By Baila Sebrow



I have a past that I’m not proud of. During that time in my life, I dated a woman and I was very much in love with her. We got along so well in every way. But I worked hard on myself, and I turned my life around to be a better person, while she continued to live her life the same way she was used to. I needed people to see that I completely turned my life around, so I broke up with her. Also, I didn’t feel like we belonged together anymore.

I am now dating a new woman who is perfect. I felt like the luckiest man in the world that she even wanted to go out with me. Not only is she beautiful, but she comes from a respected family. She knows about my past, but she accepts me for who I am now. We have a blast when we are together and when we talk on the phone. The problem is that I can’t get the other woman out of my head. This woman knows all about it, because I told her about the fun times we had when we were together. She is not happy to hear me talk about her, but I can’t help it. We even got into fights about it.

I am thinking of breaking up with this woman to go back to the other woman, but everyone tells me that I’m crazy and I will never find someone like her. Also, I don’t feel the same way about her now as when we first met. I thought I loved her, but now I am not so sure. I am very mixed up.


It sounds like you never got the first woman out of your system before you started dating the woman you are with now, even if a fair amount of time could have passed between the relationships. One reason might be because although you have changed your life on the outside, who you are emotionally and intellectually will probably always remain. At the end of the day, people are typically drawn to the familiar characteristics of those who are more like them. Perhaps you are not able to make a life with the second woman because, deep down, you are not compatible with her.

You can appreciate all her wonderful qualities and enjoy her company because she is the type of woman who can provide all that for a man; however, when you are with her, you are likely living a double life. Any person who has ever pretended to be someone he is not has only been able to keep up that sham for a temporary period. You do not say how long you are dating this woman, but my guess is that it is long enough for you to feel the pressure of not being yourself in her company.

I get the impression that subconsciously you were hoping she would break up with you. After all, why else would you bring up that other woman when in her company? And talking in such a positive way about the other woman to the woman you are dating, by describing the fun times you had together, is quite cruel. Why would you do such a thing to someone who has been nice to you and accepted you for who you are today without judging you for your past? It is quite unusual to find someone with such traits.

You are clearly torn and don’t know which way to turn. You also don’t want to be alone, and you realize that you cannot have both women. Your first obligation at this point is to the woman you are presently dating. You owe it to her to tell her exactly what’s going on. I understand that you are contemplating breaking up with her, but before you do that, you need to have an honest, heart-to-heart conversation. She has already been clued in to your feelings about woman number one, so it won’t come as a complete shock to her when you discuss it with her in full detail.

How that will turn out will depend on how she really feels about you. If she cares enough about you and the relationship, she may try to convince you to work it out together. My advice would be for you make that attempt. In such circumstances, it is a good idea to reach out to a relationship expert to help the two of you sort things out. If you are somehow able to salvage the relationship, that’s great. However, if after the counseling it becomes evident that you need to go your separate ways, then at least you will both know that you tried to make it work and have the proper closure to move forward.

That brings me to the first woman in your life, the one who made you so happy that when you fixed up your life you felt compelled to break up with her. Yes, I am deliberately being facetious. Think back to what happened at that time. When you realized that your lifestyle was not the way you wanted to continue living, she, on the other hand, remained complacent. Did you offer her the choice to change her life around, too? Meaning, did you tell her that you are a changed man for the better, and unless she makes some attempt in that department, you will end the relationship?

From your cavalier manner about how you went about handling both relationships, I am taking the liberty in assuming that you told her that it’s over because you are a changed man. She might have gotten the drift that you are ashamed of her. That is why I believe you chose the second woman, a person who can validate that you are now an upstanding citizen. And, as we know, that couldn’t work for you either.

What makes you think that the first woman will want you back? And even if she does, what exactly do you hope to gain from that relationship? If she is still the way she was, comparable to who you were when you dated her, then going back to her will result in your realizing that it ultimately won’t work. And then what? Will you then think of running back to woman number two to try again?

Unless that first woman changed her lifestyle in a way that you will feel proud to be with her, it is best to leave things status quo. If she somehow hears that you are now available and reaches out to you, then you will have to find out how she lives her life. If it’s as she has in the past, then my opinion of leaving things alone still holds. And if she wants you back, she may promise to change as you want, but you will have to accept that she may not mean it, or she may at some point return to the way she was.

When one is chozer b’teshuvah, when it comes to choosing a life partner the challenges are that much greater. It is not just about finding someone who is compatible with who you are now, but finding someone who also understands where you are coming from. That said, the primary idea is to stick to what you are used to. In this case, I refer to the old saying, “Like attracts like.”

Dating a woman who was brought up in a culturally similar environment will at least ensure that you will “get” each other. It comes down to truly understanding things in the same way. That type of compatibility serves well in the future when situations arise, and you are placed in a position of having to deal with them in an undisputed approach. One’s background will have a major impact on how he or she reacts to and addresses a situation.

It would be in your best interest to find a woman who has lived a lifestyle similar to your past ways but has moved on to being in a better place in life. I will also caution you that whoever this woman turns out to be, she needs to feel comfortable and happy with her newfound lifestyle. There are cases where one changes for the better, but as soon as something challenging happens, they go right back to the way they were. From what I gather, you are steadfast in your lifestyle, and you need to make sure that whoever you allow into your life is just as strongly committed to a sincere, upstanding life, no matter what.

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


Please enter your comment!
Please enter your name here