The Real Reason Men Won’t Let Women Pay For Dates

Alias (DO NOT USE A REAL NAME!!): Lizzzzzzzzz

Comment: I’ve been dating this really great guy for about 2 months, and we’ve been on about 7 or 8 dates total with plans for many more in the future.  Our dates go great.  The only thing is, he pays for all of our dates.  I know, I know –  I’m going to get made fun of for bringing this up and complaining, but at this point should I still let him?  Don’t get me wrong, every time the check shows up at dinner or drinks or brunch I offer to pay or split it, but he always tells me it’s fine and pays.  And so far we’ve split any expensive activities (he pays for himself and I pay for myself, like the one date we went to a museum).

I guess my question is, is he sick of paying? Is there a point in a relationship when a guy gets sick of paying for everything?  If a guy didn’t want to, would he let me pay for half, or just suck it up bitterly?  Should I keep offering, or am I just going to get to the point where I offend him for asking every time?  Cause I’m happy to stop asking and let him pay, I just don’t want to come off as a freeloader, because I really like spending time with him.
Age: 29
City: NYC
State: NY


Here’s what makes this scenario so tricky: many if not most men believe that a woman offering to pay for anything at this stage of the game is a test. Accept that offer, and he’s labeled cheap or just in it for sex or not a gentleman or whatever.  That’s why most men continue to fork over money for dates. They know that allowing a woman to pay her share will be held against them.

You should not be offering to split it. You should be picking up that leather bill fold and sticking your credit card or cash inside of it, no conversation necessary. This is why I always side-eye women who leap to assure everybody that they try to pay their way.  Like, duh…of course he’s not going to accept the gesture. That’s why you don’t sit there waiting for that awkward pause to play out until he grabs the bill. You grab it.

Is there a point in a relationship when a guy gets sick of paying for everything?

Yes. It’s called The First Date. Nobody wants to spend their money on another person all the time. Nobody. Even people who really, really, ridiculously like you aren’t thrilled at the concept of paying your share of a meal or movie ticket. It’s the principle of the matter. I can assure you that guy has things he’d rather spend his money on than you. Which isn’t to say he doesn’t like you or that he resents you. I’m sure he does care for you, which is why he keeps paying. The myth that men “like” spending their money on women was started by some try hard man or woman who wanted to impress people. It’s not real.

Cause I’m happy to stop asking and let him pay,

You don’t say.

You need to stop asking and just do it. Trust me, very few men believe a woman when she says she wants to pay for something. The bottom line is that if you truly wanted to pay, you’d find a way to do it. And he knows that.


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 & OKCupid

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

44 Responses to “The Real Reason Men Won’t Let Women Pay For Dates”

  1. DrivingMeNutes Says:

    Most guys are wary of being taken advantage of by women the same way women are generally wary of men. This is especially true of men with resources who, not coincidentally, are frequently the ones who are “generous” because duh they can afford to be. Before I’d get all giddy about a guy paying -and taking it as some awesome reflection on how we feels about you, – I’d ask myself how much of a sacrifice paying is really to him. Personally I’d be more impressed with a guy who didn’t have a lot who was generous with what little he had but I know that’s not this world.

    There’s really no way around this. Either he’s waiting for you to pay once in a while (not “offer”) to show that you are not the type to take advabtage or he has odd views on women and their subservient roles in relationships. Only the latter would be actually offended by a woman paying. The rest are just pretending to be.

  2. Z Says:

    My thoughts? You make some good points but they so often get buried in your latent bitterness and hostility. Oh. Right. That’s just “real talk”…

    That aside, from this guy’s perspective:
    1. It’s a test on the first date, sure, and I suck it up and pay. I do resent the expectation that we should have to by ritual pay for even the first date. What makes a woman’s time so much more valuable than mine that I should be paying for the privilege of it?

    2. But barring some particular reason to do differently, I’m accepting her offer to pay on date 2 every time and would be bothered if she only offered to split that. Now *she* seems cheap.

    3. I differ that 8 dates out its still a test. That guy is a sap and weak sauce for feeling so insecure that he has to keep covering the bill. His behavior says more about him than her. Saying “yes, thanks” to her offer would be easy.

