Category Archives: Ask the Shadchan

Welcome to the Ask The Shadchan section of We hope this column will be helpful to you when questions arise during the Shidduch process. Please feel free to ask any questions about dating, relationships, proper protocol or anything else that may come up.

Contact Debbie

0 I Said No But…

Question: I dated a boy for about 3 weeks last May. We went out 6 times. I really had a good time, he was a baal maale, baal middos, was considerate, nice, and cared deeply about Torah. We had really good chemistry and I liked being with him. However, he lacked certain things that I… Read More »

0 Getting A Yes While Dating?

Question: I am a 23 year old girl I have been going out for 4 years and have been having a hard time in shidduchim. Many months can go by before getting a yes from a boy. I have recently got a yes, the boy and family sound nice but the personality might be not… Read More »

0 Opening Up

Question: I’d like your advice on a shidduch I’m involved in right now. Right now, we are in between the 3rd and 4th date. He told the shadchan that he likes me and that he “sees possibilities”. I definitely like him and admire the person that he is. How do I signal to him that… Read More »

2 What Should I Do Now?

Question: Hi there, I hope you’ll be able to answer my question. There was a particular shidduch that was mentioned that my parents didn’t want. I usually agree with my parents but this time they’re uncomfortable with something that I am okay with (not hashkafic issue or anything like that). A very respectable person found… Read More »

1 College Because He Wants It Or Not?

Question: I’ve been set up with a boy who is in college and I am looking for a learning boy. I know that it is very possible for a boy to be in college and still want to sit and learn for a while. (ex: his parents insist or he is older and figures he… Read More »