To the Shadchan:

I have a close friend who will soon be entering the shidduch parsha. This guy has a great head for learning, wonderful aspirations for a future in Torah and chinuch (education), and is handsome too. There’s only one problem: He has emotional issues that will very likely hamper him when it comes to this parsha. During different stages of my relationship with this bachur, I’ve seen him beat himself up verbally on one end of the spectrum, and be manipulative towards others (including me) on the other end of the spectrum.

I care too much about this friend not to say anything, but I don’t know what to say or how to say it! It’s quite possible that he might even need the help of a professional, but again, how could I broach this subject. Any advice would be appreciated!

To the Shadchan:

Thank you for your very helpful columns about shidduchim. You are the epitome of sechel. Now that our oldest son is starting in shidduchim, we are flabbergasted at all the new “rules.” It seems like a different world today than when we went out. If you step out of the box, everybody looks at you, saying you are not yeshivishe enough, not this-or-that enough, etc.  For example, calling the girl before the first date is now taboo. It doesn’t make sense that the shadchan has to be the one to set it up; we feel if you are old enough and mature enough to get married, you should certainly be able to make a short phone call. We didn’t like it but ended up going along with the crowd.

To the Shadchan:

I am what you would call an older single, a successful professional in my early 40s. I am reasonably good looking and have lots of friends. I think I am a nice guy. I treat a woman well. I’m not cheap and am always willing to travel to wherever she is located. 

As you can imagine, I’ve dated quite a few women. Many of them did not want to continue seeing me, and many of those who wanted a relationship, I wasn’t interested in. I don’t think I’m overly “picky.” I’m looking for a regular, nice girl. She doesn’t have to be a beauty, although she should be attractive to me, of course. One thing I do not want is someone who is a super-achiever. Some of the women I have met have become too sharp and efficient for me over the years they’ve been single. My belief is that I am not married because I have not yet found the right one, and I do still hope to find her. 

To the Shadchan:

I am 23 years old and have been dating since I was 20. Last year, I met a guy I really liked. We connected on many levels. We went out around 10 times, and he seemed to like me too. It might sound weird, but I was sure we would be getting engaged and was already planning our life in my mind, when, all of a sudden, he broke it off.

During the phone call, he was very brief. He didn’t offer a reason, and I was in such shock that I didn’t think to ask him for one. I called the original shadchan, but she had dropped out after the second date and said she couldn’t help me. To this day, I do not know what happened and why he refused.

To the Shadchan:

I have been inquiring about a young man who was redt to my daughter. I happened to meet a friend of mine who is a teacher and taught him in 10th grade. This boy seems to have been a troublemaker at that age. My friend could not say anything nice about him. She told me he was chutzpadik and gave her a hard time.This young man is 23 now. He is a professional, who is working after learning in yeshiva for a few years. More recent references have only good things to say about him. It seems he is a hard worker with good middos. He comes from a good family, and everything checks out okay.

My question is how much credence should I give to the teacher’s words. Maybe the attributes that made him behave badly when he was 15 are deeply ingrained character defects that are still relevant. Or maybe he is now using his chutzpa, etc. for good things. How can I find out which scenario is the correct one? Or should I chalk it all up to being a teenager?

If you think that information from the past is relevant, what would be the cut-off age, before which we should not take information seriously? Obviously, no one would pay attention to the way a person behaved when he was in kindergarten. Or would they? I would appreciate your advice and opinion.

Tu B’Av, the 15th day of Av, is approaching as I write, and Yom Kippur is not far behind. These were joyous days in ancient times as the girls went out to the vineyards in borrowed white dresses and danced, exhorting the young men to choose their zivug. We don’t make shidduchim that way anymore – for better or worse! – but I have been making shidduchim long enough to have seen many other changes over the years of my “career.” So, taking a break from the usual question-and-answer format of this column, I will instead try to answer a question I have been asked many times: How has the shidduch world changed?

Let me start by describing the frum community through the eyes of a girl born in Ohio. It was very different from today. Cleveland was a midbar (desert) in the years of my youth, as were all the cities in the United States except for New York. The frum population was extremely small, with few eligible boys or girls in town.