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

1 Feeling Bitter

Question: Hi, Debbie! Basically, I’m 22 and have never even gone out once… But that’s not what I’d like to ask about! My issue is as follows: as I get older and more and more girls and boys younger than me are getting engaged, I find my resentment growing. Every time I hear of someone… Read More »

0 Cold Feet?

Hi Debbie, I have a unique situation (at least I think so). I have gone out with a few boys but on many dates. You see, two of the boys I went out with, the dating became fairly serious. Both times, everything was going pretty smoothly and I thought I liked the boy but when… Read More »

0 Being Pulled In Two Directions

Question: B”H I must preface this letter by saying that Hashem is really watching over me, and I am not having that hard of a time in shidduchim. I have not yet been zoche to find my zivug, but at the same time, I don’t have the horror stories that some girls have in dealing… Read More »

3 Why Isn’t He Calling The Shadchan?

Dear Debbie, I recently dated a boy and was very bothered by the length of time it took for him to get back to the Shadchan.  He had come in from out of town, and before the date we had mentioned that if it went well, maybe we’d go out again while he was still… Read More »

0 Staying Connected

Question: I’m 21 & I have an older sister. We’re very open with the whole dating thing but obviously I do not want to get married before my sister. I feel like it would hurt all of us – my parents, my sister, & I. Whats bothering me is that I used to pray with… Read More »