2040. Single Women Don’t Pay — I

Her Highness That Horse is Dead inquired at post 1661. “Would it say something about a man’s strength of character or motives if he did allow a woman to pay [when the bill arrives]?”

Yes, it would. Perhaps only questionable but it’s a pole on which a red flag may later fly. My reasoning works like this.

  • Not his words but his actions program his heart. When he doesn’t do things that he figures he should, his mind uncovers avenues of how to escape other obligations or responsibilities. The more he talks her into paying, the worse for her as the action programs his heart with the possibility that he can take advantage of her.
  • Her greatest need is for a brighter future, which means his role should have these features: 1) She can depend on him, which requires that he show himself to be reliably responsible. 2) His sense of duty is only as strong as his integrity and devotion to her. 3) Her best insurance for the future rests upon his integrity, his insistence on doing the right things and doing them correctly—with emphasis on doing rather than saying. 4) The right things are those that prove that he’s worthy of her and capable of helping and willing to promote her hopes and dreams—not just his.
  • Whether she pays part or all of a bill, it’s the same. It violates her interest and enhances his. She may be pleased and financially more able to be of help or show her appreciation. However, by doing so she teaches how easy she is to dominate or play against her best interest. She indirectly hints that she may be weak or a pushover and he can get his way on other things. Thus, she plants the seed of future discord by not establishing her standard, by not displaying her expectation that she’s worthy of special care if he hopes to win her heart, and by not holding him to account for his words of interest or affection. His actions cure her doubt. Her expectation that he pay cures some curiosity about her strength of character, which earns his respect.
  • Each crack in his integrity before marriage inevitably widens afterwards. If he’s willing to let her relieve him of a duty, a responsibility, she can’t depend on him to do the right thing in her future. What is the right thing? He has to prove himself worthy of her. When she volunteers to pay without emergency reason, she follows her mind instead of her heart, lowers her standard, and lessens the possibility that he will prove himself worthy of her expectation for their future.
  • She can easily infer that if her guy is generally weak on duties and responsibilities—eagerness to pay on dates is but one example, it easily translates to less than ideal integrity, which doesn’t bode well for her future.

When he continues to pay in dating and courtship, that and his other actions compound in his heart and he becomes more favorable to, for, and about her. He starts doing things to please himself that he’s pleasing her. Out of that, his devotion grows. Smart women insist on seeing devotion instead of giving all in exchange for a guy’s words of commitment.

Consequently, except in an emergency, let his ability and willingness to do the paying determine where, when, how, and why they do whatever they do together. If she can’t live with the results, she invites difficulty living with him as husband.

It should make no difference that she has greater income than he. As the relationship expert, she can find ways to use her extra money to brighten their marital future, if and when it arrives. But that’s another story.



Filed under courtship

21 responses to “2040. Single Women Don’t Pay — I

  1. prettybeans

    Hello Mr. Guy,
    I hope that you are well today.

    Thanks to your thoughts today, I am once again reminded of how important it is to be patient and to hold back in order to allow myself adequate time to observe how an interaction develops. In the past I have observed that I am usually rather too eager to cover-up this deficiency and this ends up making me feel like the man I am dealing with is weak..(even though I offered to go Dutch or to pay the bigger portion of the bill).

    I think that what you say is true – It may not be a deal breaker but it is certainly a baby-step towards an unfavourable outcome as far as the woman is concerned.

    I am most interested in this part:
    “It should make no difference that she has greater income than he. As the relationship expert, she can find ways to use her extra money to brighten their marital future, if and when it arrives. But that’s another story”

    Could you kindly expound on this a little more? And specifically whether in your opinion and experience dating a man with less income is a bad idea. And when/how is one to establish this.

    Thank you and have a lovely day

    Your Highness Prettybeans,

    You ask if dating a man with less income is a bad idea. No, not bad but it’s a slippery slope. He eventually resents it silently if not outwardly and resentment shows up in other marital arenas.

    I need more time about “another story” so come back tomorrow.


  2. surfercajun

    This spoke more to me than the woman paying….in a nut shell. relationships that form between men and women before and after marriage.

    Thanks, Sir Guy for this eye opening thought.

