If He Doesn’t Pay Should She Still Play?



Author : KC 
I went on a date last night with a guy I met online.  He suggested dinner and I thought it was a very gentlemanly thing to do.  The date went fairly well – conversation flowed, he was extremely complimentary, telling me I was far more stunning than my posted pictures and he was shocked at how well we seemed to click. We discussed family, jobs (both have great, well-paying jobs) and aspirations.

Near the end of the meal, he asked when he could see me next –  again telling me he was thrilled with his first impression and excited to see where this may lead.

I was flattered and also a bit excited.

BUT…when the bill came, he sort of reluctantly took it and then asked me for HALF…  I must have turned white – I was so shocked.  I of course handed him the cash and then a quick hug and bee-lined for the door.

I made the mistake of giving this bozo my phone number and now’s he’s a texting maniac – asking when we can see each other again.  I don’t want to sound superficial but I am so turned off by this tacky behavior (dinner was at his suggestion and I am a very generous person and would happily pick up future tabs).  How do I tell him to take a hike and hopefully teach him a little something about how you treat a lady?

Advice would be most welcomed – Thanks!!!


He reluctantly took the bill because, possibly like you, he was having a really great time and he was looking to see if you would offer to contribute to the bill. See, that who pays test works both ways. Unlike you, he’s willing to brush it off and give it another go.

Here’s what your real question is: How do I swallow my pride and accept a date with this guy again without looking desperate or losing my power? If you truly had no interest in seeing him again, his texts wouldn’t bother you. You’d simply reply back and tell him something suddenly came up and you won’t be seeing each other again. People who complain about all the pestering texts they get from folks aren’t really griping. They’re bragging. You, love, are bragging.  So accept the date and move past this, because you know that’s what you want to do. How much more does he need to do to woo you? He agreed to dinner on a first date, something no guy does. The conversation went well. He showered you with compliments. You got the majority of The Girlfriend Experience. Which, frankly, I see as a red flag. Not sure how genuine this guy is. For that reason alone I’d want another date.Experienced guys know that dinner on a first date is a no no. So he’s either inexperienced or disingenuous. Only time will tell.

Was it as simple as he “reluctantly” took the bill or did he sit there and watch you steadfastly refuse to even pretend to want to pay your share. If I were confronted with that sense of expectation and entitlement, I would probably do exactly what he did.Who the hell is anybody to expect me to spend my money, money I work hard for, on them just because they agreed to meet me for a meal?

First dates aren’t all about the man working to impress the woman. It’s about both people trying to make a good first impression. You don’t seem at all concerned that maybe you failed the test. Because you did. While many women will turn to friends or the internet to complain/brag about their date with the cheap Unicorn, most men will just chalk it up to poor communication. They might even make a judgment call that the woman is possible spoiled or entitled. They don’t crowd source the experience. They decide to either file that away and give it another go or to blow her off and move on to the next.

Maybe by asking you to help pay, he was trying to teach you a lesson about how to treat a guy.



Sometimes the love of your life is the love of your life. (R)


One on One Dating Profile Review

Get a 45 minute one on one review of your profile with me.  I’ll go over your picture selection and ad text and let you know if your profile includes any buzz words or red flags. I’ll also help you tweak/write your profile if it needs some freshening up.


  • *Profile analysis (45 minute phone session.)
  • *Assistance with editing and re-writes.
  • *Photo selection and review.
  • *Feedback about specific issues and experiences.
  • *Site selections  and Pros & Cons of the more popular dating sites.
  • *Overview of online dating basics – how to write intro messages, how to draw more attention to your profile, how to sort your searches so you can see profiles you might be missing.

$55 (Use code BLOG to save $10)


Eventbrite - Master Match.com & OKCupid

Related Posts Plugin for WordPress, Blogger...
, , , , , ,

44 Responses to “If He Doesn’t Pay Should She Still Play?”

  1. bbdawg Says:

    If a man asked me to split the check on the first date I’d consider keeping in touch with him – as a friend. Splitting the check on the first date is the ultimate friendzoning gesture. I have offered to split the check spontaneously only when I knew 100% right there I never wanted to see the guy again.

