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?  

To the Shadchan:

I am fairly young and newly married. I have many unmarried friends whom I would love to help. B”H, my husband knows a lot of eligible guys. I started fixing people up and then got too frustrated. My friends were too picky and turned people down for no real reason. But since I am friends with them I felt that I couldn’t tell them they were being stupid. These are really top boys. I was recently talking with my mother about this, and she said that I really should get past my feelings and help these girls. Do you think I’m obligated to help, and, if so, do you have any advice for me?

To the Shadchan: I am a 21-year-old, typical Bais Yaakov girl from a stable and happy home. I am going out with a boy. I like him, and everything seems to be going very well; we will be having our seventh date soon. This would seem to be an ideal situation, except that I am very nervous. Twice before, I was in the same situation. I went out with each boy for a long time, and it was going smoothly, with the next step to get engaged. Then, for some reason that I can’t explain, I just couldn’t go on. I want to stress that I liked both boys. But I felt something was not right – I couldn’t even put a finger on what was bothering me – and I couldn’t continue. So, I see from my experience that even if I like the boy, it doesn’t mean anything. I’m very scared that the same thing could happen with this relationship. If I do end up breaking it off, I am worried about all the emotions involved – both his and mine – as well as the reputation I will get. I am also concerned that something might be wrong with me. (I don’t think I am afraid of marriage, but how would I know if I am?) What do you think?

Worried

To the Shadchan:

A shidduch was suggested to me with an American boy who has made aliyah. He sounds like just what I am looking for, and he is interested in meeting me. The problem is that he presumably wants to live in Israel forever, while I am not so sure. I do love Eretz Yisrael and really enjoyed my year there, but I see a few obstacles to making a permanent move. First, I have a hard time with the divisions among different types of Jews and having to choose one derech. Second, I don’t think I would be happy with the school system. In addition, I would miss my family, who would not be able to afford visiting often or sending us tickets to visit them. And finally, I am not fluent in Hebrew, and would probably have a hard time finding a job. I would love to live in Eretz Yisrael for a few years but would most likely want to return to the States eventually. If I’m not sure I can commit to living in Eretz Yisrael long term, should I give up on this shidduch?

To the Shadchan:

I am hoping you can help me with my serious problem. For quite some time now, most of the boys who have been redt (suggested) to me have been saying no. I didn’t understand why, since I am considered a good catch: I am pretty, have a good job, come from a nice family. Still, everyone kept saying no. Recently, a friend told me that a person in town is spreading rumors about me. My friend refuses to tell me who she is, claiming that it would be lashon hara to tell me. How do I handle this?

To the Shadchan:

I must preface this letter by saying that Hashem is really watching over me, b”H, and I am not having that hard a time in shidduchim. While I have not yet found my zivug (mate), I don’t have the horror stories that some girls have in dealing with shadchanim, weight, looks, boys’ mothers, etc. However, I did just come to a bump in the road.

My father told me that his Rav wants to know if I would go out with a certain boy. (We were redt once before by the same person, but I got sick when we were supposed to go out, and we never ended up meeting). My father and brother, who know this boy from shul, speak very highly of him and tell me that he is exactly like what I’m looking for.