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Simply Solo Spotlight: There’s No Such Thing As A Free Lunch

March 22, 2011

Today’s Simply Solo Spotlight is by Simone Grant who writes the dating blog Sex, Lies & Dating in the City. Simone’s blog was one of the very first I read when I got into the whole dating/relationship blog world, and she’s amazing! I love her independence, and how honest she is about her experiences with love and life. Simone invited me to guest blog last September with Sex After The Ex, and I’m excited to have her guest blog on Simply Solo. I hope you enjoy this post!

Quick shameless plug: Do you have a story to tell? Advice to offer? Did you just have literally the worst date of your life and you must write about it? I’d love to have you as the next Simply Solo Spotlight! Contact me at:

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 economy is such a mess 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 think it’s a good issue to address head on. 

check, bill

You just had a great date. The bill comes. Who pays? And, who gets to eat this chocolate? Photo courtesy of Shutter Ferret

It kinda 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. If it’s different for people in their early 20s or daters in small towns, or in different cities? How the hell should I know? I’m no expert.

I can tell you what I know about me, and how money has and can affect my dating 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 New York City, 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. 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 knew that his apartment had to cost at least 4 times what mine did (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. 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.

21 Comments leave one →
  1. March 22, 2011 9:27 am

    Dating is one of the few areas where progress is somewhat stunted. I hear about girls who wait for guys to ask them out or call them back, or women who will wait years for a guy to propose. Call me new-fashioned, but let’s break the rules a bit here!

    And, I respect your POV. Nothing says romance like going dutch, right? I think your approach is great. I also appreciate your acknowledgment of the jerk who made you rethink that approach.

    Plus, I love this: “Let’s face it, dating is complicated enough without worrying about who pays.”

    Thanks for sharing.

    • March 22, 2011 12:27 pm

      Thanks. I just think it’s important to acknowledge that times HAVE changed and that nothing is as black/white as it used to be (or as we’d like to pretend it used to be).

  2. March 22, 2011 10:36 am

    I couldn’t agree more. I always go on a date prepared to pay, and when I offer to pay, I’m sincere. I don’t like a guy thinking he always has to pay – or, like you said, tipping the scale in his favor (lest anyone think I owe them anything). I dislike going dutch just because it makes the whole thing feel like a business transaction.

    • March 22, 2011 12:28 pm

      Thanks, Sue.
      Glad to hear I’m not the only one who dislikes going dutch. I’d rather pay the whole check than split it.

  3. March 22, 2011 11:09 am

    It’s perfect timing that you posted this when you did! And I agree 100%. But I have one question, who pays on your anniversary/Valentine’s Day?

    I have this friend who has been dating his gf for 6 years. For the last 6 years they have split the bill EVERY time, for everything, including Valentine’s day and their anniversary (which was just this past weekend). We’ve tried to tell him that when it comes to anniversaries and Valentine’s Day it would be nice if he picked up the tab for her every once in a while. He makes way more than she does, but he insists she is ok with paying half and always has. I’m assuming she is ok with it because it’s never been any different. What are your thoughts?

    • March 22, 2011 12:29 pm

      Honestly, I wouldn’t be OK with that AT ALL. Like I said, I hate going dutch. And if I dated someone who didn’t pick up the bill for Valentine’s Day – as a gesture, well, I don’t think we’d be dating much longer.

  4. 2blu2btru permalink
    March 22, 2011 11:24 am

    For me it depends on whether it’s a relationship or not. I pick up checks, cook at my house, and use my company meal card to feed my boyfriend and take some of the financial stress off of him, even though he makes nearly twice as much as I do, but that’s because we are in a relationship. I can’t really afford all of the eating out, but I would have to eat even if we weren’t dating, so cooking at home is my cheaper, easier solution. It helps that I can cook, LOL. Mr. Perfect and I have been dating for over three years, though.