    One guy I dated a couple of years ago asked me to split the check on the first date and I said no. We dated casually for a bit and he did say he was not looking for a serious relationship in the long run. Splitting the check in my experience comes from a man wanting to be casual, since paying is a courting gesture.

    This goes back to, if paying for dates meant that men were “impressed” and that it somehow translated into commitment, women would do it in a heartbeat. We all know, however, that unlike us women, many aren’t persuaded by career success or being “wooed” by a woman through cool dates. That doesn’t really work to get a boyfriend. Sure you can get dudes who don’t care/”aren’t looking for anything serious” but that isn’t the point of dating for most women.

    • Dave Says:

      I wonder if there is a correlation between women who expect the man to always pay vs those who are also very active on dating blogs when they are not actively dating.

    • GI_JANE_is_back_yall Says:


      Pay your portion and NEVER SEE HIM AGAIN.

  2. Kathy Says:

    I would feel upset also if the man suggested another date but didn’t pay for the first one. It feels like an insult actually. She really doesn’t want to go out with him again, but she wants to figure a way to tell him that. It was the request to split the check that caused her to feel that way.

    • Cooldude Says:

      Sounds to me like all was well until he asked her to split the bill so this seems more like someone clinging to an old fashioned law.

      • bbdawg Says:

        I can see where this is coming from. Re-reading her letter it could also be that the guy who “makes a great salary” – just like hers – could have been tired of paying for dates and decided that since he is in demand, he won’t pay going forward. Period.

        I still find the lack of “investment” bothersome, maybe I am old-fashioned indeed. To me it means this guy isn’t serious, esp. if he was as complimentary as he was in person.

        Maybe, if the OP really doesn’t care about this guy she should politely tell him what she is telling us and see how he responds. That’s the only way to find out. Maybe he has a legitimate reason (i.e. he is tired of paying for women who won’t sleep with him in the end), or maybe he is just a player who loves paying compliments but prefer splitting the bill.

        Like “hey thanks for all your texts…I genuinely liked meeting you but I was a bit surprised when you asked me to split the bill with you … I was under the assumption that especially a man likes you and asks you out – and you clearly were very complimentary during our date – then he pays for dinner. Since you came up with the idea I didn’t give it a second thought until the bill came. I might be old-fashioned…I was confused because when a man doesn’t pay to me that is a friendzone sign. Maybe I overreacted:).

        If he likes the OP still after that he might have a legitimate reason. To me the extreme complimenting about her looks and being “shocked” at their connection is more of a red flag than the not paying. It says “player”/time waster to me more than anything. It doesn’t come off as genuine.

  3. SS Says:

    In the land of online dating I think to expect men to pay 100% for the “first date” is completely unfair.

    I refuse to commit to anything more than drinks, but I also don’t consider it a date. A date is when 2 people are attracted to each other and want to see where it goes. When 2 people meet after connecting online, who the hell knows who the other person IS really, let alone whether there’s attraction. Why should a guy have to pay for a total stranger??!!!

    So generally I (try to) insist on paying my way on first meeting, and if he wants to see me again and/or pay at the second meeting, then great.

    • Laure Says:

      I totally agree. How can you expect someone you have never met to buy you diner? Even if the guy suggested to go out for a bite, this doesn’t mean he has to buy your food.

      So sad that this guy is being called a “bozo” for a stupid, old fashioned dating rule. Must be an American thing. :-)

      • SS Says:

        Definitely find the ongoing debate to be an American thing.

        In England only the spoilt “expected” to be paid for. In my experience automatically going Dutch (splitting 50:50) was the most common scenario.

  4. Jess Says:

    “He agreed to dinner on a first date, which no guy does.”

    I’m not sure if it’s my age (26) or location (very small town, definitely not NYC) but 98% of my first dates have been for dinner…that the guy suggested. Depending on how well the date was going/where we were, occasionally dinner would turn into drinks afterward. I always assumed this was normal. Is it not? I’m genuinely curious here.

    • SS Says:

      I’d say both are definitely factors – in the early/mid 20s vs 40s and older:

      – you’re less “fully formed” personality wise and more likely to match, therefore the expense of a dinner is more likely to pay off for prospects

      – 20s are less jaded, more optimistic about potential

      – 20s often live at home or with roommates = more disposable income

      – older men generally have commitments, eg mortgage, kids, ex… therefore less disposable income

      And small town = less prospects. It’s easy to pay for dinner for 5 potentials than if you were in NYC and there were 500 potentials.