    4. Sure, or could just grab the bill, slap down a card, smile and say “my treat tonight.” I’m sure most men would appreciate it.

    • DrivingMeNutes Says:

      “That guy is a sap and weak sauce for feeling so insecure that he has to keep covering the bill.”

      Yeah I’m sure he’s coming home from a hard day working at the docks and blowing his whole day’s pay on this unappreciative woman. More likely, he has loads of money, most of which gifted or inherited from his parents, or derivative of them, and it is no skin off his back to always pay and he knows women will be impressed. These guys are a dime a dozen in a NYC. They aren’t “saps” – they are offering what women want. We all do it -using what we have to get what we want. Don’t you?

      • Z Says:

        Your post reminds me why I hate New York and live in Boston.

        Leaving aside your assumptions about how someone night have gotten their money, you just come across as angry. “…they are offering what women want”? Some women want a sugar daddy but to say that it’s such a large percentage that men have come to believe all women want to freeroll on some guys dime is absurd. Omg..and he’s so wealthy too!

        And no, we don’t all use what we have to get what we want. Or better sais, don’t use everything we have…or don’t apply the any means necessary approach. People looking for a real relationship especially may choose not to. Do I want her to love me or my money/fame? Does he like me only for my looks or does he find my intellect engaging and fascinating?

        • ATWYSingle Says:

          @Z – You seem to confuse matter of fact with angry and bitter. I can’t even tell what about this post you disagree with. Like DMN said, most guys continue to pay a) because they can and b) because it’s the path of least resistance to what they want. If you don’t know that a large majority of women expect a man to continue paying for a good portion of the courting phase or refuse to pay anything until commitment is offered, then you don’t date much, my friend.

          • Z Says:

            *start rant to get it out of the way*

            Your version of “matter of fact” generally comes off across your writing as somewhere between angry, bitter or a case of “I’m speaking my truth” and therefore it’s fact…to this 48 year old single male Bostonian. My comment on this is really based on everything I’ve read, not just this post, so it may be a larger reaction than warranted, but still on point. (Apologies for the cumulative nature of that).

            The most likely reason for the difference is that Manhattan is an island in more ways than geography. Your views are reasonably shaped by your NYC experience – which I think on occasion makes the reader need to take it all with a grain of salt if they aren’t in NYC and a small number of other places.
            *End rant- on to the actual opinions*

            I *agree* with 90% of what you wrote in the post and am in total agreement in principle.

            Where I differ is here:

            “Trust me, very few men believe a woman when she says she wants to pay for something…” and “many if not most men believe that a woman offering to pay for anything at this stage of the game is a test.”

            Wow. That’s either markedly cynical or the dating scene in NYC is even worse than you portray it. If that is the NYC reality then I truly feel sorry for both sexes sucked into that dating pool. Men are thinking 8 dates in they are still being tested?

            If a woman offers, I do stop and consider the offer for a second to decide whether it is the obligatory offer or a heartfelt intent and respond accordingly. On a first date I’m refusing regardless and just paying, heartfelt or not.

            But by the second or certainly the third, I’m accepting their offer. If it was sincere, great! That’s an expression of appreciation. If it wasn’t, and they are offended I took them up on it, it wouldn’t work out anyway.

            Also, you said “…most guys continue to pay a) because they can and b) because it’s the path of least resistance to what they want.” I can easily afford to pay, but it’s not about whether I can afford to. This should be a two-way street, especially if you are with someone of similar economic status. Someone offering genuinely to pay I see as a gesture of interest in the potential or the relationship.

            “If you don’t know that a large majority of women expect a man to continue paying for a good portion of the courting phase or refuse to pay anything until commitment is offered, then you don’t date much, my friend.”

            I do date. I don’t date in NYC. I don’t date women looking for a meal-ticket. I date women generally 40+, not vapid 25 year olds. I can’t ever remember somoene waiting 8 dates before forcibly paying the bill or making some other real offer at paying/splitting/alternating etc that I knew to be heartfelt. (Nor have my I ever heard a female friend express similar sentiments to yours)

            On what planet are women expecting a free economic ride until they get a commitment? I understand the argument for not having sex until commitment, sure. But “you’re going to lease my time until you are ready to buy?” yikes!

