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.

 I was going out for a few months with a girl whom I really liked. I was just biding my time and waiting to pop the question. To my great shock, I got a phone call from the shadchan, who told me that the girl did not want to continue dating. She did not tell me a specific reason but simply said that she feels I am not for her. She did not even have the courtesy to tell me herself but went through the shadchan!

I know I am not the first to be rejected, but that doesn’t help me feel better. At this point, about four months later, I just don’t have the energy to start all over again. I invested so much in the relationship, and told her things I had never told anyone before. I feel like I was punched in the stomach. The few times I’ve dated since this happened, I said no after the first date. I am afraid to go through this again. Any suggestions or ideas to help me get over this and move on?

I am a graduate of Bais Yaakov in my third year of shidduchim. Although dates don’t come easily to girls, as we all know, I have had my share. Yet I look around at age 23, still here, and wonder what might be holding me back.

I read a book that has been making the rounds of my friends. It is a secular book about how to “land a husband.” It is all about how to “market” yourself. Its advice on how to act during a date ranges from exactly how to tilt your head to ways of responding to your date’s conversation. I had my doubts about this method, but I wanted to do my best to maximize my chances.

To the Shadchan:

I am recently married and living in New York. Remembering my days as a single, I have started setting up people. I’ve noticed that many men do not want to travel to date. These are mostly working guys, aged 25 to 35, who live in New York and have never been married. I have suggested women who live out of town, and their response was, “I will only date women in New York.” Some men go as far as to tell me that they will only date women who agree to meet them in Manhattan, where they work.

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. 

To the Shadchan:

My son, who is in yeshiva, just turned 21. Like me, he has seen the ads and articles in various publications about the shidduch crisis, including the idea that boys should get married at a younger age. (The assumption is that eliminating the age gap between boys and girls would help equalize the numbers of boys and girls in the “market.”)

He is not asking me to help him find a wife, so maybe he is not ready yet – although I get the feeling he is worried about it. I, too, am not sure he is ready to get married. But looking ahead, I am thinking about what to say if he does bring it up. Normally, I would encourage him to wait until he is older, but I am wondering whether these ads apply to him. How would I know if he is ready to get married? What kinds of qualities in him should I be looking for? How can he and I know when would be the right time to start searching?

I occasionally insert the topic of “what kind of girl are you looking for” into our conversations. Should I continue that, or should I avoid it, so as not to encourage him to pursue marriage at this time? Any guidance you can give me would be appreciated.