By Baila Sebrow

By Baila Sebrow


Everyone has been on my case to get married. I have a successful practice, own homes, and give lots of tzedakah to many causes; I want for nothing. But as I neared age 40, my parents started making me miserable and putting me on a major guilt trip that they will die without seeing me married. It wasn’t that I didn’t want to get married. The Orthodox girls were terrible dates, and the non-Orthodox were not much better. I tried dating a few ba’alei teshuvah, but they had their own issues. And then when I least expected it, I was out of town and staying at a Chabad rabbi for Shabbos, and I met a beautiful woman who works in my field.

Here is the catch. She is a recent convert. It doesn’t bother me because she is such a tzadeiket. She will never say a bad word about anyone. She is kind and sincere, and I can’t say enough about who she is. Her family is very respectful, and they totally accept her choice to be Jewish. Incidentally, she was always very devout. She is the most amazing woman I have ever met. However, my parents are having a fit that I want to marry her. They don’t understand why I want to marry someone whom they call a “shiksa,” even though she is now Jewish. They think that I could find somebody like her who was born a Jew. They have no clue what’s really going on in the singles scene.

I know that I don’t need my parents’ approval to get married, but I was wondering if you have any advice, or if you ever came across this type of situation. I also want to mention that this woman is willing to wait if my parents need more time to get to know her and like her for the person she is.

I read your column every week, and I love your sound advice. So whatever you tell me to do, I will definitely listen to you.


I think it’s wonderful that the woman you are dating is so understanding of your needs and sensitive to your dilemma. Had she not been brought up devout in her religion, but rather as someone living in the secular society, she likely would never be able to grasp the challenge you now face.

I have dealt with many situations involving frum-from-birth people marrying converts. And I will tell you that even though everyone was smiling, hugging one another, and kissing at the wedding, making sure to put on the right pretenses, I am privy to the wars that went on behind the scenes prior to that public showing. That said, you are not the first person to fall for a convert. There have been many men and women who have not had much success in dating, and somehow, they met a former non-Jew and finally felt that they met their bashert.

If a Chabad rabbi has supervised her geirus process, then I feel comfortable saying that there is nothing questionable about her geirus (though you should certainly verify that). Rather, my immediate concern is that whatever you do must be for a healthy reason and with the correct intentions. Meaning, although this woman is wonderful and amazing in every way, nobody is perfect; would you give someone from your own circles the same free pass for whatever flaw she may possess? That is a question you need to ponder honestly.

I have a difficult time accepting that every frum-from-birth woman or ba’alas teshuvah you dated was terrible. I will accept, though, that you never felt that same connection with anyone else as you do with her, and much of it likely has to do with the fact that she presents unusually atypical. As an educated, sophisticated man, surely you know that people who are familiar with one another will say and do things they normally would not with someone from a different culture. I see this in many situations where frum people deal with those who are not Jewish. They put on their best behavior. While with their own kind, they are who they are. That is what you were likely finding in your dating career as well. Why am I telling this to you? I want to make sure that you walk into this marriage with your eyes wide open to the fact that people are people, and emotions and characters vary from person to person, regardless of religion.

I can understand that your parents were unhappy that their successful son was not yet married. They probably could not understand why, and it gave them tremendous grief, as it would any parents of single children past a certain age.

I will stress to you that I am fully on your page, and that as a halachic giyores, this woman should be treated with the utmost respect and acceptance. You have my full blessings to go ahead and marry this woman. However, I am not your family. I am not your parents who raised you and had hopes and wishes for you. Orthodox Jewish parents, when it comes to shidduchim for their children, want someone similar to them. This lovely woman is not who they had in mind for you, and they are having a difficult time processing your decision to marry her.

Have you introduced her to any of your friends and colleagues? Have you introduced her to your rav? When it comes to the decision to get married, it is of vital importance that you watch that person interact with those who are close to you and those whose sincere opinions you respect. Find people who appreciate the choices you have made in your life, are open-minded, and have known you for a decent amount of time. After they meet her, find out how they feel about her. If they detect something about her, other than her being a giyores, please respect their opinion and take it into consideration, no different than if she would be from your own circles.

Another aspect to assess is where you were holding emotionally around the time you met this woman. Were you jaded, or had you recently come out of a relationship that left you wounded? Had you totally given up on marriage altogether, or were you in a healthy place of mind, open to the idea that if you met someone with whom you felt a deep connection you would marry her?

For a few minutes, let us go with the notion that it’s all systems go as far this lovely woman is concerned. You may never have your parents’ full acceptance, and you need to make peace with that idea. Hopefully, they will at least be able to put on a good show for the public, as I have witnessed many times. But I would like you to bear in mind that it is possible that they may never be able to do that either. Just as you have the right to do what you want, so do they. My concern is your future shalom bayis because of the struggles their non-acceptance will create. How will everyone else relate to you, and what sort of impact will that have on both of you? Those are discussions you need to have with the woman you plan to marry. She sounds like a smart lady, and she likely understands these issues, which is why she told you that she is willing to wait. She knows that there could be problems on the road ahead, and she wants to make sure that everyone is on board and that you both enjoy a happy, fulfilling marriage.

For now, try to integrate her as much as you can into your family and life. Arrange for your parents to see what a righteous woman she truly is. It is important that they at least get to appreciate her values as a human being, and also her commitment to being an Orthodox Jew. With regard to her family, I understand that they accept her conversion to Orthodox Judaism, but it is equally important that they treat you as a member of their family, too. In fact, if she has siblings, or other close family, how they treat you will undoubtedly have future impact on your relationship with your wife.

I wish I could tell you that at the end of the day, everyone will be living happily ever after. But realistically, that may never be, and if so, you will both have to face that reality and make the best of the situation by remaining respectful to those who matter to you and allowing them to see that you have a strong marriage and that nothing will ever come between the two of you.

I will conclude with this. Of the cases similar to yours with which I am closely familiar, the couples have beautiful marriages and are raising incredible generations of families, setting the foundation for awesome legacies. May Hashem grant you both clarity and revealed good, and you should be zocheh to build a bayis ne’eman b’Yisrael.

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 Baila also hosts The Definitive Rap podcast for and Israel News Talk Radio. Questions and comments for the Dating Forum can be submitted to Read more of Baila Sebrow’s articles at


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