            Women earned the right to vote, drive and equal pay and opportunity (some of those have a way to go but the point is the same). Expecting 8 dates on his dime is hypocritical, unless you want to not be able to vote without having donated to the candidate first.

            A number of the posters here are also Bostonians or live outside major metros. Am I the only one thinking Moxie’s opinion here is very Manhattan-centric? The geography question may be more interesting than the OP.


            • Jonathan Says:

              Wow, I wouldn’t read a blog written by you, Z. Your writing oozes with anger and bitterness, that unlike Moxies, is not wielded to awaken any insight. Your quest for perfection is at the cost of progress. Shame, your style of expression likely makes it hard for those who even agree with you to be able to help you become a better version of yourself. hopefully when your not ranting, that you are open to feedback from intimate ones without having your filter of perfection cause you to reject their efforts. best wishes, Z.

            • Harold Says:

              People from Boston have no manners just like “z”

    • ed Says:

      This reply is split right up the middle. How much you want to bet it’s mostly men thumbs up and women thumbs down?

  3. Z Says:

    Hit enter too soon.

    The only guy still paying at 8 though, and who might be offended at her offer, is measuring his manhood with his money.

  4. coffeestop Says:

    I went out on a bad date this summer and I want to get out of there, my date was weird and hostile, so I asked for the check and paid. He actually called me up for a second date purely based on his intention to have paid for the first time. I was like Wut?If I have a date I always show up with cash to pay half or offer it to the person I am with if they want to put it on their credit card. I do not turn it into a contest but most of the time they decline. I have mixed feelings, on the one hand men seem to complain when they are “expected” to pay for the date, on the other hand I have had some weird reactions when it was obvious I intended on paying my share. So I don’t really know what the right answer is when I am getting to know somebody I always suggest a reasonable/moderate priced place if my input is asked. No way I would go to a pricey place until I knew them better and in my city there is a wide range of moderately priced places. I think this becomes more of a sticking piont in the LA/NYC types places where everything is expensive.

    • D. Says:

      The hostility/disappointment is because of the unspoken social contract that men are expected to pay in early dating. If a woman insists on paying, especially on a first date, it’s usually because she thought the date was bad or she wanted it to be clear that she wasn’t that interested — just as was the case with you.

      Men don’t like the social contract that requires them to pay, but they also want a woman to be interested in them. If you want to pay your own way, that’s fine, but you have to be able to show interest beyond that, to let the guy know that you aren’t just paying so that he’ll get the message and hit the road.

      • SS Says:

        Ok I have a question then.

        If men assume they have to pay… does a man not offering to pay always mean that he’s not interested in seeing the woman again?

        • D. Says:

          Put simply, in most cases, yes. You might find the odd guy who is very clear about being a feminist, but I would figure the feminism stuff would be made pretty apparent through conversation and/or profile text.

          But, assuming all parties are working within the unspoken social contract, then yeah, a guy who doesn’t pay is sending the same message as the woman who insists on paying: this ain’t happening, I just want the evening to be done with, and I don’t really care what you think of me.

          • fuzzilla Says:

            Makes sense. I don’t think I’ve ever had a man not offer to pay at all, but if I offered to split and he actually took me up on it, I took that to mean he wasn’t interested (assuming this is a first date – and most online first dates don’t work out, so).

            • SS Says:

              I’ve had it once – he asked me out a bunch more times but I’m not sure he was that “into” me. He was a weird one.

              • fuzzilla Says:

                Oh wait, there was the guy I met for a movie date. He got to the theater before me and when I got there said, “So, did you already order a ticket, or do you need to get one at the window..?” Way to make a gal feel special, dude. :/ (I always offer to pay and I understand going splitsies beyond the first date, but the man paying is the socially expected thing, and deviating from that Sends A Message to the woman that you’re not interested, it just does).

                • Jeff Smith Says:

                  If you offered to pay, I might take you up on it only because I might thing that I should.
                  Some women feel they should.
                  It would have nothing to do with how I felt about you.

