By Baila Sebrow


I had a strange experience recently that has left me sad and conflicted. I am a 40-year-old divorced woman with a child. I generally date men in the 40s-50s age range who are similar to me — educated and professional. I have found that most mature couples can work out hashkafic differences, so while I consider myself Orthodox, I have dated men who are modern Orthodox and also those who are very yeshivish.

I met a lovely man at a frum singles event and we began to date. He is smart, successful, funny, and warm. He is divorced after a brief unsuccessful marriage, and he does not have children. He generally treated me very well, showed and expressed concern and feelings for me, and wanted to move toward engagement. We began premarital counseling with a therapist who knows each of us separately for several years.

This gentleman acknowledged that he is more modern than I am but is willing to move toward my way. Other than wearing a different kippah, and other nuanced lifestyle choices, it wasn’t clear to me what he meant. After a few months of dating, he admitted that he stopped keeping Shabbos about three years ago because he was so lonely. He assured me that he would resume doing so as soon as we got engaged. He promised me that kashrus and taharas ha’mishpachah would be upheld, and if we had kids they would go to a right-wing yeshiva of my choice.

I feel very conflicted. He is very kind to me and would be very giving to me and my daughter both emotionally and financially. However, I feel that he misled me regarding his observance, as did the therapist we were seeing. The therapist kept discussing nuances — for example, a white shirt versus colored shirt on Shabbos, and didn’t mention that he is mechallel Shabbos. The (very frum) therapist claims he thought I knew, and in any case lots of older singles become lax with Shabbos and other areas and resume observance with marriage.

I was not satisfied with the therapist’s explanation and asked the man I was dating to meet my rav. He agreed, and he went and liked him very much. However, the rav was very concerned both about this guy’s lack of observance and that a man in his fifties spent most of his life single with no kids. My rav said that he presented as self-absorbed to him.

I experienced that once or twice, but I know that when I call him out on it, he comes around. For example, we met in the city for a date because it was more convenient for each of us work-wise. I lost a contact lens, and I had to explain to him that he needed to drive me home. In my experience, he is usually very thoughtful but occasionally needs direct prompting.

After two weeks of going in circles around the observance issue, where he said “once we get engaged” and I said “I need to see it and trust it to consider continuing,” I broke up with him. I told him that this was making me very anxious and I need a break. He told me he would start keeping Shabbos immediately if it is that important to me, that this relationship means too much to him. I told him that his observance is his own, and I need a break.

It’s been a week since I broke up with him, and I am second-guessing myself and missing him terribly. Please advise.


When couples who date seriously break up, one or both do so impulsively in the heat of an argument, or after much soul-searching and internal deliberation. It is not uncommon to second-guess oneself after a breakup. You were used to having someone in your life, and his presence and familiarity was comforting to you regardless of any conflicts. It is my understanding that your reason for breaking up had nothing to do with impulsivity. On the contrary, you discussed your issues not only with each other, but you brought a therapist and your rav to facilitate any negotiations in order to make this relationship work.

Because you want to make sure that you didn’t make any mistake, it is important to rehash the relationship after the fact from your perspective. Let’s examine the circumstances. But remember that the only information I have to go by is the bit that you shared in regard to your communications with him, as well as communications where the therapist and rav are concerned.

The myth that needs to be debunked is the thought process that mature adults can work out their hashkafic differences. On the contrary, it is the young couples who oftentimes stand the best chance of working out any differences, should they feel inclined to do so. The reason is very simple; they only have each other to worry about. When mature people have children from previous marriages, and they are blending families together, being on a different page where hashkafah is concerned becomes more of a challenge. Not only that, but the more mature a person is, the longer he or she has been used to living a specific lifestyle. Three years of not keeping Shabbos is a long time. So, in essence, what you see is what you should expect to get, regardless of any promises the man pledges for the future.

But we are not just talking about what type of schools you will send your children to or the type of yarmulke he wears. And while it is great that you have no disagreements where kashrus and taharas ha’mishpachah are concerned, your issue with him is that he does not keep Shabbos. That is not a simple hashkafic difference. A person who does not keep Shabbos is violating a religious commandment. The man is not frum.

I get that he is lonely. And I will agree that, sadly, there are cases of divorced people who give up on religion for various reasons, but that does not change the fact that he is not shomer Shabbos. If he is complacent with this sort of lifestyle, what makes you think that he will uphold his promise to keep Shabbos when he gets engaged? Going further, what would he do if after the wedding things don’t work out, G-d forbid, and he has a serious argument with you? Will he then be mechallel Shabbos because he is upset or feels lonely again?

I am not sure why the therapist did not disclose this information to you, unless the man you are dating asked him not to tell you, and he was professionally bound to uphold patient confidentiality. Or, perhaps based on discussions with both of you, he truly believed that you were aware of all the facts. I am concerned, though, that the therapist defended this man’s lack of observance and instead focused on the silliness of colored shirts vs. white shirts on Shabbos. Then again, was that also a topic of discussion that you might have had differences about?

Why did your rav feel that he is self-absorbed? The fact that he’s in his fifties with no children is not enough reason to assume that about him. There are many childless people in the world, married or single, but to say that because they were not blessed to have children is a sign that they are self-absorbed is absurd. Perhaps this man demonstrated other mannerisms and, combined with his chillul Shabbos, the rav came to that conclusion. You do mention that you have called this gentleman out on it once or twice, so maybe there is a bit of that there. However, it’s a positive sign of gallant behavior and willingness to please you that he quickly complied with your needs.

It could be that your dismay with this man might stem from your resentment towards the therapist. You feel betrayed by the therapist, and along with your rav’s opinion, that sent you running for the hills. But you now miss the person in your life you were talking about marrying. And you miss him also because you realize that he was good to you and your daughter. That is no small matter. Many problems in second-time-around relationships stem from a child not getting along with a potential stepparent.

Putting the specific therapist and rav aside, while dating this man you felt compelled to reach out to professionals as third parties. Why? Although it is not a bad idea to seek premarital counseling, the fact is that most couples only do so when there are conflicts. So, even though he did not disclose his lack of religious observance, regardless of how well he treated you and how well you both got along, there must have been something bothering you and possibly him, too. That is the area that you need to delve into.

From the way you are describing the relationship you have with this man, it sounds like he cares about you and has deep feelings for you. It would be a good idea to contact him and have a heart-to-heart conversation, minus any third parties. You need to speak directly to one another without any facilitators. You come across as an articulate woman, and you should have no problem speaking to him directly.

Start by expressing that perhaps you may have been a bit hasty, and that you would like to see if there is a way to salvage the relationship. Tell him everything that bothers you—from his concealing that he is not shomer Shabbos to anything else that is on your mind. Hear him out, and if you feel that he is being sincere, take it one step further. Tell him that if he is serious about observing Shabbos it will not work if he does so only to keep you in his life. He needs to commit to that lifestyle whether you marry him or not. If he tells you the same story that he will do it after you get engaged, or if it means that much to you he will do it immediately, tell him that is not good enough. At that point, you will have the reassurance and acceptance of closure that it cannot work out between the two of you. However, if he is earnest about living a Torah-observant lifestyle, and he’s receptive to encouragement and motivation, then it is possible that he will be a sincere chozer b’teshuvah.

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 here.


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