By Baila Sebrow


I’m really a good person, but when you hear my story I know you will think that I’m horrible. A few years ago I dated a man for a short time, and I really liked him. He broke it off not too long after we started going out. I didn’t care that much at the time because that’s his M.O., and everyone knows it.

My dating life has been one disaster after another. Then I heard through the grapevine that he was dating someone seriously, and I actually saw them together once. Because I was in a bad place, I got very angry and jealous, and I decided that I wanted him back. So I started texting him, and one thing led to another, and he came up with some excuse to tell the lady he was dating that he is breaking up with her. We started dating right away, and we have been dating ever since.

Now he wants us to get engaged. I am so torn because I’m not sure about my feelings for him. Also, what if he does to me what he did to the woman he dated before me? I would feel terrible if he went back to the one he dated and left for me. What do singles usually do in such a case? I want to add that he is a gentleman and treats me very generously.


Wow. I typically keep personal feelings out of my responses. But in this case, I must express my sentiments for the one person you barely give mention to. The sole victim in this tale of woe is the woman your heartthrob carelessly tossed aside for you. And it sounds like he might be forced to ingest a hefty dose of his own medicine!

I would love to admonish you for your hand in this saga. But I believe that deep down you are a good person, as you have said, yet misguided. So let’s go with that so you can understand what you have done and why, and to help you to recognize what Mr. Lady’s Man is really all about.

From what I understand, you dated this man no more than a handful of times. Although no one enjoys being rejected, you dealt well with it, specifically because you were aware that you were one amongst many others this man has treated in such a way. And life went on. Unfortunately, you did not experience success in finding someone else to share your life with, so when you heard (and saw) that another woman might be having some luck with the very person no one else has been able to get to commit, it sent a jealous, angry bolt through your system. Your reactive feelings were completely normal. You must’ve been wondering what she has that you don’t. But in an ethical world, that should have meant for you to stay as far away from him as possible. Yet you took matters into your own hands and treaded where very few would dare. You made a major play for a spoken-for man. That was unfair and unscrupulous.

One can say that if he had been happy with the woman he was seriously involved with, he never would have jumped ship so quickly. But that would be speculation. I don’t know what you said or did to convince him, nor do I know if it was a weak or defenseless moment for him when he initially responded to your advances.

You were having a difficult time with shidduchim, and the fact that he was already involved with someone likely made him appear more attractive to you. There are many people who will tell you that when they were unattached, other singles never gave them a second glance, but as soon as they got into a relationship, all of a sudden they were on everyone’s wish list. One of the reasons might be that when they are off the market, they are more at ease with themselves and therefore make a much better impression on others. Another cause might be that since another person wants to marry this person, that makes him appear more sought-after.

This is reminiscent of stories about houses for sale that sit on the market for a long time. As soon as it becomes known that someone made an offer to buy that house, people who have viewed the house previously and had no interest in it will often jump into action to make an even higher offer to outbid any others. It is human nature to want what someone else has. And it takes integrity to stay away from what does not belong to you and what someone else has already laid claim to. When dealing with issues in shidduchim, breaking up couples is serious business, not something anyone should ever dare play with.

I am not trying to verbally beat you up about what you have done, nor do I want to make you feel bad about yourself. But just so that you can learn how to deal with your current dilemma with regard to getting engaged to this man or ending the relationship, you must first come to terms with all aspects leading up to this point.

I can imagine that one of your concerns is whether you can trust him. Based on your personal experience with this man, I am sure you will agree that he is impressionable when it comes to women. Would he do to you exactly what he had done to her? I don’t know the man, so I can’t say for sure either way, but, typically, those who betray once are susceptible to doing it again. And even if by some chance you manage to hold on to him, you will probably always worry that you may lose him to someone else. Once someone cheats, history tends to repeat itself. In most cases that has been proven to be true. However, since each person is an individual, and each case is different, at the end of the day everyone deserves a fair chance. However, his past indicates that he is not likely to remain in a situation he is unhappy about. That in itself does not make him bad, but he demonstrates a tendency to leave a relationship rather than work on it.

Let’s put trust aside for a bit and go on to another concern. You are worried that your feelings for him may not be genuine. And that is a strong possibility. There are times when people date, break up, and reconcile. But the reconciliation is usually based on a healthy foundation. People who decide they want to try again do so because they either came to the realization that the grass is not greener on the other side or that they shouldn’t have broken up in the first place. You were so eager to take him away from the other woman that in all probability you didn’t even stop to figure out how you really feel about him. And when you started dating again, he may not have made such a great impression that your feelings would grow enough to want to get engaged. That might be your subconscious recognizing defects in his character.

So let’s bring it all together. How does a person go from a serious relationship with someone to just ending it for another? A serious relationship, even if it’s not marriage, is still a commitment of sorts between two people. For this man to be able to do that so easily tells of a person so driven by his own needs that he does not stop to think that he might not be acting honorably.

In discussing what causes people to be so driven that they neglect to stop and think about the consequences of their actions and the hurt inflicted, it goes back to the issue of trust. Those who break trust are typically driven by their own needs. Their overwhelming need to satisfy their desires oftentimes clouds their ethical vision, and they have difficulty discerning between doing right by others or wronging them.

Your concerns are valid. It is normal for you to feel that if he deceived one woman, it would not be too difficult for him to do that to you should another woman come along—or maybe he would even go after the woman he left for you! And sadly, that could happen even after many years of marriage. It is interesting, though, that you now consider what he did to that woman for your benefit as a stain on his appeal.

The excitement of being involved with someone you cannot have has finally worn off. He is all yours now. You can get engaged to him, marry him, and never look back at how it all came to be. But you can’t. Because to you, he is no longer just a guy you once dated and in whom you had no real interest so you didn’t care when it ended. You are now looking at him as a cheater. You have no respect for him. And without respect, a relationship disintegrates very quickly.

The thrill of the chase is over for you, and it appears that you might be looking for a way out of this relationship. You are conveying that by the questions in your letter. It is also transparent that you do not trust this man. Trust is the major groundwork in a relationship. I believe that the set of circumstances in which you were brought together as a couple is exactly what is now pulling you apart.

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


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