                  • fuzzilla Says:

                    *Asking* me to pay right out of the gate as soon as he saw me was the real turnoff. But I wouldn’t consider petty shit about money a total deal-breaker, but it would be something I’d take note of as I was decided whether I wanted to see them again.

      • burnt Says:

        Social rituals are often ridiculous, but in the absence of true honesty in dating, I would readily embrace the deal your post implies–or some reasonable variation thereof.

        Cis-/heternormative fallacies notwithstanding, the interpreted routine first-date protocol would be as follows:

        1. Guy asks Gal on a first date, and assumes in good faith that he will be paying for all conventional costs thereof.

        2. Gal agrees to date in good faith (i.e. primarily out of interest in Guy, rather than in the expenses-paid experience), but is fully prepared to pay at least her own way under the appropriate circumstances.

        3. Guy pays for each expense without hesitation (not waiting for a “pump fake”).

        4. If Gal determines that she is no longer interested, she pays at least her half of the next presented bill as a means of conveying her disinterest.

        5. Guy respects Gal’s disinterest, and unless transportation issues reasonably preclude doing so, neither party bears any social obligation to further the charade, and will normally terminate the remainder of the date.

        6. If gal is interested, but wishes to assert financial independence, she shall say she’ll cover next time, implicitly conveying that she feels that there should be a subsequent date. Guy shall nevertheless proceed to pay this time, and both parties shall assume that Gal shall pay for (and, under most circumstances, ask out and plan) the following date.

        There are holes in this protocol when it comes to less conventional first dates, like the home-cooked dinner (this single parent’s favorite!), coffee and a walk, or other low-key, low-stakes dating, but we can burn those bridges when we come to them. For now, I’d just readily embrace uniform protocol and standards that don’t leave either party guessing when it comes to the check and what the payment means.

    • Parenting Says:

      Actually, there are many excellent restaurants in NYC and LA that are very inexpensive but people tend to prefer the trendy cocktail bar atmosphere over amazing Mexican/Indian joints for dates.

  5. bbdawg Says:

    If you’re dating someone I’d think pretty much after the 3rd date – you should absolutely split the bill. Unless the other person is really well-off meaning making 10 times more money or something and can afford to pay all the time, but that creates a power situation where the man is “taking care” of the woman which is a little bit more like an arrangement than a relationship.

    If there is a significant age difference or if the woman is extreeeemely attractive. (I.e. I doubt a guy would ask, say, Kate Upton or Miranda Kerr to split the bill, but then they only date guys who have money) I can see that going on for the entire relationship.

    • Wookie Says:

      Men who choose to date should understand their role in courting a woman. It is not to hook up but to show the woman he is interested in how he will provide for her. It shows the woman his ability to treat her well, to have patience, and compassion and hope for that the woman will deem him trustworthy enough to consider joining her life to his.

      • ATWYSingle Says:

        Oh, honey. No. You must be new here

        • burnt Says:

          It seems as though discussions of dating (and politics, sports, theology, morality, style, etc.) reveal a prevalent assumption that if I’m dating for X reason, then X is the only objective people should have in mind when dating. I have followed (and occasionally participated in dating hashtag discussions with) you for probably over 2yrs now, and appreciate that you almost invariably respond to questions and comments by addressing this assumption in two ways.

          1. You use “if ___, then ___” statements that steer people toward courses of action that suit their objectives, rather than doling out one-size-fits-all advice that ignores diversity of motives and circumstances.

          2. You address email/comment assumptions that imply that others are wrong if they do not consider dating objectives to be universal (e.g. that dating is necessarily supposed to be a means to eventually marry, or even just to enter long-term relationships).

          Anyway, this is a bit of a verbose response to one of your more concise comments, but the comment seemed an appropriate example of the tact that I felt warranted an expressing appreciation. Were I even ankle-deep in the dating world’s wading pool these days, I’m certain that your words would prove invaluable in application. Thank you for your voice, and please keep it up.

