By Baila Sebrow



I am a gentleman nearing retirement, and I’ve been looking to remarry for a few years now. I am not ashamed to say that I am looking for a woman who is young — at most in her mid-forties, but only if she is absolutely gorgeous. I am not going to lie and tell you that it is because I want more children. I am not like other men my age who lie about their age or tell matchmakers that their rabbi gave them a psak to have more children and that they need to marry a much younger woman.

You see, Mrs. Sebrow, I am just not attracted to women my age for many reasons. I want you to know that I don’t have a problem finding young women, even though some matchmakers get mad at me. Some of the female matchmakers are nice, and they tell the women they introduce me to that I am younger, but I don’t like that because I am upfront and honest and I would never lie to a woman.

I am very handsome for my age, I have a full head of my real hair, and I am financially secure. I want to spend the rest of my life with a beautiful woman at my side. I am not asking for your blessings to do that. I’ll tell you what my problem is. Like everyone else, and especially because of my age, I cannot risk catching COVID, so I rarely leave the house, except to take out my garbage. As I said, I am a man of means, so I get everything I need delivered to me.

My problem is that I am meeting women now through dating apps, and then we chat online. How can I know that they look the way they seem? What I mean is that I find that Skype or FaceTime will not show wrinkles or blemishes. When I meet them in person one day, suppose they do have wrinkles and blemishes that I could not see for the last several weeks? I don’t want to hurt anyone, G-d forbid, and break up with someone because I don’t like the way she looks.

It shocks everyone that I am still single. Can you advise me of a better method to date now and meet the woman of my dreams?


You say that you have been searching for your young, gorgeous woman to marry “for a few years now.” How is that working out for you? I question that because this pandemic is here for several weeks, yet you have been on the hunt for a few years. With all that you say you have to offer, I agree that is should be shocking that you are still single. Yet, I am not at all surprised. In fact, had you contacted me around the time you started dating, I would have predicted that you might one day find yourself in a quandary.

I have met countless men your age seeking the exact same physical attributes as you. It is O.K. to search for what one wants. With regard to marriage, each person has the right to go after what feels appealing. But if all a person seeks is the exterior while expecting a happily-ever-after, he is in for a shock. In most cases, that person does not achieve the happiness he was hoping for. I am not saying that an older gentleman cannot find and marry a much younger beautiful woman. But when youth and beauty are all there is to a marriage, then the union is nothing more than an optical illusion. Such men are getting the physical outline of a wife, but that is all they can expect to get.

I assume that right now you are in good health, and with Hashem’s help you will remain that way. Nowhere in your letter do you make any mention about finding a woman who is kind and who will be devoted to you. Nowhere in your letter do you mention seeking a woman with whom to spend the rest of your life taking care of each other and enjoying whatever time G-d will bestow upon you. I don’t want to sound like a party-pooper, but a woman who marries a much older gentleman only for his money, trips, gifts, etc., will not be there for him if he ever develops an issue with his health, G-d forbid. What good will her youth and gorgeousness be to him then?

Why did I bring up such a morbid topic to respond to your question? Because you sound like a sensitive man who ultimately would never be satisfied living with a trophy wife who has no heart and soul to go along with her beauty. With all that you have to offer, you still could not find a young gorgeous wife, which is very telling that deep down you crave emotional love, too — and that is what you have not been able to find. As you surely must know, there are plenty of young women seeking exactly what you are bringing to the table. As a matchmaker, I receive frequent requests from women who tell me that they do not care how much older a man might be; if he has money, they will date and marry him. But you know that such a woman would never fulfill you.

I need to touch upon something else that you mentioned regarding men who are encouraged by their rabbis to marry a much younger woman. If a man never had children, then it is true that his rabbi will encourage him to seek a woman who is of childbearing age. And on occasion, men who already have children of both genders will also receive the same psak. I will not state anything that will negate a psak from da’as Torah, except to say that such guidance typically makes the search more challenging, and when these men are unsuccessful in finding such a woman, the rav will, in most cases, issue a new psak to find a wife, regardless of her age, so that the man will not be alone.

Your main concern, though, is that you do not want to hurt a woman if you discover that she is not as attractive in person, which would lead you to end the relationship. That is noble of you. However, do you realize that it works both ways? I agree that an electronic viewing of an individual might camouflage wrinkles and blemishes. But it would be a good idea to be prepared for the possibility that the woman you are communicating with may come to realize when she meets you in person that her vision of you may have been obscured by her phone or computer screen.

When it became clear that social distancing would not be in place for only a brief period, many singles began to panic that their dating life would be placed on hold for an indefinite amount of time. The pain of loneliness and the fear of remaining single became a stark reality to them. To every single man or woman, regardless of age, who reached out to me in the early days of quarantining, I advised that they date electronically. There were those who rejected the notion and stated that they prefer to wait it out for as long as necessary. But most accepted the advice to date via Zoom, Skype, or FaceTime.

A chunk of time has passed since then. Surprisingly, for some of the singles who are in current relationships where they met during COVID-19, the angst that they may have to break up when they meet in person has become very real. In your case, you are concerned about the attraction factor, as are others. Then there are those who are worried that their personalities will ultimately not click when they interact face to face in various settings and discover that they were not a good match after all.

My advice to you is what I tell other singles. I understand that communicating with somebody who is always there for you at the click of a button can create feelings of attachment. Those feelings can activate emotions that oftentimes will give the false sense of having fallen in love. And lately, that is exactly what I am hearing. Singles are saying that they fell in love through the screen. If the man and woman in these “COVID couples” will present to one another in the future as they seem now, then for sure the light of those simchas will wipe away the darkness of the pandemic. However, the reality is that as novel as this virus is to doctors, it is also a novelty to those who are in relationships that began electronically.

Nobody knows the outcome, nor can anybody predict the after effects. It is best to keep your emotions in check. But, even more importantly, I recommend that you have a discussion with any woman you communicate with more than a few times. Tell her that you are concerned for yourself as well as for her that once you meet in person your impression of each other can flip in the other direction.

I will end with this advice. You want to spend the rest of your life with the woman you will marry. She, too, will get older, and, as nature has its way, her looks will age, too. But if the woman you are married to possesses a beautiful heart, then you will forever view her as beautiful as she was the day you met her.

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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