  3. My Husband's Wife

    Wow, beautifully explained! What a great article on this subject. It’s funny, but 20 years ago in my dating life I was really confused on this, but knew instinctively that the man should pay–but societal pressures pushed something difference. So I adopted a hybrid of traditional/modern style of dating: When I would go out with a guy who I liked only as a friend, I paid as I wanted nothing else from him than just “friends”. BUT when I considered the man to be husband potential, I let him pay. (NOW I know in all cases I should have let them all pay as all of those men were “potential” husbands. Thank goodness I immediately put my husband in the “Mr. Potential” category or else I would have been paying for dates with him at the start!).

    I do have a question. Would the following reasoning also be true? (Following the same reasoning as the article indicates?) A man who asks a woman to shack up instead of marrying him shows him to be weak on responsibility and changes how he sees her (a pushover/less respectful) if she decides to live with him without marriage. And that would be why most of the live-together-first relationships usually end up in divorce or the marriage never happens at all? In other words: When she decides to shack up instead of marry, she follows her mind instead of her heart, lowers her standard, and lessens the possibility that he will prove himself worthy of her expectation for their future?

    Your Highness My Husband’s Wife,
    To your first question, yes, absolutely. Your last sentence is accurately phrased. Thank you, well done.

  4. Cinnamon

    “Would it say something about a man’s strength of character or motives if he did allow a woman to pay [when the bill arrives]?”

    Sir Guy,

    Thank you for a wonderful article explaining the reasons why and this strategy works – by programming his heart to become the man she wants him to be, and the man HE wants to be. Just one minor point of disagreement:

    If a woman makes the mistake of opening her handbag and pulling out her wallet on the first date and the man doesn’t stop her, I believe that it is a mistake to AUTOMACIALLY draw a negative inference. As you have mentioned previously, men are confused about gender relations and how it impacts etiquette, and do not wish to risk offending the “modern , independent woman.”

    Just as some men will hesitate to open a door for a woman they don’t know for fear of being repriminded – (“I can open my OWN doors, thank you!” – smirk) – I think the same confusion and desire not to offend (or even worse be deemed “sexist” or “patriarchal”) could apply to the man who allows the woman to pay on a date.

    I agree it is a potential red flag, but it might also be the result of the confusion I explain above, and in the latter case, I think it really tells us nothing about his character per se apart from the fact that he is confused by this mixed messages about ender roles that are sent out by most women today.

    Which is all the more reason for the relationship experts to follow your instructions, thus avoiding entirely that awkward moment when the check arrives!

    A man who EXPECTS it – now that is a different matter entirely, and obviously a red flag to put him right back into the parade!

    Your Highness Cinnamon,
    Good comment and questions. Come back tomorrow, outta’ time today.

  5. KitKat

    The first date, especially if it’s more a “formal” date I think the man should usually pay, after that I don’t really see why the man should always pay 100% of the cost of dating. The only problem I see would be if the women was always paying, that would be the real red flag to me. And even worse she’s loaning money for his living expenses, now that’s a red flag. But splitting the costs of dating, especially causal dating, really can’t see problem, especially when neither have much money. Or if expecting the man to always pay, then I wouldn’t expect the expensive dates.

  6. Some Other Guy

    I would caution you all on this. I would always pay for at least the first date. But if at some time during the dating process, the woman did not offer to pay for something, anything, I would start to dismiss her as too selfish and entitled to consider for long term potential. Or at the very least I would start to suspect that she was not as interested in me as I was with her. And I would start to distance myself from her. Even if she were giving me verbal approvals. If she didn’t chip in at some point, no matter what she would say, I always understood that actions speak louder than words. If she’s not contributing, she’s not interested.

    This is but one man’s opinion and I realize your advice is for women. But had my wife (26 years) not chipped in at some point, we would not be married now.

    • Etu

      Interesting perspective. I have bought a boyfriend a gift for the holidays, have baked things for them etc, but am careful not to let any bought gift to them outshine their gift to me. Like My Husband’s Wife above, there is just something very natural about the guy paying and if I got the impression from a boyfriend that I should pay for something/anything, at any point, I would very much resent that and probably seethe! Some might mistake that for a golddigger type mentality but I think a girl can put better effort into the relationship in ways other than paying for stuff. Thats just my opinion though!

      • Some Other Guy

        Making food for your man is perfect. Very attractive.

        • Cinnamon

          Sir Guy said something similar recently about the way to a man’s heart is through his stomach. Would you explain the thinking behind this from a man’s perspective and how it effects his perception of her?

          Does it change if he is a good cook (not professional) himself, as some men are?

