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DATING MAZE #296: Dating Sabotage
Dating Advice 296

DATING MAZE #296: Dating Sabotage

Date after date, she’s setting guys up for failure.


Dear Rosie & Sherry,

I have a considerable record of short-term courtships with men over 30. Despite the fact that many of them say they're dating for marriage and seem interested in pursuing a relationship with me, I am often disappointed by what seems to be their greedy approach to dating.

These men earn average-to-high salaries, yet they willingly accept my offer to pay my own share of the restaurant tab, which I do just to be tactful. I always wonder whether they will accept the money, and then the shock comes when they do. I always feel embarrassed and even humiliated at the fact of that we're merely going Dutch, instead of having a real date.

Is this normal behavior for men? Should I immediately break up with a “non-gentleman” who accepts my offer to pay, even though he has some strong points that I appreciate? Should I continue to date and try to talk to him about this, or should I look for other men to date?


Dear Jeannie,

We are curious why you would offer to pay your own way on a first date. You say you do this to be tactful and that you really want the man to decline the offer, but we wonder what your real motivation is. It is possible that at the same time you are looking for generosity in a man, you are uneasy about accepting his generosity.

The reality in most Western countries is that it’s still considered appropriate for the man to ask the woman out, make the arrangements for the date, and pay for the evening. That's what your date expects to do when he asks you out. When you offer to pay, you give him a message that you don't view the date the same way he does. And when he accepts your offer, you turn the tables and are hurt that he's doing exactly what you suggested that he do.

He's simply being polite by following your lead.

When that happens, you decide that he's mean, ungentlemanly or unromantic -- even though he's simply being polite by following your lead. He doesn't know that you secretly hope he'll say, "Nonsense! When I take a woman out, I pay the tab."

Instead, he may decide to accept your offer because he's flattered by it; or because he likes a woman who is more assertive and independent; or because he thinks you're more comfortable paying your own way; or he's relieved that you have the sensitivity to understand that he pays for dates all the time, or any other reason.

There's another aspect to your practice that you may not be aware of. By offering to pay your way at the same time that you hope he will decline the offer, you're unconsciously testing him and actually setting him up for failure. It's not fair of you to expect a "real gentleman" to turn down your offer, especially since you may make that offer in such a way that he feels he's a real gentleman by accepting it.

This is called “sabotaging the date.”

So where does that leave things? If you want to get out of this pattern, and begin to move forward into a relationship that leads to marriage, you will need to do some serious introspection to figure out what’s behind your feeling that you have to offer to go Dutch, resenting a man who accepts your offer, and secretly wishing for someone who'll act like Mr. Chivalry instead of acting like a regular guy.

Could it be that you feel you're not worthy of having someone pay for your dinner or your coffee?

As a first step, we suggest that you find a happily-married friend or acquaintance who can be your dating mentor. It seems to us that you'd genuinely benefit from having someone who will listen to your concerns and can offer some helpful suggestions from a “successful relationship” perspective.

In addition, you may want to consult with a therapist to explore any more deep-seated reasons why you are setting up these men for failure.

Until you’ve done some of this work, it is probably a good idea to take a brief break from dating, so that you can come back with a fresh perspective.

And we recommend that in the future, you let your dating partner play the traditional man's role when he takes you out. There are better ways to learn about his character than playing games or creating "tests" that only you know the answer to. As your relationship develops, you can learn a great deal about his generosity, ability to give and share, and attitudes toward other people by observing how he treats you and others around him; asking him questions that encourage him to talk about his values; discussing what's most important to each of you in your lives; seeing how he interacts with his family and his and your friends; and comparing what he says, to what he does and hopes to do in his life.

We wish you success in navigating the dating maze.

Rosie & Sherry

November 21, 2009

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The opinions expressed in the comment section are the personal views of the commenters. Comments are moderated, so please keep it civil.

Visitor Comments: 26

(26) Anonymous, February 12, 2013 5:00 PM

I dont know how to date

I feel very uncomfortable about the money issue and I am fearful that another kind of payment is expected. I would really like to get married but ... at this point I don't see it happening.

(25) AH, January 7, 2013 4:25 AM

I think she is right.

No, she is right. Guys today tend to treat women like guys. It is really a turn off. Pay for the date for crying out loud. Act like a man without prompting. Have a little class. It is polite to offer and it is even more polite to pick up the tab for your date.

(24) Santa, November 16, 2011 7:06 AM


I am older, single and have many friends with whom I will have coffee, dinner etc. My viewpoint have been that if I go out with a platonic friend we each pay our own bill, or halve it, same as when I have dinner with a female friend. But if I go on a date, I will allow the man to pay on the first date - after that we as a couple will decide how and who pays for what.

(23) Joe, October 17, 2011 5:18 PM

What's wrong with her paying?? I don't get it!

I am a guy and I think it's fine for the girl to pay half if she wants to. I actually like it sometimes to be honest. I consider myself to be a generous person, but I don't see why the man should be expected to pay all the time. Firstly dating is expensive. Secondly, today most women work and often on high salaries. So what's the big deal if you go dutch? I don't believe I have never insisted on paying because I am a gentleman, but I think the whole protocol thing is ridiculous. Frankly I've been on so many dates where the girl doesn't even acknowledge you paying or even give a proper thank you, that it just puts me off completely. In contrast my last girlfriend would secretly buy drinks for both of us on the way back from the bathroom, because she knew I would insist otherwise, and she genuinely refused my money with none of this false modesty nonsense. Now this is true derech eretz! Men don't like gold diggers and they don't like manipulation. My advice is be honest, if you are not interested in paying don't offer, if you are, then just pay in the form of a present and don't make a deal out if it. It can be emasculating for some people if the woman pays, but a present is a sign that you genuinely care. Another thing is I think it's crazy to judge a person on this criteria alone. Even if a girl (and it's happened alot!) doesn't say thank you when I pay, I try to judge favorably and say to myself maybe she is embarrassed about these things or this is how it's done in her culture. If I see the same pattern in other situations only then I start to make assumptions. In my opinion if you want to see if he has a good heart and is generous, see how he treats his mother.

(22) rob, October 5, 2011 2:12 PM

Stop playing games

Ladies, don't make an offer to pay or split the tab that you don't intend to or want to fulfill. It's insincere at best, and manipulation at worst. It's confusing to a man to try to read your mind as to your intentions. Men have traditionally paid for dates because they were expected to extend the invitation. This is social etiquette, but not related to dating: He or she who invites somebody else is expected to pay, because the invited party is considered the guest. Simple as that. If a party invites another and doesn't or can't pay for the activity, then it's a warning sign; either the host is clueless about etiquette or living beyond his/her means.

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