    • Lisa Says:

      I agree w/ you. I’m 42 and ime, most men have have suggested dinner and paid for both of our meals. Some suggested lunch, coffee, ice cream, movies, but def more than half of my first dates have been dinner (suggested by them) and the guys paid.

      The guy in the story is tacky. Period. Whoever asks should pay (under most circumstances). I have no problem paying for dates, let me be clear! But not a first date when I was the one invited out.

      I don’t think the LW needs to delete this guy’s number. I don’t think his behavior is a dealbreaker. But if I wanted to go out w/ him again, I’d wait until he asked and then confirm that he is, in fact, taking me out on a date.

      • Isambard Says:

        I like, as Lisa said, that whoever asks pays. If I ask someone out for dinner, friend or date, I’m paying. Group things or hanging out are, of course, different.

        What raises a flag with me is, one: if the person doesn’t say thank you (that’s just bad manners no matter who it is), or two: someone who doesn’t reciprocate, by asking me out for dinner or something similar that is their treat.

        It doesn’t need to be a 50/50 score card, but I like to see some courtesy, appreciation and generosity.

        PS: Why do ladies go out with men who expect sex for buying them dinner? Seems to me you can generally tell if a man is like that in the first few minutes of conversation.

    • Donnie K Says:

      If you met these guys in real life then I would say that your experience is normal. Online dating is totally different. You don’t even know if you’re attracted to the person until you actually see them.

      • Jess Says:

        With the exception of one, I met all of them online. I never seem to meet guys “out in the wild” as I like to put it, which is largely due to my hectic work schedule, so I tend to gravitate towards the online dating platform.

  5. E-B Says:

    There will never be a consensus on this topic, but here is my take. I am a guy, so I expect to pay for the dates. But I do like to see some acknowledgment that I’m doing that. Either the reach for the purse, or “thank you so much for dinner,” or some recognition that I’m doing something nice. If they don’t do that, forget it- they are toast. It’s like the door test from “Bronx Tale”:

    One other thought- I hate it when women refuse to pay anything on first dates, and then claim “I am a very generous person and would happily pick up future tabs.” Really? You mean to tell me if the guy offers to split every other check, the women would be okay with that? OF COURSE NOT!!!! I’ve learned that when people adamantly claim something, it is usually not true.

    • uesider Says:

      “I am a very generous person and would happily pick up future tabs”- but sorry dude, 90% of the time its a one and done date. I happen to think regardless of future dates, women should at least offer sincerely. In particular when they damn well know that they aren’t going out with the guy again.

      On the other hand, fellow guys, don’t bring up spliting the check on the first date, unless she was awful company and you honestly don’t care whether you offend her or not. And don’t sit there calculating the bill to the penny, whatever you do. Bring cash, round the bill so you don’t have to wait for change, and go.

    • Shadowcat Says:

      Enough with the door test, already, when we were kids, out was mandatory for everyone to do it. When we got older, w knew it would be noticed by guys ( Bronx Tale didnt invent this, it wa a tthing) You could be the biggest bitch in the world, but you still did the door thing because you know it would be noticed. My boyfriend complained thst I didnt do it 15 years ago and I told him that I just forgot about it, it had been years since I had been in a car that didnt have remote locks… Stupid test…

    • Katie Says:

      I’m not sure how to take the issue. On the one hand, the first and second dates I’ve been on (whether coffee or dinner) the guy has always paid. That being said, I always offer when the bill comes to split it (and they usually say no and something along the lines of “I chose the place, I will pay, etc”). But if I offered to split and they agreed, I’m not sure I would be offended. I’d probably agree to pay, since it’s only the first or second date – we’re not really committeed to each other.

      I guess my only advice is never do dinner for the first date. I learned that rule a long time ago, and I always do coffee dates for my first one. If i have to pay, it’s only $3 or less for a cup of coffee. If they guy pays for both, once again it’s only $3. If things work out with the other person, then it’s time to make serious plans and go for dinner or brunch or something else.

  6. Dave Says:

    This all sounds so incredibly complicated. I just like to meet people and have a good time. Over ANALysis, yes?