    I don’t do a lot of dating–it’s never been my thing. I try to start all relationships as friendships, so there has been splitting of the check to start out with most people and me, or someone buying me a drink while I’m out. The first few dates, I would prefer him to pay, mostly because if I wasn’t out at his request, I’d be eating in, and mostly because I’m not a feminist and embrace my old fashioned, Southern Ways 😉

    P.S. I almost always have to choose where we go, as Mr. P seems allergic to it. But I always ask him for a clue as to price range and what he wants to eat (“What do you feel like having?” “Are we just getting something quick or more substantial?” etc.).

    • March 22, 2011 12:31 pm

      Like you, I continue to take turns paying even when I’m in a serious relationship. Even when the person I’m in a relationship with makes a lot more money than me. It’s just what I feel comfortable with.

  5. March 22, 2011 11:45 am

    Love it!

    Very well written!

    Friends split checks, lovers and daters do not!
    I have no problem paying for myself should a date go that way, and I never assume he’ll pay.

    Although if it’s a first date and he doesn’t pay, that tells me he doesn’t think I’m worth it or is interested enough and I move on. Second, third dates etc I’ll pay or cook for them etc.
    It all depends where in the relationship we are. If I’m into a guy, I prefer cooking at home, hanging out in the kitchen prepping together. There is something casual and intimate about hanging out in the kitchen.

    Love this post.

    • March 22, 2011 12:34 pm

      Thank you. And honestly, I think twice about a guy who doesn’t insist on picking up the first date tab. Which is why I sometimes show up to a bar early and order/pay before a guy gets there (to avoid the whole paying thing, if I think he’s broke).

  6. March 22, 2011 12:47 pm

    I agree. It is a case by case situation. What I find interesting though is that many of the books and blogs I read by men on this subject usually say that the man should pay for every date (or at least most of them) even if they make less money than their female date. I’m not sure what to make of that. But I do hold true to my rule of the guy paying for the first date. I am like you and try to make sure I’m a cheap first date but he does need to pull his wallet out. That’s just one ‘my tests’. Great post! -SG

    • March 22, 2011 5:10 pm

      Thanks so much. Honestly, I don’t read much dating advice (unless it’s written by friends or writers I know and respect). One post I read (by a male writer I know) said that a guy should always pay for the first 3 dates and that seemed like decent advice, from one guy to another. BUT I still wouldn’t feel comfortable letting someone with much less $$ than me spend his $ on me. That’s just me, though.

  7. March 22, 2011 2:06 pm

    Since you brought it up, I live in the midwest. I do think this has bearing on this topic to a certain point. (Or maybe I have just dated a bunch of lame-o guys.) But in my experience it seems that once I pay for something the guy stops trying to care for me or impress me with thoughtful or fancy dates.

    It’s like as soon as I show a guy that I can take care of myself (which obviously I can or I wouldn’t have lived to the ripe old age of 31), and maybe take care of them from time to time, they stop caring for or doing anything to take care of me. Or they put me in the mom category and expect me to take care of them all the time.

    Sometimes I think I must be searching for some sort of rare, unicorn of a man. But my personal hope really is that there is a guy out there who is my equal. A guy who can take care of himself and take care of me sometimes too. A guy who won’t be threatened or become lazy because I’m a capable woman.


  8. March 22, 2011 5:13 pm

    I’ve always suspect that age/location and other demographic issues affect this. I live in NYC and the guys I date are probably (much) older than the guys you date. I don’t think I’ve ever been put in the ‘mom’ category.

  9. Claudia permalink
    March 23, 2011 12:38 am

    Agree with this entire post. Especially: Friends split checks. Not lovers

    First date (unless I ask) – he should pay. It may be antiquated but it shows level of interest. If I’m not interested in him by the time the check comes, I’ll offer to go dutch. Then again I won’t accept a drink from a guy whom I have no interest in.

    I’m all for equality. However women still make less on average and have fewer advancement potential. Until that changes and if the specific guy makes more, he certainly should pay more often than not.

    My recent ex made a considerable amount more money than I did. He paid most of the time. I cooked for him often though including a week of leftovers for lunch. If at my apartment, I’d buy the groceries and paid for the takeout meals. At his, he would. I also took him out on a few occasions. As with you, I preferred the method of: who asked and picked the location pays.

