise, they should be honest and say they want the guy to pay and not come up with odd way to sound gender-neutral.

  11. SINgleGIRL says:

    -jk228855
    Like I said when I started the post, I made no claims to be speaking for anyone other than myself. I think it’s really interesting how there are so many different ways of looking at this.
    -cjw666
    Interesting point. Maybe it’s the effort they’re making and the way it feels false to me that I find irritating. Who knows? It really is amazing to me that there are any couple on this earth.
    -FitDarcie
    And yet another opinion. I think it’s just amazing how all of the women here have slightly different views on this. Thanks for adding yours.
    -derek7272
    That’s valid. I think there’s a lot of confusion around the who should ask and who does ask issue that contributes to the issues around who pays. Jeez.

  12. Princess_electra says:

    Hear, hear!

  13. Tom says:

    I think this should be simple, but it does create a lot of tension on a date. The guy should always offer to pay, and so should the woman! A women turning her head when the bill comes is a turn off. A real man will be happy to pay but wants at least an offer of help.
    Tom recently posted..The Online Dating Guide for WomenMy Profile

  14. markdice says:

    It should be clear that there really is no “free lunches” with women. Offcourse it depends a lot where you live. Because in western countries it´s getting more and more casual that women pays at least half of the bill. But in any case they usually take it back in other things :)
    markdice recently posted..What You Need To Know About Dating After DivorceMy Profile