  7. BTownGirl Says:

    I have to wonder how many women there are out there who, like me, got 1950’s-era dating advice from their mothers and thus spent their Formative Dating Years hearing, “The man pays!! If he asks you to pay, he doesn’t like or respect you! Bad sign!” and, unlike me, didn’t have friends who got more progressive advice at home and thus could tell them that’s malarkey. In general, I think first dates are “whoever asks, pays”, BUT in this case the date was a full dinner and it sounds like both KC and her date are established professionals, so…who cares? I’m not sure about the date’s intentions either, but the only way to find out is to go on a second date. Have some fun, for chrissakes!

  8. Nicki Says:

    I wonder if the OP actually reached for her purse or not when the check came or if she totally assumed her date would pick up the tab?

    I have always gone on first dates being mentally and financially prepared to pay for my half. I have always reached for my wallet and always offer to pay my half. If the man insists on paying then I thank him immediately I would attempt to push a little harder to pay my half if I knew that I wasn’t feeling it.

    • SS Says:

      “I would attempt to push a little harder to pay my half if I knew that I wasn’t feeling it.”

      In that situation I tell them “in England the woman always pays her way on a first date” – that way they buy it and I don’t feel guilty! :)

  9. Cooldude Says:

    Do we need another “who pays for the first date” debate? Never going to be a consensus. I will say, I DO find it interesting how women’s rights continue to (rightfully so) be a big issue in the media. However, I still consistently read and hear from women who are SHOCKED that someon would expect them to pay for food/drinks they CONSUMED with someone they barely know.

    • SS Says:

      “SHOCKED that someon would expect them to pay for food/drinks they CONSUMED with someone they barely know.”

      And yet, in my experience, I consistently read and hear from men who are outraged that women won’t automatically put out with someone they barely know.

  10. Confused Says:

    There’s one thing I don’t get. I’m genuinely confused, not trolling. There seems to be a recurring theme in this blog about not taking women to dinner on the first date. Is that really the standard in modern dating or is it just an east coast/NYC thing? In my experience in the Midwest and west coast, men routinely asked women out on dinner dates and never thought twice about it.

    • K Says:

      I’ve dated in NYC as well as several west coast cities. In my experience the norm is to suggest drinks. If that’s going well I’d say 9 out of 10 times the guy already has another nearby dinner spot lined up (as in hey want to get a bite after this) or lets order some food. When we or one of us isn’t feeling it it’s much easier to end at drinks especially with the variability of meeting people online. I’d say it’s more rare to do dinner from an online date, although some have offered, and if there was a lot in common early on (mutual friends, same schools etc) I have agreed as I know we would have stuff to talk about.

      • Confused Says:

        Hm, good point. I guess the difference is from online vs in person. When you already know someone well from mutual friends or work it’s easier to say “wanna get a bite”.

  11. Zaire Says:

    LOL I wonder if some of the people writing in even read this blog. Or do they just search “online dating blog” looking for a place to vent. OP couldn’t have seriously thought you would cosign her entitlement given your previous responses to similar letters.

  12. natalie Says:

    I date a lot and have had a significant amount of guys ask me out for dinner dates. This is not strange or unusual in my opinion. Also, maybe I’m old fashioned but I do expect the guy to offer to pay for the first date, regardless of what it is, coffee, drinks, dinner, anything. I like a man who has manners. I do always offer to chip in but if a man accepts it I do wonder if he’s cheap. On subsequent dates I wouldn’t mind splitting or trading off on who pays if we end up dating or in a relationship.

  13. The Original D Says:

    Another woman who wants all the benefits of feminism and none of the responsibilities.

  14. Shadowcat Says:

    I can’t believe how often this subject has come up here. If I ever end up in the dating pool again, I will insist on coffee/happy hour first dates only, and I’ll pay my own way. After, if I’m interested, I’ll send him a text letting him know how much I enjoyed the date, and I would love to see him again. (So he doesn’t assume that I paid because I wasn’t interested.) It’s not worth all these mental gymnastics. I think dinner is a pretty big time commitment for an online date anyway, if you met IRL, you at least already know you are attracted to each other, and connect on some level. Online meeting is a crap shoot.

