Ask the Shadchan

jewish dating

To the Shadchan:


My younger brother is having a problem with shidduchim. He is 22 and in yeshiva, although he plans to go to college soon. He would like to get married and has gone out with nine girls, so far. They all said no to him. My brother is sweet, kind, good looking, a decent student – an all-around nice guy. We come from a good, simple family, although with no yichus to speak of.

He went out with each girl two or three times, and liked them all. Each time he was rejected, it came as a total surprise. He was not attuned to how the girl felt during the dates, and had no idea why she said no. 

It’s hard for me to see my brother deflated like this. I feel so bad to see his enthusiasm dashed again and again. I would like to guide him, but I don’t know what he’s doing wrong. Maybe he’s not doing anything wrong; maybe I should keep my mouth shut and just have confidence that he’ll eventually meet the right girl.

Do you have any suggestions about how I, as an older sister, can help my brother?


The Shadchan Answers:


Many times during my years of redting shidduchim, I have wanted to be a fly on the wall, to see what really transpired on a date. Since that is not possible, I have to rely on what the daters report.

Your brother is 22 years old and has dated several girls, going out two or three times with each. He cannot “read” them on a date and then is quite surprised when they reject him. It may be of comfort to you to know that he is not the only person to whom this has happened, and that each date and each shidduch brings him one step closer to his bashert.

That said, several questions occur to me:

1) Is it always the same shadchan or different ones? He may be relying on a shadchan who is suggesting inappropriate matches or who is not able to provide feedback and guidance.

2) Has your brother ever been told the reason he was rejected, or was the shadchan afraid to hurt his feelings? This is very important, because if he is mature enough to hear the real reason and accept criticism along with the compliments, it could help him in the future. I have often pointed things out to individuals, so that they would know what not to do on the next date. Once, a girl I fixed up told me that the young man agreed with everything she said; she did not want someone who always agreed with her. So when the boy called me, I mentioned that – and you guessed it – on the next date, he disagreed with everything. The girl figured out that I had spoken to him, but all ended well.

3) Then there is the possibility that, at 22, your brother is too young and immature in the eyes of some of the girls. It is known that girls are more mature than boys at that age. You mention that he wants to go to college, but does he know what he wants to major in? Does he have a specific goal, or has he not yet decided? This may come across as wishy-washy, and could be a major issue with the girls.

4) Is your brother worldly at all? Does he know what is going on outside the yeshiva walls? Are he and the girl on the same page in terms of hashkafa? It could be that one girl feels she is frummer than he is, and another one feels that he is too frum for her.

5) Does he practice social etiquette, which includes such actions as walking her to her door after the date? Girls are often very hung up on these niceties. Does he spend money on her, even if it is just offering to buy her a drink? Are all their dates “serious,” where they just sit and talk? I always recommend that daters engage in fun activities, which helps them relax and also allows them to see each other in various settings and circumstances.

Here is a plan for helping your brother, although you both have to be willing to “role play” and see where it takes you. It’s called “let’s pretend,” where you go on a “date” with your brother. It could be in a hotel lobby, or even just your house. Sit down and talk as if you were on a date and observe what he speaks about, how he acts, and how he responds. Does he joke? Is he serious? Are there any annoying mannerisms? Do this for an hour, if possible. Take note of things that might be a deterrent to a girl, and discuss them afterwards. Also give him some positive feedback and any tips you think of. In addition you can suggest that he meet with a dating coach.

By the way, I don’t think the fact that your family is simple and without yichus has anything to do with it. Many families would be happy to join with your family. This should not be a hindrance in any way.

You ask whether you should be quiet and just hope for the best. I think you should not be quiet. You don’t want him to become more deflated, so that he will refuse to continue dating. Encourage him, but don’t push him. You can be confident that he will meet the right girl. It may take awhile, but as you know, a bas kol comes out 40 days before a baby is born with each person’s mate. There is someone out there for your brother, even if it takes a year or two before he meets her. In the meantime, he should continue his education and figure out a plan, so that when he goes out again and a girl asks him what he wants to do, he will have a definite answer and come across as strong and resolute, not vague and indecisive.

I hope I have given you some insight in how to handle the situation. I wish both of you hatzlacha and all the best. Hopefully he will be going to the chupah very soon.


Readers are encouraged to submit any questions for Mashe Katz to


comments powered by Disqus