By Baila Sebrow


I became religious in college, and after I graduated, I started dating marriage-minded men. Even though my parents were against it, I always felt attracted to much older men. They are serious and mature, and I get along better with them than the younger guys who act like little boys. Dating went pretty well for me when I had my own apartment. Due to COVID, however, I was laid off from work, and I don’t think I will ever get my job back. I spoke to my parents about my financial situation, and we agreed that I should move back home for the time being.

It was all going well until I introduced my parents to a special man I was seeing for a while, whom I was planning to marry since we had been talking a lot about marriage together. He is quite a bit older and, I admit, closer to my parents’ age. But he is everything I ever wanted in a man: handsome, smart, successful, and very generous with me. My parents hate him, and they told me that as long as I am living under their roof, they forbid me from ever seeing him. He is a total gentleman, and he thinks we should stop seeing each other at least for now, until I move to my own place. That is not going to happen for a long time, and I told him that. We mostly text now, because he figures if we would talk on the phone my parents could hear us, and he doesn’t want to upset them.

A bit more about him. He was never married, and he is dying to have a family, so I feel that we are missing out by wasting all this time. What do people who have always been religious do in such situations? I am asking because all my friends now are religious, too, and they think I shouldn’t date my boyfriend and instead date men my own age. Is this a religious type of thing?


I wish I could say that what you are describing is a mutually satisfying relationship, and that the two of you want to spend the rest of your lives together, and it is only your parents who are opposed to the idea. However, I am not convinced that this is what’s really going on here.

You must own a level of maturity to feel a cerebral connection with a mature man. There is also little doubt that you are broad-minded and not easily swayed by any familial and public opposition.

So here is my take on all this. I have no question as to why your boyfriend was initially keen on dating you, especially as you say he is much older and, in your words, is “dying to have a family.” Your youth, and his certain attraction to you, provided the ultimate green light for him to pursue this relationship. So, regardless of whether one is religious or not, from his angle, choosing you is a no-brainer. Yet, your choice to date him likely comes from a different standpoint.

Most of society assumes that when a younger woman prefers an older gentleman it automatically indicates that she is looking to be taken care of financially. I will agree that in many instances that is completely true. However, as a matchmaker, I have always held on to the belief that even when a woman seeks to date specifically an older man, it is not always just the money that will compel her to marry him. In my matchmaking practice, I have had several cases where women who only wanted to date older men still declined extremely wealthy men because of incompatibilities in particular aspects. Therefore, I am confident that there is always more to a vast age difference in a relationship than what meets the eye.

When relationships of this kind result in marriage, the couple needs to overcome or at least learn how to deal with the stigma of snap judgments and negative stereotypes. So, in answer to your question, this is not a “religious thing,” though I will admit that when such relationships occur, gaining approval from religious communities can be more challenging than in non-religious circles.

In your case, other than your major disagreement about this man, you have had a good relationship with your parents. That said, I feel confident in saying that you established that what would work best for you is a man who demonstrates a higher level of maturity, because that is what you can best relate to.

That is not to say that in the case of your relationship with this man, things are going great. There are many circumstances where family members oppose a dating relationship. Although I am not a fan of going behind anyone’s back, because of the stress involved in keeping secrets, most of the time it is not the man who takes several steps backwards in the relationship, where he not only refuses to see you but will not talk on the phone either. I get what you are saying that you believe he doesn’t want to upset your parents, etcetera, but I am sorry to say that I am not entirely buying what appears to be his excuse.

Prior to COVID, you had this great relationship going on to the point where the discussion of marriage was on the table. The pandemic unfortunately hit, you lost your job, and out of financial necessity you moved back home with your parents. Why didn’t you get engaged around that time? What was the holdup? You did say that you had been seeing him for a while prior to what happened in the world. Not only that, but an older man who never had children and is “dying” to have his own kids should have been on one knee proposing to you. But that’s not what happened.

With regard to your parents, I must say that I understand where they are coming from. I am also inclined to believe that their opposition is coming from a deeper place than mere socially accepted standards about vast age differences.

I will share with you my experience with older men telling me to search for a younger woman for them to date because they want to increase their chances for having babies. If a man is middle-aged, healthy, and accomplished, I do not easily accept what they demand at face value. In most cases—and I expect to receive flak for saying this—men who only date much younger women are looking for youth. And that is also what society has a problem with. It is one thing to look for a particular feature in a relationship for future benefit, but most people do not take it too kindly when they see a man who is with a woman for arm-candy purposes only.

Just so you understand, this is not the first case I have heard of where a much older man is holding off on marrying the woman many years his junior. They may have been searching for a long time in the hopes of meeting her, and when they find such a woman they initially act as though they are eternally grateful. Moreover, they spend much time trying to convince everyone that this is the real deal for them. Meanwhile, weeks pass, months pass, and even years, and nothing even close to an engagement ever happens. Sure, they come up with an excuse when asked, but, in reality, when a person is looking for a reason not to marry somebody, he or she will find it. The tragedy of such a relationship is the outcome. The young woman wasted the best years of her life on empty promises that oftentimes lead to nowhere. Worse is when the man suddenly backs out and leaves her bewildered. Your parents fear for this, and so do I.

My opinion is that if this man is truly serious about you, he would not withdraw from seeing you, and the halt in talking to you over the phone is a clear enough indication that this is trouble. How should he have handled this? If he is a sensitive man, he would stick by your decision to be with him, rather than backpedal to such an extent. I don’t think this is about sparing you from family strife. That he continues a texting relationship just means that he is keeping the lines of communication open with you, perhaps as a way of weaning you off him and whatever you had between each other.

Please excuse my boldness, as I would want nothing more than to advise two people who want to be with each other to go ahead with their plans and run off in the sunset together. But from what you are disclosing, I am sorry to say that I don’t think it is likely to happen.

For your peace of mind, call him directly and tell him that you want to speak to him. When you do, be absolutely straightforward and ask him if he still wants to marry you. Do not accept any wishy-washy answer. It should be a yes or no response. If he replies in the affirmative, then I implore you to not give it more time to happen. You can assure him that your parents will probably come around and that even if they don’t, it should have no impact on what you purportedly share with him. You can also reassure him that as much as it is nice to gain the approval of your family, losing out on love and marriage would be tragic. I will assume that he is religious, so you should further emphasize that halachah does not mandate that one must have parental approval when seeking a spouse. One is permitted to go against the disapproval of one’s parents, provided that he or she is marrying a person who is observant of Torah laws.

If his reason for dating you has a healthy basis, then nothing should hold back an engagement after your conversation with him. If it turns out that he will go along with the original plans to get married, then I advise you to not go around asking for anyone’s opinion. Just inform the people who are important to you about your plans and invite them to your celebration if you wish. Make it very clear that you will not listen to any negative talk about him, since you have made the decision that he will be your husband and the father of your children, G-d willing. Share with him exactly how you intend to handle your relationship going forward if the plans to get married materialize. If he continues to drag his feet, however, cut off the relationship sooner rather than later.

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 Read more of Baila Sebrow’s articles at


Please enter your comment!
Please enter your name here