          • Some Other Guy

            You cooking food goes to one of those caveman instincts. It is womanhood at its finest and is just intrinsically attractive. It is your gift to him that comes from you and only you. It speaks to him at the same level as when he sees the curves of your body. It is a very primal kind of feeling. And I don’t think him being a good cook would take anything away from his appreciation of you cooking for him.

            Here’s another example. I taught my wife how to cut my hair using clippers (like they do at the hair salon). It is actually quite easy to do with a hair cutting kit from CVS or Walgreens. Initially it was just a way to save a few $$. After a while though, she started cutting our kids hair too. Sure we’re happy to not pay the salon $25 per cut. But what was unexpected was how hot it is have her cutting our hair. It is just very sexy to see her taking care of the family like that.

            • Cinnamon

              Wow – thanks! That is really interesting. You’ve demystified a lot about the saying that”the way to a man’s heart is through his stomach.” I think I finally understand it now.

              He is a better cook than me, but I have a signature dish he loves. I do cook this for him regularly and it does seem to make him very happy.

      • My Husband's Wife

        Interesting perspectives here. I agree too, that modern men could be so confused as to what to do with paying for their date as women’s attitudes are different from one girl to the next.
        Could you also view it as this: Be such a woman that the man is inspired to be the payer (provider)? Meaning that she’s a delight to be around, she’s attractively groomed for him, modest in attire and expectations about spending etc. and does those nice things such as make dinner, etc. Also, like MLaRowe mentions below: be a woman who enjoys the little things and who doesn’t have to be showered with extravagant gifts all of the time. Be appreciative and respectful of his finances. Have him see this attitude so that the man doesn’t feel any resentment or see the selfishness that Some Other Guy mentions might creep in after a while.
        Therefore, it’s a “balanced” relationship so that neither party feels taken advantage of, but they each have uniquely different roles in dating–just as in marriage. I’m just thinking aloud here…

      • gonemaverick


        i like how you think *wink*

    • MLaRowe

      Some Other Guy, to affirm what you are saying my husband has a bad memory of dating a woman in college who never chipped in at all. Ever.

      They dated for long enough that she could have at some point thought of his wallet. I think he still feels he was “used” by her.

      In the initial stages of dating though he would not let any woman pay. It is just his way. I could certainly see some women taking advantage of that quality in a man.

      • Cinnamon


        Thanks for adding that perspective.

        My Mr Goodenough had exes who depleted him both financially and in other ways, giving back nothing. He doesn’t complain about it, but I know it has effected him. The recent statistic I read is that men will lose an average of 80% of their net worth in a divorce.

        I will pay maybe 1/8 of the time on dates, usually by picking up tickets for a play or concert. On a rare occasion when I pay for lunch or dinner I will always tell him I would like to pay this time ask him first if it’s okay. He always says yes.

        I am eager for Sir Guy to weigh in. I understand and agree with the principles he presents here, but I think there are perhaps more nuances involved than what the article considers, particularly when it comes to divorced men who are struggling to support two households, and who do so without complaint.

  7. MLaRowe

    This subject makes me so grateful to be married.

    I’d be glad to go to less expensive places or simply out for coffee or a walk with an ice cream cone. If money was really an issue a picnic or free concert could be fun and I would never bring up the fact that it cost nothing. I would try very hard to be positive and easy to please.

    When one is dating they are trying to get to know another person and that doesn’t need to cost very much. Still, I think the man needs to initiate all of this.

    I once worked for a florist and a handsome man came in and he was clearly in love. He was taking his dream girl out to dinner for their first date and wanted to bring her flowers. He carefully chose each flower for a small unique bouquet. As I wrapped them for him he told me which restaurant he was taking her to. It was a modest Indian restaurant but still a rather romantic place. Those actions (not the cost) told me how carefully he was orchestrating his date and how much this girl already meant to him.

    • Some Other Guy

      Yes, you are very right. #1, The man does need to initiate and lead things. A man that does not act as leader in the dating phase is going to be a disaster as the relationship goes on. #2, In early dating, less expensive is actual better than extravagant. The high cost activities puts way too much pressure of expectations on both parties.

      • surfercajun

        first date with spouse was a picnic… I was more impressed by that than reservations… at times I wish I would have offered to bring something. …even thought I never offered to pay for a date I did offer money for gas. Does that count? 🙂

  8. Felicity

    Sir Guy, please comment on these comments when you have a moment. We await thee! Xx

    Your Highness Felicity,
    Be glad to but what comments might that be?

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