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?

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.