By Baila Sebrow



I am a 27-year-old woman, and I’ve never been married, though I was engaged once. It feels like I went out with every guy out there, or at least looked into every guy out there. I never felt anything for any of them, even the guy I was engaged to. Then I met the most awesome guy. He is handsome, sensitive, funny, smart — you name it. He is exactly what I have been looking for all these years.

Here is what’s going on. He is divorced and has kids. Everyone I know is telling me that he is bad news because he is divorced and has kids. They all say that if he was that good, he would still be married. And now everyone is sending me guys to go out with that I have no interest in. They really think that I can just drop a guy I really like because they send me a few doctors or rich guys?

The only people who agree with me are my coworkers. I think they know me better than any of my family and friends. They are sophisticated and worldly, just like me. They also met my boyfriend, and they think he is great and that I should not listen to anyone and instead do whatever makes me happy.

The real reason everyone else is against him is because of that one mistake he made in his life. Big deal! So he is divorced.

This guy told that he wants to marry me but is waiting to make a real proposal when he knows everyone will be happy about it, instead of now, when everyone is ganging up against us. He knows that it would mean so much to me. What can you advise me?


I get the sense that regardless of how awesome this guy is, you might be somewhat ambivalent about this match, and that could also make him uncomfortable. That is not unusual, especially when the people in your life who mean a lot to you are antagonistic about the relationship.

You say that the people you work with are sophisticated and worldly, but in all fairness, you probably know them only from a professional perspective. I am sure they conduct themselves with the integrity that is expected of them in the workplace, as you undoubtedly do. That said, I believe it is reasonable to assume that they do not know who you are in your personal life when you are not in their company.

The advice you are receiving from them is likely based on some romantic notion that if you meet someone you love, throw caution to the wind and go live your life. That is very easy advice to offer somebody who is not a family member or whom you do not care all too much about with regard to what the future will bring. I think you understand exactly what I am talking about.

Before I go into the feelings of your family and friends, you need to recognize how this guy has lived his life prior to your entrance into it. People who get married for the first time, especially when they are young, are all starry-eyed. Yes, even those who are worldly and sophisticated. Being in love and hopeful for the future softens the most emotionally controlled person. Watch a happy chassan and kallah during their engagement period and you will agree with what I am saying. Those who have been through a marriage and have children cannot react the same way. It’s not about feeling less love for the person in their life, but they are coming from a different place. Experiences shape and change people. So, even though you have been engaged before, you still have not been married and raised children. You and this guy might share compatibility in every other area of life, but the fact remains that you are coming from emotionally diverse places. Not only that, but you will also become an instant mother to his children as soon as he puts that wedding ring on your finger.

I am not trying to discourage you from pursuing your relationship and accepting a proposal from him. On the contrary, I am a firm believer that if the circumstances surrounding a couple are feasible for them, then I would say all systems go. I have been a shaliach many times in making matches where one of the parties was divorced while the other had never been married. But since you are asking for advice, I need to depict an objective picture of what you are dealing with.

Although you have never been married, you have been through challenges in the relationship area of your life. You know the dating scene, and you’ve experienced a broken engagement, so when you met this guy you must have felt that things were finally going to go right for you. The fact that he has lived a family life automatically gives him the wisdom of experience and an easygoing manner about dating. Meaning, he is probably not as uptight in dating as somebody who has never been married. I hear that a lot from singles who claim that when they date a divorced person, they have a much better time on a date.

Yes, this guy seems different because he has already experienced life as a husband and father. He knows how to make you feel secure like nobody else you have dated before. Not only that, but he surely demonstrates the kind of confidence that you have not seen with any other young man. He is not coy or awkward while on a date. Going through the trauma of a divorce and raising children from that marriage usually takes away any clumsy demeanor in dating.

When I mentioned earlier that you will become an instant mother the minute you marry him, that concept might have seemed like a fun idea. I have heard young women express that notion. What they do not realize, and perhaps what you also may not realize, is that such a marriage is not about playing house. As the stepmother, you will have to take on and share the physical, emotional, and financial responsibilities of caring for his children. And that is not all. You need to be prepared to accept the ongoing communication with his ex-wife — and that is when the divorce is amicable and the exes get along with one another. You cannot imagine the stress that comes when the divorced parties fight. The new spouse typically ends up feeling like an outsider in his or her own home in such a circumstance.

By marrying this guy, you will essentially be entering a marriage of this nature. This is not about anyone holding a one-time mistake against him. He might turn out to be a more devoted and wonderful husband than anyone you will ever know. The question is if you will be able to psychologically tolerate a setting of children, ex-wife, unexpected financial pressure, and everything else that comes along with your new husband from the moment you become a wife to him.

Now let’s talk about your family and friends. I have a hunch that they are thinking along these lines or perhaps even expressed the same opinion about this guy and the relationship you have with him. If you would tell me that only specific people are against him, I would tell you to do whatever makes you happy. But when so many people are saying the same thing, you have to believe that the whole world, outside the people you work with, cannot all be wrong.

I will throw something else out there for you. Is it possible that it is not about this guy being divorced with kids that is the real issue? Is there something else to his story that you have not disclosed to me? Is it possible that your loved ones heard rumors about him, and he dismissed them as untrue, and being that you care so much about him you chose to believe what he says above anyone else’s input?

If somebody wants to exert themselves a bit, they can find out everything they need to know about anyone. No, I am not telling you to go do a search on him on the internet and be satisfied with what you read. Use the old-fashioned method, with some sophistication.

Speak to people who knew this guy while he was married to his ex-wife. With respect to rabbis, you might be wasting your time if you go to his shul to ask about him. The rabbi there will only know the side he presents in shul. Speak to people who have seen him interact as a married man. If he lives in a different community now, go to the community he lived in and ask questions. Do not, under any circumstances, ask current neighbors who first got to know him as a divorced man. That would be another waste of time. Speak to old neighbors. Reach out to parents of children with whom his children have had playdates or went to school. I promise you that you will get a story. You can then weigh what you hear with what you presently know. In the end, it might turn out that whatever it is, you will still feel comfortable enough to deal with it, or maybe not.

If you ultimately discover that this relationship is not for you, then even though you dated many guys and have gotten countless suggestions, consider revisiting those prior suggestions. I am just putting that out there for you to keep in the back of your head.

In conclusion, this guy might be right for you, and your family and friends may just want you to marry a guy similar to you who has never been married. If so, they may need to recognize that since the stigma of divorce has lessened in the frum community, people do not stick it out in a marriage that is not working for them, as they might have done in previous generations. Perhaps this guy was married to a woman who was impossible to live with. Or it could be that this is a case of two people who never should have gotten married in the first place, recognized that fact, and subsequently ended the marriage. He may have tried to make the marriage work, but in the end it was not salvageable. As long as you have the full story, and you walk into this marriage with your eyes wide open instead of with stars in your eyes, there is no reason why you should not be able to have a successful union with him.

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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