I am a 30-year-old attorney working in a prestigious law firm. There is a frum girl who works there too, whom I am very interested in. I’m not sure if she is interested in dating me or likes me as a person.

I very much wanted to get to know her, and for her to like me enough to date, so about three months ago I decided to tell her that I moonlight as a shadchan and have made a few shidduchim. When she heard this, all of a sudden she kept making excuses to talk to me. I figured this was my “green light.”

I began to actually redt her shidduchim of guys that I knew would say no to her. I know that it’s not the most ethical thing to do, but my intentions were good.

I am crazy about this girl. She is gorgeous and smart, and “dresses to kill.” My question is how do I go about letting her know that I am interested in personally dating her? Because this is a secular firm, I can’t ask anyone else to intervene. And I don’t know anyone from her community who can speak to her on my behalf.


By Baila Sebrow

I am not going to scold you for pretending to be a shadchan as an excuse to get to know this girl. There are many people who have actually gone on to become popular shadchanim because their initial intention was to find a shidduch for themselves or a family member. In fact, a large number of people who attend shidduch meetings do so for personal reasons. These people end up assisting others when they hear that a certain name might be a good idea for a particular person. There are countless stories of this nature. In such cases, the end justifies the means on all accounts.

Before I advise you on your dilemma, I will express my disappointment over the selfish and cruel manner in which you treated this girl whom you claim to be “crazy” about. In your quest to claim this girl for a personal date, you were insensitive to the pain you caused her by suggesting names of guys you knew would reject her. And from the way you are describing the scenario, it appears that she was aware that these guys said no.

You justify your unethical behavior by saying that your intentions were good. Good for whom? It was certainly not good for this girl. Receiving numerous rejections can place even the most emotionally strong person in a state of melancholy. What about this girl’s morale? I guarantee that she is feeling very bad about herself, as you have without doubt caused her to suffer some loss of self-esteem. Forgive me for criticizing you so strongly, but it is important for you understand what you have caused to happen to someone you claim to have feelings for.

With the best interests of this girl in mind, I will give you the benefit of the doubt that you did not clearly think through the consequences of your actions. Therefore, this situation needs to be viewed from an angle where a happy ending is possible–despite an unbalanced beginning.

Forget about trying to find someone to intervene on your behalf. You have clearly passed the threshold of mock or real shyness, as you are not just this girl’s co-worker, but also shadchan and adviser. Since a strong rapport has developed between you and her, you will need to practice your moonlighting trade of being a shadchan on your own behalf.

While talking about shidduchim during your personal “coffee klatches” with this girl, suggest yourself as a potential date that she might want to consider. Before doing so, emphasize to her how you feel about the rapport between the two of you. Explain that since you seem to be “hitting it off” together, there is the possibility that you are shidduch-compatible.

I know how “crazy” you are about this girl, but remember that at the end of the day, you are both still going to continue working in the same firm. Therefore, be very objective as you intuitively attempt to read her expression and response to your suggestion.

If she conveys that her interest in you is nothing more than as a person she enjoys chatting with, I strongly advise you to leave it at that. Do not make her and everyone else in the firm uncomfortable by visibly exhibiting signs of unrequited love, as that could seriously affect your superiors’ outlook of your performance as an employee. In addition, at that point it is not necessary to confess that you have been untruthful in portraying yourself as a shadchan. There will be nothing gained–except resentment from a fellow employee. A word of caution: do not ever redt to this girl a shidduch again.

On the other hand, if it turns out that she shares your feelings, I advise you to tread with care. If you do eventually wind up going out with her, you should gently acknowledge that your strong feelings for her caused you to do something that you are ashamed of. Being that we live in a small world, there is always the possibility that she might somehow find out that you deliberately redt her boys who would say no. Therefore, it would be a healthy decision to disclose your indiscretion.

That said, with great tenderness and taking full responsibility for your actions, communicate to this girl that you acted as a shadchan in the hopes that she would get to know you and become interested in you, and beg for her forgiveness for causing her pain by suggesting incompatible shidduchim that resulted in her being rejected.

Yes, you are taking a big chance that she might initially be shocked that you used a deceptive mode to get her to go out with you. But, if she actually does like you as much as you like her, the shock might dissipate, and you will ultimately be grateful that you chose to follow the old maxim of “honesty is the best policy.”

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis. She can be reached at v

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