To the Shadchan:

My older daughter got married a few years ago. The whole shidduch process went very smoothly for all of us. She was a typical kind of girl. She went to a typical seminary in Israel, came back, and started to work and go out. She had lots of friends like herself, and she wanted a typical type of boy.

My second daughter now wants to start dating. She is more of a loner, who does not have a lot of friends. There is something a little atypical about her. For instance, she doesn’t seem to be aware of fashion. (She likes to wear hats in the winter, which makes her “different,” silly as that may sound.) She also tends to be moody and emotional.

To the Shadchan,
I have brother-in-law who is a popular and outgoing person. Unfortunately, he is also a loudmouth, saying whatever happens to cross his mind without thinking. As you can tell, I am not fond of him. Lately, I’ve become aware that people doing shidduch research are calling him about me, even though he is not on my list of references. I am having trouble getting dates, and I have reason to believe that my brother-in-law is saying not nice things about me. I have asked my sister what he says, but she does not want to be in the middle.

I’m not necessarily accusing him of maliciousness. But he is not a refined person, and I can just imagine how he talks. Anyone who deals with shidduchim knows that when you give information, you need to emphasize the positive and present any negatives in a positive light. My brother-in-law just blurts things out.

To the Shadchan:

I am a 26-year-old, nice, normal guy, and I am having an issue with commitment. I think the problem is that I have a number of divorced friends, and that number seems to be growing. My parents are happily married, as are my two married sisters – at least I think they are – but this divorce thing scares me.

What typically happens is that I go out about 10 times, and I really like the girl. But then, as I am getting ready to move to the next step, I start to see the bad traits. These could be a high level of anxiety, temper, putting others down, or just plain selfishness. I don’t see these issues in the beginning.

I am fairly new to dating, and I’d like to ask you about some of the etiquette dilemmas I’ve encountered so far.

I went out with a boy I really liked, and I wanted my mother to call the shadchan right away to say that I wanted to go out again. My mother said that the boy’s side is supposed to call first, and that we should wait for the shachan to call us with his reaction. I was nervous and not my best self on the date, and I wanted the shadchan to be aware of that, in case the boy said he didn’t have a good time or that I was too quiet. That way, she would be better prepared to urge him to give it another chance. I also wanted to hurry things along, because the shadchan sometimes takes a long time to call back. Is there such a “rule” about who is supposed to call whom and when? What’s the point of it? (By the way, my mother did not call, but we did go out again, and it didn’t work out anyway.)

To the Shadchan:

I’m almost 20, and my father says that “we” aren’t ready to start dating. What might be more accurate is that he is not ready for me to start dating, because he is scarred from his involvement in my sister’s dating experience. My father watched, feeling both hopeless and helpless, as my older sister entered an unhealthy marriage. Her marriage ended in divorce, but baruch Hashem, a few years later, my sister is happily married and flourishing in her beautiful new marriage! My sister has already replaced hard times with stunning memories and a bright future, but my father has not been able to do the same.

To the Shadchan:

I am listed as a reference on the resumes of a few of my friends, and I get called fairly often to describe a girl to a prospective mother-in-law. I know how important it is to be positive, but I also want to tell the truth. Recently, a mother called me and asked a question that I didn’t know how to answer. Actually, I was speechless.

 This was a boy who was considered a prize, and lots of girls wanted to get a date with him. The mother asked me many questions to determine whether my friend – let’s call her Shoshi – would be suitable for her son. The last question was, “How would your friend react if she found out she was infertile? What if she had triplets after just a year of marriage? What would be her attitude?” I didn’t know what to answer. Should I say what I thought the mother wanted to hear? I wasn’t sure what that was. Should I make up something? I couldn’t do that. The question was unanswerable, anyway. After all, how could I possibly know how anyone would react in such made-up situations? How can I know how I myself would feel?