  6. Abby Says:

    i used to run into this a lot. I’m in the South. Some men will absolutely not let you pay. For a variety of reasons. Most will eventually. Here’s a few things I think work: 1) do as Moxie suggested and grab the check first and say “my treat!” And just do it. 2) you plan a date and tell him you’ve been having such a great time with him you want to take him out and treat him. 3) do something else for him that takes time and effort such as cooking him a meal, or taking him lunch. My now hubby used to complain about the bad coffee on his commute, there was no place on the way to get a good cup, so on a whim, I bought him a new thermal cup and a sampler pack of gourmet coffee. Cost about 20 bucks, but it made his day.

    Maybe he’s old fashioned and just feels obligated, if that’s the case, just make sure he knows you noticed and appreciate it. Things don’t have to be exactly 50/50. They just need to be acknowledged. My two cents, anyway.

  7. Nick Says:

    I have a three date rule. And I’m not referring to sex. I mean making an actual effort besides just showing up. If you don’t at least buy a round of drinks or help with some expenses (I buy the movie tickets, you buy the popcorn, it’s not rocket science) after three dates, I get bored really fast and bail. I’m tired of it. Picking up your bar tab every weekend is not my idea of dating. Put in some real work if you want a real relationship.

    • SS Says:

      This is my favourite comment in the entire thread:

      a) you’re not using your money to buy sexual favours (yuck)

      b) you (seemingly) refuse to give users a free ride, or the rest of womenkind a bad name.

  8. Kevin Says:

    i am newly single 50+ male and i expect to pay on the first couple/few dates. if the woman offers i will say no thank you. if its progressed to the 8th date (more or less even) and the woman reaches for the check i am very glad for the offer and accept it graciously.

  9. SS Says:

    I have a question for the menz:

    Does the frequency or level (amount of $$) a woman offers to pay/pays make you feel any different about her? If so, how?

    And.. if you like woman A more than woman B… does that make you more likely to pay and/or more happy to pay?

    • Kevin Says:

      i had a woman who reached for the check on the 3rd date and we both knew the check was more than what i paid for the 1st two dates but she absolutely insisted. I thanked her more than a few times.

      • Jake Says:

        Thanking her once should have been enough. It’s not like she is saving the poor as mother Theresa did. Or were you so shocked she paid, hence the gratitude?

  10. Jake Says:

    I think a lot of guys quit paying after they have been burned one too many times.

    Anyway, I believe that whether a woman offers to pay or not is a reflection of her character. It’s one thing for a woman to just sit there and expect you to pay compared to at least offering to pay. There are women out there who absolutely will not pay for anything EVER! Steer clear of them and their progeny.

    These days, I try not to pay anything beyond my equal share on a first date, etc. If the lady gets offended and won’t go out with me because of that, I can deal with it. So far, I have gone on a few dates with my date paying most of the tab. Coupled with the fact that I meet them around my place has made dating enjoyable for me once again.

  11. Andrew Says:

    You hit the nail on the head this time.

    It’s really very fake to offer to pay, after the black leather bill fold has arrived, and you haven’t made any effort to pick it up. Guys know this very well. It’s better to not even offer, than to be creepy about it. (Yes, women can be creepy too). Anyone who wants to pay, does it without asking. Even if he puts his credit card on the table, you can put yours down too, and ask the waiter to split the check.

    Guys know how to test also. They want to know if you will bleed them dry, if you are entitled, if you see them as a meal ticket or a sugar daddy. They start losing respect for women that take advantage. In this age of equality, when women have careers and expect to be paid the same as men for the same work, waiting for a man to pay all the time means you’re a freeloader.

    And if you are not interested in the guy, but still let him pay, means you’re a b—-.

    • Parenting Says:

      I think its disrespectful to reject someone’s generosity by pulling out your card and throwing it down after someone has already put theirs down. Maybe its cultural, but I wouldn’t do that to my friends or family and would be put off if someone blatantly rejected my generosity by insisting on splitting the bill. Once the card is on the table and someone says “I’ve got it”, my response is, “Thank you for dinner! The next one is on me.”

