By Baila Sebrow

By Baila Sebrow 


I’ve been divorced for a little over three years, and I have four sons, ages 15, 13, 10, and 6. Even though I’m only 37, the only men who ever wanted to date me for marriage are the ones who were closer to 60. The men my age all turned out to be players; after wasting my time dating me, they said they can’t take on being a father to four boys. Like they didn’t know I have four boys before we dated?

My life as a divorced woman is hell. It’s not just the loneliness. My ex has no interest in our boys, and when Shabbos comes, they never go to shul. It hurts the most on Friday night, when my boys see the men walking on the streets with their sons. I tell my big ones to go to shul, but they say it’s weird because they don’t have a father to go with. When I visit my parents, they go with their grandfather, but at home, they won’t go. I live on a frum block, and not one neighbor has ever offered to take at least one of my boys to shul. They daven at home and we eat alone. But that’s not why I am writing to you. I just want you to understand where I am coming from.

I decided to throw in the towel and agreed to go out with a man who is 64. He turned out to be wonderful to my boys, and he is also wonderful to me. He takes care of us financially and is very caring about everything else. He wants to marry me, but I admit his age does bother me, and everyone I know is against this shidduch. Our shadchan told me that in a few years even a guy who’s 64 won’t want me; she knows tons of women in their forties and only men in their seventies will date them. If he is my only chance, I don’t want to lose him. He does not look his age, and he is in perfect health, bli ayin ha’ra. Our shadchan also reads your column, and I told her that I am writing to you. What is your opinion?


I have many opinions about your letter, and though your purpose for writing to me was not about your life as a divorced woman, I cannot allow the pain caused by the way you are being treated slide by unaddressed. Your plight hits home because it is shared by many other single men and women who are either disregarded or inadvertently overlooked by married folks with their own families or busy lifestyles. Married people rush to get ready for Shabbos, with the men heading to shul, their sons in tow, and come home to enjoy meals with their family, yet have no clue that nearby there are others not as lucky as they are. The married women are busy with their meal preparations while taking care of the needs of family members, and though they may invite other married couples to join them for a Shabbos meal, more often than not they leave those who are single to eat alone. This is an ongoing issue, and I have spoken out against this appalling situation on various media platforms.

When singles who are in such a predicament reach out to me for advice, I typically encourage them to organize meals with other singles so no one is alone, and with regard to boys who have no father taking them to shul, I suggest arranging something with the single dads from the community. Only those who are in a particular matzav can fully comprehend the anguish of another, and so the singles need to establish a society of kinship within their community where they each take care of one another.

You chose to date a man 27 years your senior just to improve your situation. That is what I have an issue with. Let’s talk about the dating scene for divorced women in your age bracket with more than one or two children. According to the calculations you related, you were 34 years old when you got divorced, and I imagine that the men within your age range were not mentally and financially willing to take on the responsibility of becoming a full-time father to children not biologically their own. Shame on them for wasting your time and playing with your emotions. To get you out of the bind you are in, your shadchan introduced you to man who no doubt asked to be set up with a much younger woman. I take huge issue with your shadchan for doing that. Of course, given the choice to date a much younger woman, most older men will choose her. Any shadchan who will first introduce a 37-year-old woman to a 64-year-old man before suggesting a woman his own age is being unethical to her middle-aged clients. It’s no wonder that women in their fifties and sixties cannot find men their own age to marry them! And to tell you that in a few years, all you will be able to get is a man in his seventies? Your shadchan should feel her cheeks burning from shame for talking that way. This shadchan figured that your predicament makes you ripe for the picking of a man many years your senior who is ready to put a ring on your finger.

I will say that in most cases, women as young as you refuse to date much older men, but based on what you are telling me—that he takes care of you and your children financially—in such a case, the shidduch will take off.

If you were to tell me that you are compatible with this man in a way that makes you feel happy and safe and that you share similar goals of family life, I would advise you that age is just a number, so ignore the naysayers and marry him. But you are not convincing me that this man is the one you believe is your bashert. Rather, you are giving me all indications that this is just a marriage of convenience for you, and probably for him, too, but for a very different reason. Here is something to consider: Would he want to marry you if you were around his age?

Am I telling you to break up with him? No. I am telling you to hold off on marrying him until you are certain that you would still consider marrying him were your life not as unpleasant as you describe it. Take the time to get to know who he is. In fact, even if he had been within your age category, I would still caution you to do the same. It is never a good idea for anyone to jump into a marriage while going through a crisis. Marriage is not meant to be the solution to a problem, unless the person you are marrying is compatible with you on other levels, too. Moreover, stress is known to change how someone makes decisions. At that stressful stage, the focus is on removing the wrong and making right whatever is causing you stress or troubles. For example, your boys have no one to take them to shul, and you are alone and lonely without financial backing. Along comes this man, and, voilà, those problems are automatically solved. Ask yourself: If those negative factors were not an issue in your life now, would you have ever contemplated him as a marriage prospect? If the answer is no, that should tell you all you need to know. However, if after pondering your situation you come back with the answer that maybe you would not have initially considered him, but he is in fact a gem of a man and you accept his flaws as well as his qualities, then, yes, go right ahead with your plans, after giving yourself enough time to get to know him.

If you indeed plan to marry him, there are some points to bear in mind. You will have to expect lots of criticism from people from both sides, yours and his. That could place tremendous stress on your relationship, and, at times, may even cause you to second-guess your choice. Consider the notion that your significant age gap will also mean that your hobbies and interests will likely be dissimilar. Though that could happen in any type of marriage, how you both deal with it in a 27-year age difference will have major impact on the relationship going forward. There will undoubtedly be other issues arising that are of natural consequence, and being that you are younger, you may find yourself feeling bewildered. 

In addition to getting to know him and his intentions well, I advise you to do two things. Please retain a couples’ therapist who can view your relationship from a professional perspective, which is very different than the opinions of those who are against this shidduch for the age factor alone. Additionally, reach out to a rav for guidance, not just about your personal challenges, but also to steer you toward an effective decision-making process in various areas of your life. 

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 Baila also hosts The Definitive Rap podcast for and Israel News Talk Radio. Questions and comments for the Dating Forum can be submitted to Read more of Baila Sebrow’s articles at



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