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?

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.

To the Shadchan:

I recently got engaged to a wonderful boy with a great family. His family is super nice, and I love going over there. I get along so well with his parents and siblings. The only issue, which I am beginning to see and which might be bigger than I realize, is my future mother-in-law. While she is really sweet, she seems controlling. She wants to know every detail of my day. My mother says that she’s just trying to be friendly, but it feels different to me. She is also trying to control every detail of my wedding. Yes, it’s my wedding. I am not trying to sound mean or anything, but the truth is, I have been planning my wedding ever since I was little. I really don’t appreciate someone trying to take away my dream. My chassan supports me and says that we should do it my way, but he would never stand up to his mother. It’s not an issue of money; both my parents and his are quite comfortable, b”H. We just have very different tastes. She is telling me how to do my nails! Should I be worried about her in the future? We will be living in the same city (away from my parents), and I am scared that she will try to run our lives. How should I deal with her in general, without being chutzpadik and ruining my relationship with her?

To the Shadchan:

I am a married 24-year-old guy. My mother is really pushing me to set up my younger sister with my best friend. I would love to – I mean, who wouldn’t want to have his friend for a brother-in-law? So what’s the problem? My friend is a wonderful person, with excellent middos and well educated both in Torah and secular studies. Unfortunately, however, he is bipolar. He told me this and swore me to secrecy. He is usually on meds and is stable, but I just can’t bring myself to fix my sister up with him; there are many difficulties that I would not wish on her. My mother thinks I am being selfish by not helping my sister. How can I tell her that I really am doing the best for my sister, without betraying my friend’s trust?