By Baila Sebrow



When I try to help out friends or family by setting them up on dates, I sometimes encounter a stumbling block due to the age of the women, as the older men hope to have children. If I feel that a 45-year-old woman would be a great fit for a 50-year-old man I know, but he would be reluctant to date her because he wants children, what do I do? Or what about the 36-year-old women being set up with 45-year-old men? What is really the best course of action when only the One Above knows a family’s future?


One of my trademark responses to an older man who unapologetically demands that I find him a young woman who will bear him children is: “I’m a shadchan, not a magician.”

I will assume that you practice shadchanus purely l’sheim mitzvah. If you would charge your clients a hefty fee for searches, you wouldn’t feel bewildered. You would instead be counting your dollar bills for your work. So, I applaud you for your chesed.

Let’s look at this from all perspectives so you can understand what is really going on.

For the men who have never had children, yet desperately long to be a father, our hearts must bleed for their anguish. Just as women have maternal instinct to be mothers, men also have parental instincts. The problem is that men may have been misguided in years past. It used to be that men were told that, unlike women, they don’t have a biological clock. Times have changed, and so has research about men having children. I won’t go into detail here regarding these studies, but suffice it to say that the ages of both partners can determine not just the likelihood for pregnancy but also the health of the child.

For men who have deliberately put off having children, this fairly recent data is a crushing blow. Those who have a close connection to rabbanim are advised to rush to find a young woman who will marry them. Some of these older men have even told me that their rav ordered me to find them a young woman, even if it means that she has young children from a previous marriage and needs financial support. Again, my response is to please tell their rav that I’m not a magician.

We are not living in an era where a destitute younger woman will jump at the opportunity to marry a man regardless of how old he is in exchange for a roof over her head and food for herself and her young children. Women nowadays have more opportunities available to them where education and employment are concerned. Additionally, government and organizational benefits can provide enough so that a woman who qualifies for that assistance does not have to live on the streets and beg for a few coins. Hence, the desperation is not there anymore to compel a young woman to marry a much older man unless she feels an attraction for him. I wish these men and those who have influence over them would acknowledge the facts and instead encourage them to find a partner with whom to share their life.

For the women who are over 40, whether they have children or not, it is incredibly heartbreaking when men in their own age bracket refuse to date them. I blame those who feed them misguided notions. It is a sad state of affairs when there are people who will charge older men exorbitant fees to do a search and all they have to show for it in the end is false hope.

You are absolutely correct that a 45-year-old woman could be a terrific fit for a 50-year-old man. But it’s not just the fact that they want children. I have had many situations where men in their fifties who already have children tell me that they want to date a younger woman because they want more children! Again, they quote their influencers who tell them that this is what they should seek. Quite frankly, I don’t believe that they want more children, simply because in many circumstances, these men can barely support the children they already sired. The truth of the matter is that they just want a younger woman, for no other reason.

You need to understand that just as a doctor cannot save the life of every patient, regardless of heroic efforts, those who are unrealistic about their search for a partner are the clients you cannot do anything for. Moreover, I am sure that you also do not want to hurt the feelings of a younger woman by suggesting a much older man when you know that is not what she is looking for.

Setting up a 36-year-old woman with a 45-year-old man may sound like a good idea to you and others. However, there are also sensitivities amongst women in their mid-thirties who prefer not to date men in their mid-forties. Those who are happily married may not get it. A man is his mid-forties is considered middle-aged no matter how you slice and butter it up. A woman who has never been married and is accomplished in every way sees no reason why she should not be able to date a man closer to her age. It behooves every shadchan to do his or her due diligence in assisting women in their thirties to find the type of man they seek instead of pushing older men on them to date.

It is considered almost like a no-brainer to find shidduchim for the younger 20-something age group. But it gets challenging for those who are committed to helping the older singles. Can it be accomplished? Yes.

The first thing any shadchan needs to do with a client is an intake. You need to conduct an interview with the single man or woman you are trying to assist. You cannot effectively match people you don’t know, even though there are situations where it has happened. You must interview not only your clients, but the person with whom you want to set them up. Look for the hidden messages behind the things they say and keep accurate notes.

Many shadchanim who have been doing matchmaking for years are not as successful as they would hope to be because they become complacent. They might do a search for their client, and perhaps even network a bit, and when nothing turns up, they mentally throw in the towel and move on, leaving the single man or woman behind. Take a tip from the fictional character of Yenta the matchmaker. She left no stone unturned. She made the suggestions and hoped that somebody would accept. She had no shame.

Or even better, take a hint from the old-fashioned “shadchantes” who had a roving eye. Everywhere they went, they saw a possibility for their clients. It could be in your shul or grocery store. Do you have a female client in her thirties looking for a shidduch, and you happen to see a nice young man in that age category and of similar hashkafah in the dairy section of your supermarket? If you are hell-bent on helping your client, start a conversation with him. He might be single and available, or he likely associates with a man who is. It is interesting to note that mothers or other relatives of singles will make that type of effort, but shadchanim rarely do these days.

The successful shadchan does not close shop at 5:00 p.m. He or she sees a possibility in every encounter. I will share with you a story that just happened in one of my shidduch groups that I run. There was a young lady in her thirties who had been on the shidduch scene for a long time. Her profile was presented by a shadchan on the group. A different shadchan happened to be on a Zoom meeting that was starting to feel boring. Wanting to add a little lightness to the meeting, she decided to share the profile of this young lady with the people she was Zooming with. A young man sitting in on that meeting took note of that profile, and although he was a few years younger than the young lady, said that he was interested in meeting her. They met, dated, and recently announced their engagement.

In addition to always being on call, you also need to become an unofficial therapist. No, I’m not telling you to practice quackery. I’m advising you to build a file on every person you interview. Find out a bit of their history to avoid wasting your time and anybody else’s. By keeping a file, you will discover what makes them tick, determine why any previous relationships have failed, and help them avoid the same pitfalls in the future.

Even with all the efforts, the most successful shadchan cannot match every single if the clients do not have realistic goals and expectations. You also cannot change anyone who refuses to adjust their ways or fixed viewpoints that clearly do not make sense for their standard of living. Sensitivity to every client while encouraging them to open their hearts and minds is important. Moreover, listening, and also hearing what they say, as well as being cognizant that it is not about you but them is paramount to successfully matching a client. At the end of the day, after you have done your hishtadlus in shadchanus, yes, it is up to Hashem as to who will marry which person, and who will have children, whether at age 20 or 50. The wonders of Hashem never cease to amaze!

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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