By Baila Sebrow


I started dating a man who is a little older than I am. In the beginning I was not that happy about our age difference, but my shadchan convinced me that I will get used to the age difference. It took me a while to get used to his wrinkles and jowls, but with time I started appreciating him for the way he treated me. He is established and also extremely generous with me. No man my age would have ever bought me such expensive gifts and taken me to such fancy restaurants.

But with time things changed. He has a few cars, and now he picks me up in the not-so-cool car. The way he used to wine and dine me also slowed down, and he now takes me to cheaper places. He still acts like a doll to me. He always offers me food and snacks when we are out together, but why did he suddenly change? He is still just as rich as he was.

Things are getting serious between us, but now I worry that he might be getting cheap on me. My friends with whom I spoke about it agree with me. I could never be married to someone who is cheap, or I would have married a man my own age a long time ago. What do you recommend that I do?


Upon reading your letter, it would be easy to quickly conclude that you might be unreasonable as it relates to men and the way they choose to spend their money on you. But I believe there is much more going on than a frivolous complaint that the man you are dating is no longer spending as much money on you as you would like and as he had done previously.

Just so you know, the way a man dates, in terms of spending money, is not necessarily indicative of how he will treat his wife after he is married. There is no perfect science to determine how generous a husband will turn out to be. A man can act like a spendthrift while dating, and after marriage he can be as frugal as they come.

Dating is not a perfect skill. There are no handbooks or guidelines to follow, because there are variances in personalities, and one cannot predict how the other will react.

Here is what I think might be going on in your situation. This man must have been told that you were not too keen on dating him because of the age difference. And I have a feeling that if you shared your complaint with the shadchan about his wrinkles and jowls, he felt compelled to go the extra mile in order to impress you.

It sounds like he is a man of financial means, so taking you to upscale restaurants and buying you expensive gifts did not break his bank. But how long can anyone keep doing that even if he can afford it? The best spouse in the world will not come home each day of his married life bearing pricey gifts for his wife.

In many cases such as yours, where the man starts off spending lots of money on the woman, he typically feels that he needs to increase the expenditures to further impress her. Eventually, it can begin to weigh on him and turn him off altogether to the point that he no longer has any interest in continuing to date the woman. And what happens is that he will slowly slack off and find a reason to end the relationship.

Scenarios of that nature happen because he either gets bored with the woman when he realizes that he is an ATM to her, or he comes to acknowledge that he may have gone above his financial means, which could have originally been overestimated by the woman. In your case, it appears that you may have made such a favorable impression on him that he no longer feels the need to impress you and instead wants to focus on getting to know you better; he may want to advance the relationship to a deeper level.

I always advise men in the early stages of dating to spend as little money as possible, because doing otherwise can result in feelings of disappointment on the part of the woman, as in your case. No man should ever be expected to continuously spend hundreds, if not thousands, of dollars on a woman early on. And when a man insists on doing that, it’s enough to be considered a red flag.

You are experiencing feelings of withdrawal, and you are apprehensive about continuing the relationship. It is disconcerting to hear you say, “I could never be married to someone who is cheap, or I would have married a man my own age a long time ago.” What kind of talk is that? And do your friends agree and encourage such a mindset?

I never fault a woman for expressing that she wants a man who is financially secure and who can take care of her, any more than I fault a man for saying that he wants a young, beautiful woman. People have the right to want whatever they want. Whether they get what they want is a whole other story, and usually that’s where mazal comes into play.

In the case where a woman wants a man who has a lot of money, she will usually agree to date somebody who is a few years older and more established than a younger man. However, referring to him as a cheapskate because he is not wining and dining you according to your expectations anymore is out of line.

It’s not as though he stopped taking you out to eat altogether. You say that he offers you food and snacks. He is considerate of your feelings and is making an effort to get to know you better. Hopping from expensive restaurant to more expensive restaurant is hardly the ideal progression of seriously getting to know one another.

He may not be spending crazy amounts of money on you, but he is spending something much more valuable and irreplaceable — his time. Many women do not realize that when a man plans his dates, that involves time, too. Researching and organizing outings of any type to ensure that his date will enjoy herself counts also as his time being spent. Every effort that this man is making on your behalf should be considered as pricey, too. However, at this point, to you he no longer represents that prince on a white horse.

From what you said, it comes across that you were seeking a man who has a lot of money to spend on you, and that you expected to be treated like a princess. Your shadchan may have known this about you, and that is why he/she suggested him to you in the first place. Yes, it took convincing to get you to agree, but not only did you agree, you developed a sense of entitlement that you deserve all that he gives you and more. Perhaps to you is he is not as handsome as you’d like, but his resources make up for it.

The problem here is that your focus of your opinion of him was not on who he is to you or the type of character he possesses. Rather, you viewed his exterior, and you never allowed it to flourish into more than that. You are not questioning whether he is capable of being a loving spouse; your concern is whether he will be that prince for you.

In the early stages of dating, things were going well because you appreciated the fancy top-of-the-line car that he took you in when he wined and dined you. Nowhere in your letter did you make any mention of his intellect or personality. We don’t know if he is a nice person, and I believe that you don’t even care to know. All that matters to you right now is that you feel cheated. The only thing that has changed is the amount of money he now spends on you. You see this shift as a negative pattern that will continue should you allow this relationship to go on.

Dating is not an easy parashah to experience. Most people, including men, experience various trials and tribulations when they are serious about finding a spouse. The problem you have presented is definitely a big one, but it is you who needs to alter your behavior. I am not blaming you in any way, nor am I invalidating your feelings and concerns. However, you need guidance to help you understand the important aspects to seek in a potential match.

If it is only money that you seek, that is your prerogative, but you also need to understand that there are men out there who pretend to have more than they really do in order to find a woman who wants a rich man. It is possible that is the case here, too. Or it could be, as I mentioned earlier, that, yes, he has all that you want materialistically, but he cannot keep on giving you and giving you while he dates you.

I understand that you are also bothered by the car he now drives when he picks you up for dates. It could be that the car he used to drive may not even be his. Believe it or not, there are men who borrow or rent luxury cars to project the image of wealth. It could also be that he has more than one car, and he may not want to drive the most expensive one because he is concerned about parking it in spots that may not be safe. He may have done that in the beginning stages of dating, but now that he feels so comfortable with you, he is relaxing a bit in that area. Nevertheless, you don’t care what the reason may be. Again, he no longer represents what you were looking for.

I urge you to express your concerns to the man. I have no clue how he will react to your complaints. But you are not doing yourself or him any favors by keeping mum about how you really feel. If you are not comfortable doing that, ask your shadchan to communicate your feelings to him. I hope that he/she will express what’s going on with complete accuracy, including not just what you are relaying, but his response, too. That’s why I suggested that you should be the one who talks to him. Either way, there is the likelihood that he may become completely turned off when he discovers what you expect from him and this relationship, and especially when he hears about your criticisms.

Maybe he’ll have a favorable reaction. It might turn out that he likes you so much that he’ll do whatever it takes to continue indulging your expensive tastes in the manner that you expect of him. If so, it would seem you have met your match!

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis and shidduch consultant. She can be reached at Questions and comments for the Dating Forum can be submitted to


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