By Baila Sebrow



I know that this is going to sound childish, and I’m embarrassed to tell you the whole story, but I really need advice. After my divorce, I was in a bad place emotionally. I could no longer be friends with the people my ex and I hung out with, because they were his friends first, so I needed to find new friends. It’s embarrassing to say that the people I got involved with were not good people. These divorced friends were big bullies. But because they were nice to me and they accepted me, I clung to them even though they weren’t nice in general and there were bad rumors about them. That ended up ruining my reputation, too. But all that happened a long time ago.

Since then, I’ve changed a lot, and that group is not the same anymore. Some of the people got married, and some moved away. One of the guys in that group is somebody I had a huge crush on, and at the time he was dating a nice woman I knew; I think he might have even been engaged to her. But since she was not part of the group, my friends and I convinced him to break up with her so I could have him. It always bothered me that I did that.

Now that most of us straightened out our lives, he called me and asked me out. We started dating, and it looks like it’s getting serious. But in the back of my mind, I’m worried that something will go wrong and he will leave me for someone else. He was known to do that a lot.


I think what you are basically asking me is if a leopard can ever change its spots. The answer is no. People are who they are. They can repent if they did wrong and they can behave better in the future. People can also work on themselves and fight their nature. However, trigger them or push them into a stressful situation, and their old self will typically peek through. If you are lucky, it will not be to the extent of their past ways, but it will come into focus in some form.

When you get into a serious relationship with somebody who you know has done things that are morally wrong, you need to accept who they were and respect them for the way they are now, but don’t be surprised if a part of their past behavior may reveal itself. That is the reality of humanity.

If you had led a saintly type of lifestyle when you knew him back then, I would discourage you from building a serious relationship with this guy. Not because I don’t believe in teshuvah — I very much believe that a person has the ability to improve himself, and thus his past should not be held against him. But when it comes to choosing a life partner, there are other factors to consider that could have a major impact on your life and future.

In this case, you are both coming from a similar situation. You were divorced and, for whatever reasons each of you had, you joined a bad group of friends and you did things that were not nice in order to fit in. But at least you knew that it was wrong, though at the time felt you had no other social outlet that would accept you. You express regret, but what about him? Has he really changed, or is it just that the group dwindled and you assume that he’s a better person now because of it?

It is noteworthy that you now see yourself as a potential victim at the hands of a person you once partnered with. Is it also possible that deep down you may not want him as much as you did previously? There is a remarkable phenomenon that when singles are in a dating relationship, not only do they receive more attention from the opposite gender, but there are those who will become fascinated with that person though they wouldn’t have given that person a second glance prior to his or her new dating status. Those who lack scruples might try to break them up. The strength of the relationship will determine whether the relationship will survive.

In your case, you had a huge crush on him but made no proactive move to get him to ask you out after he broke up with that woman. You did nothing to get more of his attention after you were responsible for his breakup.

Why are you feeling so uncertain? You got what you wanted! He’s no longer that attractive to you anymore? In many cases, when people are in a serious relationship or engaged, they are more at ease with themselves and make a better impression on those around them. Other times, the fact that somebody else saw something in them can foster stronger interest that perhaps they inadvertently overlooked before. Like the dress or suit nobody wants to buy until they see another person trying it on, or the club nobody wants to belong to, until somebody else joins—those are examples of things that become attractive as soon as another person finds it charming.

Please understand that my motive for explaining the mindset of going after somebody who is taken is not to make you feel bad, but to encourage you to do some soul-searching. Try to determine why you did what you did, if that crush you talk about was real, and if whatever you are sharing with this guy has any value.

I can respect that you are wondering whether you can trust him. After all, this is a man who allowed himself to be so easily swayed that he broke a trust — and from what you say, he is notorious for doing so. Who is to say that it will not happen again? No one can honestly promise you that; probably even he cannot.

I do not know the circumstances of the relationship he had with the woman you think he was engaged to, and you did not share how you went about your scheme to break them up. It is possible that the relationship was on shaky ground to start with and that they would have split up regardless. Maybe they were having problems that would have worked themselves out.

So what happened to make them break up? Was he lured to cheat on that woman? Is cheating what you are afraid of? Or does he just easily lose interest and quickly moves on to somebody else? Since you are not disclosing comprehensive details, I will cover as much as possible to help you in your dilemma.

There is an old adage: “Once a cheater, always a cheater.” If we are dan l’kaf z’chus that a person did teshuvah and therefore is to be treated as being pure as a newborn, then, OK, take your chances. However, I know that you were not looking for that answer from me. The reality of life and what mental-health professionals will tell you is that the likelihood that it will happen again is very strong.

Regarding men who are notorious for losing interest in the women with whom they are in relationships, the same assessment holds true. There are men whose goal is to get the woman they want. Once that objective is met, they lose interest because they had no other goal, such as nurturing a relationship. So they either look for the slightest excuse to move on, or they will just leave, oftentimes citing some nonsensical reason. If this keeps happening over and over in his relationships, and if that is what happened in his previous marriage, then you have good cause to feel apprehension.

The bottom line is, can you trust this guy? People who can easily break a trust are the type of people who are driven by their own needs. They have little empathy for those they hurt along the way and in fact typically feel that their actions are an entitlement. They cannot tell the difference between doing the right thing and wronging somebody. They are propelled by self-fulfillment.

You have changed your ways, you are regretful about your past, and you probably feel that you can be a good person and future wife. But if he has deceived others, will he deceive you, too?

You now have this guy all to yourself. Look at him and examine his past as you would any other guy who could be in your life. Would your questions about him be the same? Examine who he is right now, but since you have both been in the same group and share history together, you also need to have a conversation about that period in your lives. Investigate any other relationships he has had. Find out how stable he really is and how tolerant he is about the people who have been in his life but who are no longer a part of it.

If it all checks out in a way that you feel comfortable enough to go forward with him, you need to be prepared that this is not the type of guy who will want to work on a relationship if there are issues, as you might be willing to do.

My main concern, however, is about you. For some, the excitement in dating is the thrill of the chase, even for women. Please also ask yourself if you would like to find a way out of this relationship. I am sensing a lack of trust. Trust is the major foundation in a relationship. And that will have to come from you.

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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