By Baila Sebrow



I have been reading your column in the 5TJT but I haven’t come across my particular question. Although I have guidance from my rabbi and seminary mentor, they’re quite yeshivish and I’m not sure they’d relate. So I’m turning to you for advice.

I’ve had a hard time dating. I’m turning 32 in a few days, and I’m a ba’alas teshuvah (of nearly seven years now). When I thought I was finally getting married, something big came up — the guy, who’s frum from birth, was never married, is my age, and came from good family, had surrounded himself with bad influences and was chasing non-Jewish women behind my back — and that fell apart. I was devastated, but now that’s in the past.

I was recently introduced to someone else. He’s nine years older than me, also frum from birth, and was never married. He’s definitely more modern than I am (I consider myself to be modern, but he’s way more). He’s observant and considers himself Modern Orthodox. But despite that I’m more modern than my yeshivish community (I attend university and would also like to pursue a graduate degree), currently, I’d still be more comfortable in my community than in his.

What can I do to not self-sabotage? I am aware that this relationship may not go anywhere (it’s just in its beginning, and maybe we’ll find out we’re not for each other), but I hate to think that I could miss out on getting married to someone who would be for me just because of community differences or another superficial thing.


When people sabotage their relationships, in most cases it is usually the subconscious acting in accordance with what they really want but do not feel courageous enough to carry it out in a mature manner. So instead, they appear to walk the walk and talk the talk on the outside, but they will create situations that will cause the person they are in a relationship with to back out.

Time and again, I meet attractive, put-together, accomplished men and women from normal, healthy backgrounds who tell me they are unable to sustain a relationship. And when I ask them what went wrong that caused their relationships to end, they tell me that the other party got cold feet or backed out for something that was just a misunderstanding.

It happens that someone can back out of a seemingly good relationship for reasons that might not be well understood, and, yes, people do get cold feet, but when the same thing happens to a person over and over again—when it is clear that there is a pattern—there is cause to analyze and examine why this keeps happening.

I am impressed that you are astute in recognizing your potential for self-sabotage. That said, we need to do two things here. The first is to find out if you are capable of self-sabotaging and why, and the second is to evaluate whether this new relationship merits exploring further.

You have been through quite a bit. Becoming a ba’alas teshuvah is no minor achievement. It means giving up what you have known and were raised with. Not only that, but becoming a BT is taking upon yourself prohibitions and a new lifestyle, with new people to whom you will turn for advice and acceptance. That is emotionally taxing for even the strongest person. When you thought that you were ready to get married, the man with whom you were prepared to spend the rest of your life did something so shocking and despicable that it left you devastated. You are now so shell-shocked and likely emotionally fragile that you might be afraid to trust a man again. If that’s true, nobody can blame you.

I would like you to understand that what that man did had nothing to do with you as a person. You did nothing to bring that on, except that you trusted a phony person from a good family who deceived you. Specifically because you are a BT and he’s an FFB who walked on the wrong track of life, he likely thought that he could pull off his crooked ways on you and get away with it.

It is not uncommon for such men to deliberately seek relationships with women who have no way of finding out who they really are. It goes further than that. You don’t say how you met him, but it would not surprise me if a shadchan or other trustworthy person was the one who introduced you to him, believing that he was a solidly good man. It is also possible that they may have known certain negative things about him, but they chose not to share that with you. Not that anyone was trying to hurt you, G-d forbid, but folks like that guy tend to pretend that they are mending their ways and people believe them and feel that a BT would therefore make a good match. At the risk of sounding redundant, I will reiterate that there is nothing you could have done differently to change the outcome of that relationship. He is who he is, and that has nothing to do with you. Baruch Hashem, you discovered the truth before marrying him and not after. At this point and going forward, he no longer exists in your world.

You now have a new man in your life. Granted, it’s still in the beginning stages and can go either way, just as it could for anybody else. Whatever you consider more modern than you should make no difference, because, as you say, he is observant. Interestingly, later on in your letter, you claim the differences that you see in him are really just community customs. Does he wear a kippah serugah while the men in your community wear suede or velvet yarmulkes? Or does he wear colored shirts while the men in your community wear only white shirts?

If those examples are accurate, do you believe that’s what it takes to be a trustworthy, quality person? I think that by now you know better! Are you afraid that your rabbi and seminary mentor will disapprove of your relationship with this new guy because he is more modern? Did they approve of the other guy who cheated with non-Jewish women behind your back? I may get flak for saying this, but perhaps you need to find new mentorship in your life before you go any further. Perhaps they are no longer a match for you.

I can see why you would (unknowingly) self-sabotage a relationship with a man who might ultimately be good for you. By doing so, you won’t have to worry about the approval from your rabbi and seminary mentor, and the decision of choosing between them and this guy is no longer yours. Your subconscious would be taking care of it for you.

My advice is for you to continue dating this man while being your best self. It doesn’t sound like he has any issues with your continuing education, and it also doesn’t sound like he minds that you feel more comfortable living in your community than in his. You have been through so many changes in your life and it stands to reason that as long as you feel settled where you live, it is probably best that you remain there. However, that doesn’t mean that you need to follow the masses with respect to the person you marry.

I can understand why you feel the need for approval and acceptance from your community, and I believe that you can still have that and the man, too. If you are planning to ask your more yeshivish cronies what they think of him, you can expect that they might find a reason for you to nix him. It’s all in the way you present it to them.

Tell your advisers that you are dating a man who is shomer Torah u’mitzvos, and that he is a good and sincere person. Stress how happy you are that you met him, especially after all you have been through with that other failure. You can then say that the only difference is his way of dressing, or whatever else you consider superficial. They will likely ask to meet him, and if the relationship progresses to the point where you feel comfortable showing him off, then if he is good to you, he will probably make a favorable impression on them, too. My guess is that it will all work out in the end. However, if these people you are so concerned about are narrow-minded, then my opinion, as I said earlier, is to find new hadrachah.

You were given another chance at happiness. Grab it. You have only one life to live right now and it’s your own. Maximize it to its full potential.

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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