By Baila Sebrow


I started going out with a divorced man who is much older than me. Everyone warns me that he is not serious and that in the end he will hurt me. He has a bad reputation, and I actually spoke to him about it. He said that there is a lot of exaggeration about him, but he admitted that most of the things I heard about him are true and that he did hurt women in different ways. Now, he wants to settle down and get married. He is willing to let me meet his therapist who in the past advised him to break up with the women he dated. The therapist feels that he has done a lot of work on himself and that he is now ready to really get serious with somebody.

I was never married and I’m not meeting anyone interesting. I feel like I could take the chance with him because he is lonely. I know that he is crazy about me and he told me that he loves me right after the second date. He treats me like a princess. It’s like he idolizes me. He told me that he has never felt this way about anyone else. He also told me that I should daven for us that things should work out. Isn’t that a sign that he is trying to be serious about us?

Everyone is begging me to stay away from him, but I fell in love with him, and I can’t break up with him. He is so exciting! Isn’t a Jew supposed to give everyone the chance to be a good person? What do you think? Is it possible that I brought out something different in him?


No, I don’t think you brought out anything different in him. Rather, you have demonstrated empathy and vulnerability, in the same way that I am sure other women have in the past. And from what you are telling me about his history, people with his track record tend to have a heightened sense in picking up the characteristics of an empathetic and vulnerable person. Those characteristics draw them to such a person in the first place. Besides, they would never be successful with an unkind type of personality. In an effort to gain the affection of the woman they are interested in, they know that they need to prove their sincerity, so they will say and do whatever they need to that end.

As such, it’s no surprise that he treats you like a princess and acts in ways that make you feel idolized by him. Maybe he has even convinced himself that this time it will be different. That is why he is asking you to daven for the relationship to work out. It could be that a part of him may want to have a successful relationship; after all, he is lonely, as you say. But what happens in such cases is that the empathetic and vulnerable person falls victim in the end.

If you think I might be wrong about it, do your own research. Find out about the women this man dated before you. What was their life story before he came into their lives? I am sure you will discover that the women who established any relationship with him had all the makings of a sensitive, soothing, understanding type of person. And most likely they were vulnerable, too. Perhaps they were coming out of a divorce or some demoralizing or even traumatic situation, and a little attention from a man who knows how to say the right things reeled them him.

He said that he loves you after the second date. Did you seriously buy into that? Think about it: the man is experienced around women, he barely knows you, and he fell in love with you? That is not just a little red flag popping up; he is practically waving the red flag in your face.

What does he mean when he admitted that he hurt women? How did he hurt them? Did he date women leading them to believe he will marry them, only to abruptly end things? That is no light matter and bad in and of itself. But was there something more serious that happened in his relationships? What has he shared with his therapist? If he admitted the truth of what happened in his previous relationships during his therapy sessions, then why is he saying that his therapist advised him to break up with the women? Something does not add up accurately. So let’s take this apart with the little information you shared.

While all therapists hope that their patients will be honest with them, there are people who are so disturbed that they purposely lie to the person to whom they are turning for help. It may make no sense, but patients have been known to be manipulative and twist facts so that the advice will benefit the type of life they feel comfortable living. It could be that this man omitted or misrepresented truths to his therapist so that he can continue living the life he knows. He may not be happy living a lonely life, but maybe, deep down, that is his comfort zone.

If he was honest with his therapist, it’s possible that the therapist’s advice to break things off might have had more to do with him than the women he dated. Perhaps the therapist felt that he is not emotionally stable enough to be married. Maybe he shared how he had hurt the women he dated, as his reputation precedes him, and the recommendation to break up with the women was to protect them from him!

You mention that you have not met anyone as interesting as this man, and that is quite understandable. Having dated so extensively, he must have a wide social circle, and he probably attended many varied events and visited numerous locales. He certainly has what to talk about, unlike a man who lives a quiet life. With him you will certainly get plenty of excitement. The risk you are taking is that he will keep you on a high pedestal, but if he pushes you, so to speak, you stand the chance of falling from that high place, G-d forbid. The bigger the drop, the greater the chance for injury.

So, where do you go from here? It sounds like you have an open line of communication with him, and that you feel comfortable talking to him about what’s on your mind. In most other relationship circumstances, I would say that as long as you have that between both of you, it’s an all-systems-go situation. However, I can’t say that in this case. Your “open” line of communication with him may not be sincere. He will answer all your questions and put your mind at ease, but you will never know how truthful he is really being with you.

You say that he is much older than you, and that tells me that he is not likely to change anytime soon. That is something you will need to accept. I understand that his therapist feels that he has done the work and is ready to live a productive life. But what if something triggers him? A while ago, I had a situation where a young lady reached out to me about the man she was dating seriously. This man had a specific issue that he was in therapy for. The man wanted to marry her, and the therapist assured him that he was fit to be married.

The young lady was understandably concerned and although she had many conversations with his therapist, she still felt uneasy. So when she reached out to me, I advised her to ask his therapist the following question: Is it possible that he may get triggered, and fall off the bandwagon, consequently going back to his old ways? She called me back to report that the therapist responded to her that, yes, that is a possibility. My question was then directed to the young lady, and I asked her, “Will you be able to live with that?”

Using that chain of logic, I will advise you take him up on the offer and speak to the therapist. Make sure that everything is clarified to you, and that you have a full understanding of whatever his issues may be. As soon as you hear that his therapist has given him the go-ahead, be direct and ask him or her if there is the possibility that he may do to you what he has done to others. I would venture to say that in all probability the answer will be yes. At that point, you will have to ask yourself if it’s worth taking such a risk.

If your answer is yes, here is what I recommend. It is not clear to me how far along you are in the relationship. I don’t want you to have any regrets, so I will tell you that if you are able to keep a clear head and not let yourself get caught up in any head-over-heels emotions, continue to see him while keeping your head above water. Make sure that he is aware that you are being cautious specifically because of what you know about him.

The Torah tells us to be forgiving, to be dan l’kaf z’chus, and to give everyone the opportunity to do teshuvah. However, when it comes to a shidduch, one has to be extra scrupulous in making sure that the person he or she is choosing to marry is somebody who is G-d-fearing, has a lev tov, and is mindful of how he or she treats other people. If at any point you become aware of bad traits in that person, you are within all rights to break it off.

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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