  15. coffeestop Says:

    I have no problems splitting the check. In fact when I don’t know somebody well, I almost prefer it so as to erase any assumptions of something being owed. I have been in such a rush to get out of a date that I paid myself just to avoid lingering.

  16. Mark Says:


    This topic will almost always be a matter of contention and debate.

    I believe that to a large extent, there are two Key factors that cause this to an issue: communication and expectations.

    As applied here, both of you might have done a little better.

    Here is why:

    You mention that this was a first date. Date as in first time you two actually met. He suggested dinner. You agreed. By and large the person who asks the other out picks up the tab. At least in the initial stages. However, if the amount is more than a small amount, it is also generally a good idea to share the expense. Or at least be prepared to do so.

    Here is where communication and expectations come into play. He might have made it known to you about splitting the check in some way. He failed to do that and assumed that you would be ok with picking up part of the tab. You knew the meet was for more than a drink to get acquainted. You might have inquired about something less substantial or broached the subject yourself if you felt uncomfortable.

    These assumptions by both of you and the lack of clear communication that led to the awkward position that both of you experienced. You both assumed incorrectly. Perhaps understandably, but erroneous non the less.

    Again, I can totally see both sides of the argument. Your as well as his. Factor in the idea that different parts of the country (or world for that matter) may have different generally accepted customs. Toss in different demographics as well as the specific individuals and I think you can see that this is why managing expectations and clearer communication can improve things.

    If you and this guy had done this, you both would have had a clearer idea of who each other was and where they are coming from. At least from the onset. If his position was something that you simply didn’t care for, then you simply could have concluded “Thanks, but no thanks.” Ditto for him.

    Best of luck and hope things improve in the future.

    • Lisa Says:

      Mark said,”You knew the meet was for more than a drink to get acquainted. You might have inquired about something less substantial or broached the subject yourself if you felt uncomfortable.

      These assumptions by both of you and the lack of clear communication that led to the awkward position that both of you experienced. You both assumed incorrectly.”

      You think it’s fair to say she assumed something incorrectly?

      How should she have broached this? I’m totally serious. She should have asked him on the phone, before they met, if he was planning on paying? Or, after he suggested meeting at O’Charley’s, she should have countered that with, “no, let’s meet at Starbucks. I insist upon Starbucks”?

      I can see if the person asking is grasping for ideas of where to meet, for the other person to steer him/her in an economical direction, and suggest coffee. But to me, it would be just as rude (as asking a date to split the check) to haggle over the price point of various restaurants, etc., when someone has freely chosen to invite you to a specific place.

  17. Lucy Says:

    I don’t have a firm view on this. I have no objection to splitting the bill and I certainly don’t expect for men to pay for me every time. I try and make this clear to them on a date. However I appreciate when a man pays for me because it’s what he wants to do and he wants to impress me. If a guy is putting more effort into a date and showing his generosity by paying for me I assume he is more interested in me. That definitely gets me more into him. It’s not because I think he should. I just see it as a kind gesture. I’m going to come across as unpopular on her and say that if a man invites me for a coffee and doesn’t offer to pay for one drink, I think he sees me as a friend or is hedging his bets. If I have been dating a man for more than a few dates, I put forth more effort and re-balance things.

    • The D-man Says:

      However I appreciate when a man pays for me because it’s what he wants to do and he wants to impress me.

      The second part is true but the first usually not. Most guys pay because it’s expected, not because they want to do it.

      • Lucy Says:

        Yeah I agree that that’s generally true. Some guys genuinely want to do that though. Bottom line is that if I like the guy, I’m hardly going to reject him over the “who’s going to pay?” argument. It seems awful silly. It should be a give and take thing.

  18. Dori Says:

    The only advice I can give is that next time a guy suggest dinner as the first date, say that you’d rather get together for drinks and apps. Dinner on the first date is a bad idea.

    I am confused though. If you want him to take a hike what is the point of teaching him how to treat ladies. Just block his number or tell him that you did not feel chemistry or that you are getting together with an ex.

    It is possible however to teach the man you are dating to pick up the checks. Rori Rae has a great advice on how to do it. But that is for a guy who you want to have a relationship with, not for a guy you want to take a hike.

© 2013-2018 And That's Why You're Single All Rights Reserved