By Baila Sebrow


I’m writing about a guy who broke my heart because of how he treated my daughter. She was engaged to him, and one day he just ended it with her; nobody knew why. He sent someone to pick up the ring after he told her, and that was all. This happened when she was 19. Now she’s 23, and the guy is 30 and divorced. She hasn’t gotten married because she couldn’t get over him, and now he wants her back.

In the meantime, a few months ago, she started going out with a different guy, who is 35 years old. There are things about him that bother her, but I don’t think it’s so bad. For example, when he wants a table for two in a busy restaurant, he makes a reservation for three, and when they are seated he says that the third person canceled. The first time he did that, he explained that he hates small tables and that it’s the only way a restaurant will give them a bigger table. My daughter doesn’t like when he does that.

Also, she says that he’s always straightening things on the table, and he needs things to be just as he wants it. He is demanding to waiters and waitresses, and when he gets the bill, he tells her that he will tip well, but she knows that’s not true.

Her other complaint about him — and this is ridiculous already — is that he doesn’t want to talk on the phone with her anymore, though he did in the beginning. He just wants to text, even to make arrangements for the next date. But they text day and night. That’s not enough? You can’t have everything when you want to get married. This is how guys are, and I wish she could understand that.

The problem is that she wants the first guy back, and I want her to marry this one because the shadchan swears by him. I trust this shadchan because she made many shidduchim. Who is right?


I think both guys might have to be let go!

You stated regarding this new guy that the shadchan “swears by him.” He must be quite the charmer that he won her over in such a big way. But here is where I’m baffled. How can any human being “swear by” another human being? I don’t care how well a shadchan thinks he or she knows a client; the reality of such situations is that most people will show only the best side of themselves to the person they hope will get them what they want.

Even if the shadchan invited this man to her home and spent time with him, the way he conducts himself on dates and in relationships can be vastly different than in other social settings. So, with the greatest respect to this shadchan, and for the benefit of your daughter, it is best that we leave the shadchan’s strong endorsements of the man out of the equation and instead focus exclusively on his actions.

The man your daughter is dating knows exactly what he is doing with regard to the way he is handling the relationship with her. However, he is slipping up in other areas that he does not seem to have control over. There are so many red flags in the little bit you are telling me about him that I have no doubt there are even more alarming aspects to his personality that your daughter either has not shared with you or may still be unaware of.

Let’s start with his insistence on texting as the only mode of communication, as opposed to talking on the phone. If this would have been his M.O. from the beginning of their relationship, I would say that it’s probably a habit he picked up. But since this is a fairly new development, I am inclined to believe that there is something else going on his life when he is not with her. It may not necessarily be anything unfavorable, but it does leave room for speculation.

The advantage of texting somebody instead of speaking to them on the phone is that you can be anywhere and with anyone and still communicate. Phone calls, on the other hand, are a bit trickier, for obvious reasons. In the early stages of your daughter’s relationship with this man, they spoke on the phone, and as it progressed, he no longer does. That tells me he is likely preoccupied with something he is not comfortable sharing with her. It might be innocent or even work-related. But it is not standard behavior for a dating couple.

I can understand that people might feel uncomfortable at a table designated for two patrons in a restaurant. Those tables are typically small. I agree it can feel crowded, and perhaps even claustrophobic to some, if there are many dishes ordered and brought to the table. But to always make a reservation for three people when there will only be two is distastefully dishonest. Worse still, he sees nothing wrong with it! On the contrary, he finds fault with the restaurant for providing such a table. Sadly, that is common among people who act wrongfully. They justify their actions to make it seem that they are the ones being wronged. You might think this is farfetched, but such personalities commonly take these attitudes home and treat their family in the same manner.

What do you mean when you say that he moves things around on the table? Is he not happy with the way his cutlery and napkin are placed? Or does he perhaps dislike where the salt and pepper shakers are positioned? What else does he complain about? I’m sure it doesn’t stop there. After all, according to what your daughter says, he is not exactly sweet to the wait staff either. Based on what you are saying, I think it is a good idea that this man doesn’t call her. It would be even better if he would also stop texting her. He appears to be a demanding and difficult character, and she should not waste any more time with him, especially since she is not happy being with him anyway.

What happened with the man she was once engaged to? From the little bit you disclosed, your daughter was engaged to him, and, out of the blue, without warning, he ended their engagement. Here is my problem with such scenarios. The rejected person feels like the decision came out of left field, particularly when everything seemed to be going fine. But, even more awful, the person feels as though they never received closure. Without closure, there can never be healing.

Picture an open wound. Until it is stitched closed or closes by itself, it will be gaping and prone to bleeding and infection. The same happens in relationships. He broke up with her, but I am certain that, from his perspective, he had time to make peace with his decision. By the time he ended it with your daughter, he had all the closure he needed. He was good to go and got married to somebody else. But your daughter wasn’t, because she was never offered closure. So not only was your daughter surely devastated, but I fully understand why you felt heartbroken, too. You were in pain for your child.

This guy married somebody else, while your daughter couldn’t move on. Things didn’t work out for him in his marriage, so he felt ready to make a second go with the young lady he was once engaged to. That she wants him back is no surprise; she has been pining for him all these years. In her head, she likely idealized him, and when he came for her after his divorce it must have felt like a dream come true for her. But why should she trust him? Why should anybody believe that he won’t pull the same tactic on her again?

People do get back together after breaking up. But such reconciliations can only be successful if the breakup was orchestrated and carried out in a humane manner. This man did not do that. An engagement is not like a dating relationship. The ring represented a promissory object of significance that they would be sharing a life together. Swiftly ending it and impersonally taking the ring back by messenger are not the actions of a gentleman.

Your daughter desperately needs closure in order to move ahead. If she wants to see that man she was once engaged to, then let her meet him — but not alone. You or someone she trusts and who has knowledge of their history should be there with her. He needs to explain in detail why he did what he did to her. You can expect him to say the usual line in this type of circumstance — that he is a changed man and that he realizes that he gave up a good woman. Those are the typical scripts that are recited. And that is why she should not be alone when she hears him say that. He needs to be compelled to explain himself and offer a sincere apology.

In my opinion, she should not take him back after what he did to her, only because she risks that he may do it again. But the reality is that she will probably follow her heart. Whatever she decides, do not fight her on it, as it will only cause her to want him more. Support her decision and be a sounding board for her regardless of how the situation plays out.

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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