Rule #4 – Don’t Meet Him Halfway or Go Dutch on a Date

Who pays for the date gets to the core of the loss of the script and can elicit uncomfortable feelings. Some men get offended when women offer to pay for their meal, others are offended when they don’t. What’s a girl to do?

The Rules say that women should not pay for anything on the first three dates. The Rules would definitely disagree, but 0n the first date I reach for my purse when the bill arrives. If he is OK with spliting, I loose any interest in seeing him again (tho typically I’ve already come to that conclusion anyway). It’s not a matter of entitlement or punishment, it’s just a natural reaction that means “this guy is lame”.

Men, if you’re wondering why you should pay for dates, here’s why:

1. It shows that you have financial resources and that you are willing to share those with a lady.

2. It makes the woman feel special and taken care of.

3. Friends split the bill. If you’re interested in being something more, going dutch sends the wrong signal.

4. If you feel resentful of the money you spend on dates, that shows that you’re probably Just Not That Into Her.

5. If she doesn’t express appreciation, that’s a good indication of her character; that she feels entitled.

Consider also that to prep for dates, women will spend money on makeup, manicures, pedicures, dresses, skirts, hair removal, and the salon. Women spend money on one or more of these things because if they are into you, they want you to be attracted to her. (Doing these things also make women feel better about themselves which will help their confidence during the date.)

If women spend money to impress men by the way they look, then it’s really not fair to expect women to pay for their meal or ticket to a show. That means that they ends up spending more money than the guy for dates.

Once the relationship is established, it’s OK for women to pay for coffee, or pay for the meal or cook on special occasions. But whereas women feel special and taken care of when a man pays, when women take upon the role of spending money on men, it doesn’t make them feel the same way. When men are really into you, they’re going to enjoy making you happy by taking you out. And when women have to play the role of treating men they become resentful of having to chase men and spending their finances to court him.

A lot of women make more money than men, especially in their 20s. What to do about this imbalance? I think it depends. If the guy is poorer because he’s in a low-paying job that he loves or he’s in school, the fact that she makes more shouldn’t necessarily make her pause, but she shouldn’t expect fancy dates very often. If he’s poorer because of lack of ambition, that’s a red flag.


Tucked into this chapter are a few paragraphs telling women that men will go out of their way to see them if they are in to you. This has very much been my experience. Even if you live in an inconvenient part of town, he will come pick you up. If he doesn’t or he complains, He Just Not That Into You.


P.S. If you’re dating a woman and she doesn’t make an effort to doll herself up, she’s Just Not That Into You.



Filed under Book Reviews, Dating, Female dignity, Men, The Rules

7 responses to “Rule #4 – Don’t Meet Him Halfway or Go Dutch on a Date

  1. I’m wary of “The Rules” in general, but this is solid.

  2. Pingback: Linkage | Datingwise

  3. I don’t know that I agree with this rule. In fact, I am sure that I disagree. I will agree that, assuming the man asked the woman on a first date, then he should pay the bill on that date. Where it goes from there depends on the response you get from her. Any indication that she wants to take it slow or be just friends, the automatic response should be to give her what she wants and set up a Dutch date. The alternative, to try to impress her even more by throwing good money after bad, is the absolute wrong move to make. This is my current hypothesis anyway…

    • Rae

      I disagree smoothreentry…. The man is the pursuer.. If he expects a decision to ne made after one date then his lost. If hes ecpecting something after one date his lost.. She doesn’t have to give him any indication that she wants to be more than just friends, she doesn’t know him well enough to make that kind of decision.

  4. I’m a man who has always felt resentful about the idea that a man should still pay in modern times. I will say your arguments why are well reasoned and it does make sense about women spending money to look good for me.

    Much more convincing than the insulting and nonsensical stuff I usually hear when I ask why it should be that way.

  5. I’ve got a question. Say a guy pays for just the first date and then always went Dutch on every other date after, how does one deal with that? I understand that as the lady , you could always walk away from that guy because of that. However, I do not feel like it is a strong enough reason to not pursue something with someone but at the same time I feel like it is an indication of how invested he is in you. Moreover, it really has nothing to do with the money to be honest. I could cover the entire bill if I wanted. It’s about knowing that someone cares enough to take the initiative the first few times. I would personally start offering to get the bill after he paid about 3 to 4 times. It’s more about the principle. So if you wanted to address this issue with a guy who has only paid once , any advice on how to go about this? Mostly because it is a sensitive conversation which I’d only want to have because I wanted to pursue things with him regardless. I ‘d just like to get the whole ‘ how could you not take initiative by paying the first few dates’ off my chest.

    • Whoever did the asking out should pay. Going Dutch is what friends do. The burden shouldn’t be just on one member of the couple to be planning dates; after 3 dates it’s perfectly acceptable to start planning them yourself.

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