    However the last time we went out, he picked the place (rather pricey) and asked to go dutch only when the check came. I honestly was barely scraping by that month as it was and he knew it. An emergency trip back home for a funeral 2 days later and moving at the end of the month. Livid doesn’t begin to describe it.

    You are correct that it tips the balance of a relationship. Even though I was upset, I didn’t say anything. Just quietly paid my share. I wouldn’t have broken up with him just for that, but it certainly added to the scales when he fucked up a week later.

    • March 24, 2011 11:48 am

      I don’t think it’s antiquated to think a guy picking up the tab for a first date is a sign of interested. I think it’s a pretty common belief.

  10. March 23, 2011 12:23 pm

    Well, call me old fashioned, call me a male-chauvenist (even though I am very much a woman), I believe that a man pays… a man always pays… a woman never pays unless she loves having low self esteem. If a man is courting a woman, then he should show her that he can take care of her. There is no equality in the work force, no equal opportunities or equal wages. Women’s lib failed us and made our lives harder and more complicated and confused male/female relationships.

    Courtship and pursuit and romance are sexy and a huge part of a relationship. A man should show respect for a woman and pay. After all what he is seeking first and foremost is getting his d*ck ____ do I really need to finish that sentence? Men want regular sex. Women want just a little pressure relief in their lives, and someone they can rely on.

    The ONLY times a woman should pick up the check is if she is in a stable relationship with a man (ie: married or engaged to be married) and the significant other doesn’t have his wallet on him, or if she is out with a male friend and she wants to make it VERY CLEAR that under no circumstances whatsoever is he getting laid.

    Forget how much he earns and whether he can afford it or not. Have a little self-respect ladies, and figure out your worth. Are you not worth a $5 latte, a $30 lunch or a $80 dinner? REALLY!?!

    If you want to give your attention, your precious body, your self-respect AND your hard earned money to a man, and feel raped and taken advantage of when he doesn’t call the day after you have sex with him…. or never calls, because he got what he wanted, go ahead and keep paying for half. You’ll also end up paying for a lot of therapy.

    For more on this subject, see my blog Silent Night, Horny Night – why women should ban the one night stand

    • March 24, 2011 11:50 am

      I’m sure there are plenty of people – both women and men – who agree with you, but I’m not one of them. I don’t see how a man paying for a date have anything to do with my worth as a person or a woman. That’s beyond old-fashioned. More like belittling.

  11. March 23, 2011 2:09 pm

    It’s a pretty sad commentary on our social life-styles when $$$ plays such an “important” roll.

    I’m an old fashioned guy. Regardless of who asked who I am definitely paying for the first date. Then, I’ll likely pay for the few preceeding ones as well, but it’s appreciated if a woman puts up a fight for the check in a little ‘Tab Tug-o-War’.

    If I really like someone…I don’t really put a price on how much I’ll spend. Trust me, I don’t have a lot of money to throw around; but if I’m going to take someone out I don’t want to have my budget looming over my head.

    Just don’t be disappointed later on in the relationship when some of our dates are cheap chinese carry-out, $5 bottle of vino and a Redbox rental. 😉

    • March 24, 2011 12:01 pm

      When you look at what married couples fight about the most (based on surveys) money tops the list. And a recent informal survey of singles had most of us stressing about $. So, it makes sense that $ is a big deal in dating. It IS a big deal. I’d rather deal with it head on than pretend it’s not important.

  12. April 2, 2011 9:51 pm

    I absolutely agree that $$ must dealt with during dating phase in a pleasant and open manner.

    For celebrating a lover’s birthday, anniversary of knowing one another, etc., no it should be a real gift from the partner.

    But anything, in term of food, split in down in half. Both individuals need to eat. There’s really nothing to analyze about that. You just have to find something that fits the budget, especially one person may be earning alot less. Then the wealthier partner has to scale down food budget or they pay for the balance if insisting on expensive meals, etc. Can’t be that hard. Really this is one area, we never disagreed.

    For foods other person doesn’t eat at all, then just pay it yourself.

    I don’t know what to say…this seems incredibly trivial. I just signed to buy a home recently.

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