Ask the Shadchan


To the Shachan:

I have been on a few dates with a boy who is nice but – at this point, anyway – nothing special. We get along very well, and the conversation flows nicely. Although his looks as well as everything else about him are average, I would be willing to keep dating him, as I feel he could grow on me over time. The only thing is that I just got a “yes” from another boy, who is a real “catch.” Everyone says he is a top boy with great middos. He is also personable, wealthy, and very good looking. He is the type of boy you wait a long time to get a date with. I’ve been single for a while and have been hoping for someone like him to come along. I feel I won’t be able to concentrate on the current boy as long as this new boy is in the picture. I am ready to say no to the boy I am dating, because the other one sounds much better. My sister says I am not that young, and dates don’t come as often as I would like. She is strongly urging me to give the current boy a chance and tell the second boy I am busy. We decided to write to you to see what I should do.


The Shadchan Answers:

Your question is not unusual. It happens many times that someone is dating one person when another person comes into the picture. Years ago, when boys traveled to New York to date, it was accepted for them to date two girls at the same time, since they had made such a long trip. Girls, too, dated more than one guy at a time.

I know for a fact that someone dated a girl one night and another girl the next two nights. He went back to the first girl, and they eventually married. The second girl had been redt to him time and again, so he gave it a shot but realized that it was not for him. At first thought, I would tell you to do the same thing, but I know that this is now frowned upon and not considered proper etiquette.

Let’s analyze your current situation. You do not state how old you are or how long you have been dating this young man? Is he still willing to continue with you? If you have had two or three dates, then I can see dropping it. But the way it sounds to me, you have been dating a long time, and now you want to “dump” him.

I would also ask, if you were in the middle of this shidduch, why did you even listen to the other suggestion? You should have told the shadchan that you were busy and to put it on hold. In my dealings with shidduchim, it often happens that I call someone with an idea and they tell me they are busy.

You think that boy #1 will grow on you over time, yet you are ready to drop him in a minute because the one you consider a more attractive choice said yes. How do you know that your “prince charming” will be willing to go more than once? Let’s say you do, and date #2 doesn’t go anywhere. You will be back to square one with no dates at all.

Boy #2 sounds like a great guy – that is, he sounds good on paper. Not everything that sparkles is a diamond, however, and something dull may, when polished, be pure gold.

I would advise you to do a little introspection. Has this happened before? Do you have commitment issues and think that the grass is always greener on the other side? Is this a pattern, where you “love ‘em and leave ‘em,” as they used to say? How would you feel if the shoe were on the other foot and somebody “dumped” you in the hopes of winning another girl who sounds so good on paper?

Your sister is giving you sound advice, but only you know what is best for you. If you feel that you could be happily married to the current boy you are dating and could build a bayis ne’eman beYisrael together, then I would put the other boy out of your mind and concentrate on your current shidduch. If the new prospect is your bashert, he will be there if and when you are ready to date him.

If you don’t feel that way, and are still unsure as to whether the current boy is for you, then it may be best to break it off for now and date the second boy. But beware; you may not have a chance to meet the first boy again. Are you ready for that eventuality? That should be a good barometer for whether or not you should be breaking it off with him at all.

In either case, whatever you decide, I wish you hatzlacha.



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