  12. Sarah Says:

    This topic is of great interest to me. When I accept an invitation to meet, I am very careful not to ask for more than one drink ( and always order house label because it’s cheaper). Also, I never order anything else even if I am starving. I went on this date with this guy and although we got along great there was no chemistry for me and I knew I would not ever go on another date with him. When the bill came, I did not offer to pay. He paid, I thanked him for the drink and his time and we went home. A few days later, he sent me a message saying how offended he was that I did not offer to pay and for this reason we would not be a good fit. I smiled and I answered, “I AGREE, BEST OF LUCK TO YOU”. Than, another time, I went on another date with this guy,( so as not to offend him) I offered to help him with the bill. He replied quiet offended that I wasn’t letting him be a gentleman. So its confusing to know what will be acceptable or not acceptable when it comes to picking up the bill on a date. I am of the belief that whom ever offers the invitation to meet first, should pick up the bill. I agree with Abby, if your date keeps picking up the bill and won’t let you pay, surprise him by making arrangements ahead of time and take him out where everything has already been paid by you. Or excuse yourself to go to the ladies room and stop by the waiter to give him your credit card so the bill will be paid before it reaches your table. After the first 3 dates if the girl doesn’t do something equally nice for him, it could very well be that she is just looking for a “Sugar Daddy”!

    • ATWYSingle Says:

      Every adult person knows the right thing to do in that situation. I don’t buy this whole thing about how its so confusing when the bill comes. We know the right thing to do and consciously choose not to do it.

  13. Wookie Says:

    Up here in the North East, men and women have chucked social norms, which allow for a lot of confusion. Men wanting to treat women like men. Women wanting men to treat them equally, as men. Sheer stupidity, short-sightedness and men who have no idea how to respect and value women other than sex objects.

    In the South and Southwestern parts of the US, the men and women have been taught that women are different and that there is beauty in that difference that should be respected and protected. No one is thinking about gold-digging because men and women both have a choice in who they accept a date with. Men have self-respect and show it and how they respect their date by how they treat their date. Men who choose to date, choose to woo or court the woman the want to be with. It is the woman’s job to show that she is worthy of his respect by the choices she makes and how she uses her feminity. You should ask yourselves is this how you want to be treated for the rest of your lives by a grudgingly, cheap man who keeps score? Or, by a man who values his own self-worth which is evidenced by how well he treats and lifts up the woman he is dating as well as others?

    Also, if I’m spending big bucks getting ready for our date the least a man could do is buy a cup of coffee or a meal. What an insult to ask a woman to pay for a date when she’s already spent 100’s if not 1000’s (depending on the event), to prepare with hair, make-up, mani-pedi, dress, shoes, jewellery, purse and accessories.

    Now, once you are in a committed relationship, that is when you can spend your money on him not before. I love giving my man little gifts and big surprises that I know he wants. However, I will never emasculate a man by taking away his ability to show me how well he can provide for me. It is a very strong, feminine thing to embrace. And, good men get really turned on when you embrace your feminity while allowing him to honor his masculinity.

    Just my two cents but I would never degrade myself by spending time with the men on this platform or the men that are mentioned in here. They have no game.

    • Larry Love Says:

      “Just my two cents but I would never degrade myself by spending time with the men on this platform or the men that are mentioned in here. They have no game.”

      but you troll this website.

  14. RedNeckGeekGurl Says:

    Ahh … Wise Wookie … Now I know what I have done wrong all my life. Never pretended to be a Barbie prize … Never spent that kind of $ preparing for a date (or any other life event! Excluding first wedding maybe). If I had – I could be like you! Quid Pro quo is how it is termed I think … In the polite SouthEast.

    So – do tell about the amazing man in YOUR life who responded to your amazingness!

    From a whole different galaxy far far away ….

    • SS Says:


      I live in the south east and apparently *I’m* in a whole different galaxy too!

      Maybe it’s because I don’t spend $1000 getting ready for a date… mybadz.

  15. Joe90 Says:

    I’m out with friends, I say “I’ll get this one” end of story, if someone want to chip in they will, “no no, I’ll get this one”, OK. That’s how it works.

    Let’s go halves at the END, yeah, now if had that I sweeden were its expected and refreshing because you know she’s not wasting your time burin the Anglo world it’s pure fake. Also 8 dates, no sex, yeah you are a freeloader.

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