Question: My son will begin shidduchim soon, having returned from learning in Eretz Yisroel this past Sukkos. My son has many maalos and we’ve been fortunate to be redd many shidduchim. I have a stack of résumés on my kitchen table. I am not saying this to boast. I am mentioning it because, as strange...Read More

Question: When redding a shidduch, it is my preference to speak directly with each single as the shidduch moves along. Of course, I am always happy to speak with the parents as well, but I feel it is important to speak with the single themselves after each date to be sure that I am hearing...Read More

Question: I was recently asked to redd a shidduch to a boy of mediocre intellectual ability who insists that he needs a girl of pleasant appearance “with a degree.” He says that he wants to learn for three years and go to medical school or pursue a professional career.  I certainly don’t want to burst his bubble, but how do I...Read More

Question: I am involved in a shidduch where the couple has met five times.  The dates are going well, and the conversation seems to flow naturally, but the couple has not yet connected on an emotional level. What pointers can I give the boy–or the girl– to take it to the next level?  Answer: Creating and sustaining an emotional...Read More

Question: My sister is currently an “older single.” She is a wonderful girl with “alle maalos” and she continues to get dates and go out. However, I find there to be an increasingly frustrating and hurtful trend of certain boys, specifically “older” ones, ending shidduchim after a first date. It is so hurtful to the girl and deeply...Read More

Question: After my wife passed away a number of years ago, a second marriage was not on mind. Recently, though, I have been redd a number of shidduchim and I am ready to consider it. However, my fifteen-year-old daughter has told me in no uncertain terms that she does not want me to get re-married....Read More

Question: Unlike most yeshiva bochurim these days, I own my own car. It is a 1997 Mazda Protégé in perfect running condition. I recently went out with a girl. The next day I had found out that she had “no’d” me. She told the shadchan that I was really nice, and that she had a...Read More

Question: My son, who is approaching age 30, has been in shidduchim for quite a number of years. He learns in a yeshiva that has a dormitory. Recently, we were told by a shadchan that the parents of a girl we had given a yes to questioned why our son is still in a dorm....Read More

Question: A while ago, one of my relatives told me that she has an excellent shidduch for me. She described the boy as excellent in every way and proceeded to call the mother and give her my name. Every few weeks, she would update me on the progress – “the boy is busy now,” “the boy is...Read More

Question: My son has gone out with a girl twice. After the second date, he told me that during the course of conversation, it emerged that this girl’s sisters are married to choshuve bnei Torah who are talmidei chachomim. He is concerned that, firstly, since he is not on their caliber, this girl will look...Read More