Author Archives: Debbie

About Debbie

Debbie Shapiro is a wife, mother, grandmother (in that order), and a resident of Jerusalem for over 40 years. In addition to her work as a writer and PR director, she enjoys playing with her grandchildren, being there for her children, and writing for columns like this one! She's made quite a few shidduchim and is known for her common sense. She welcomes questions, comments, feedback and interaction. Check out Debbie’s latest book here

0 I Said No But…


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 felt important. I felt like I was dominating the relationship- I am loud and talkative. This made me feel like I was better than him (though I know its not true! Maybe it made me not be able to respect him because he wasn’t as funny or loud etc? I don’t know if I care that my husband is louder than me because I know I’m very loud but I want to be able to look up to him in some way.)

Another thing that made me a bit uncomfortable was how candid he was about his feelings. I know thats a good thing but I think my family is not like that and it made him seem more feminine.
He was from a more modern background and frummed out while my family is more modern orthodox and I followed my older sister to the right and would consider myself yeshivish (I want a husband who learns and wears black and white, want to send my kids to bais yaakov etc- more I feel like thats the only way to survive in this crazy world and I identify with the hashkafa though because of my background I am more out there and “up to date”.) When he frummed out he got into the “chassidus” and has brisker payis and likes certain things about the chassidish lifestyle which is so not my thing. He is learning in a yeshiva and would consider himself yeshivish but he has that chassidish team.

Also, not because he is yeshivish but in general it seems that his family does not value education which is something my family, and I too, am big on. I think it is important to be intellectually curious and he did not, he was all for just getting by with whatever grades and don’t need to give schoolwork your all. Also, I am not a genius but I work hard at school and am iyH going for pharmacy. I couldn’t tell if he was smart also- he was in the top shiur but said he does a lot on his own and doesn’t love style of learning in shiur so much- doesn’t really work for him.(I don’t know so much about boys and yeshiva but this seems weird to me.)

I said no for these reasons but didn’t really tell him more than- I think we are on different pages hashkafically (I spoke with someone who said it sounds like he needs someone who appreciates the chassidish leanings and I don’t so that was my concrete basis…).

I still think about him a lot and miss the friendship we had and the chemistry that was good between us from the beginning. I think in general I am the type of person that would love having a boyfriend but never did because I did not think it was acceptable before marriage so I don’t know if that plays a factor. I had one date before this guy and one date after that were both not at all shayach. I don’t know if what I am feeling is normal and if my thoughts about him will go away if I date someone else also shayach even somewhat. When friends talk about dating stories I basically just have what to talk about from dates with this boy which were all really positive experiences. I still think these reasons make sense but I want to make sure that I am not holding on to things I should let go of and I just also want encouragement about these reasons being valid and legitimate(I guess you can tell I am really inexperienced) and that I shouldn’t revisit this.
Thanks so much!



Dear not sure,
It sounds like you have decided already that this boy is not for you. ​It’s normal to have all kinds of doubts and emotions, and yes, chemistry does play an important part in cementing a relationship.
It would be helpful to make a list of things that are really important to you (generally a quiet spouse is a plus if you’re loud and talkative — opposites complete each other), and then go from there. But remember, chitzoniyus is just that, and it’s the inner part you are looking for. And then, never say never — I always defined myself as Yeshiva-litvishe, and in the end, I married a chassid, and I can tell you that he really is perfect for me!
And if, after a few more weeks you are still thinking about this guy, then try it out again.
 And please accept my apologies for not getting back to you earlier. I wasn’t well, and couldn’t really get to my emails.

0 Getting A Yes While Dating?


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 a match. Of course that is why we will go out.
As soon as we gave a yes we got a call from a second shadchan that another boy is looking into us and likes what they hear so far, but would like us to make an inquiry or 2, just to see if we are in the right ballpark, before the make further inquiries.
We are afraid to tell them that we are about to begin something else. They will move on and likely never come back, and the first boy might not go past a first date.
Is there a way for us to stall the 2nd boy until after I meet the first, just to get a clearer picture? Or should I be honest but risk losing it?
Thanks for your help.


Wow, isn’t that wonderful! When it rains, it pours. Interesting enough, this is what happened to many of my children; there were no suggestions, nothing was moving, and then, suddenly many at once — which always ended in a mazel tov!

Although I am very against playing in two fields at once, I don’t think there is anything wrong in having your parents, or someone else you trust, look into it, but without them involving you, and of course, we’re talking about very basic inquiries. At least until after the first date. And once the other person is making some inquiries, forget about it completely.


Q. ON A.:

Thanks for your reply.
If I understand correctly, my parents can make an inquiry or two about the second boy, and get back to the 2nd shadchan that there is possibility. The 2nd boy can look into me even though I have a first date set up with the first boy. Should they get back with a yes, and I am continuing with the first boy (at least to a second date) I can tell them then that right now I am busy.
Just clarifying your advice.
Thanks so much.


On second thought, if there is any way to stall giving an answer to the parents of the second boy, saying something like, We’ll have an answer within the next week, that would be better. But otherwise, yes, let your parents check and you should just forget about it.

Q. On A.

I went out twice with boy #1. It was ok, I have certain reservations, but am willing to try a 3rd time. The boy got back to the shadchan that he is willing to try a 3rd time but his gut feeling is that this is not for him.
My question is what to do now with boy #2. My parents really must get back to them already, should we be upfront with them that I am busy, but right now it seems that boy #1 has one foot out the door. To give up the 2nd shidduch doesn’t seem to make sense at this point. But I don’t feel its right to not go out a 3rd time with the first boy because you never know. So not sure what to do.

0 Opening Up


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 I’m ready to take things further?
Also, I know that he trusts me because he revealed a lot of personal information about himself and I saw him constantly observing me for my reaction, which I guess he was ok with because he wanted to go out again. I don’t think that I have been that forthcoming with my struggles as he has been with me. How can I build my trust in him and show him that I trust him?
I don’t mean to rush you, Debbie, but I would appreciate a prompt response, just like your previous advice, which was very helpful. We will probably go out again very soon and I’d like to be prepared. My parents have been very supportive but I’m looking for a more experienced and objective perspective.
Thank you so much!


Again, it’s hard to respond when I don’t know you personally. Dating is a very unnatural situation, because on one hand we are expected to slowly reveal our neshama to the person we’re dating,  yet, we are very aware that he is evaluating us, just as we are evaluating him, and that the relationship might end at any time. When we open ourselves up, we are making ourselves vulnerable, and more open to pain. Obviously, that makes it more difficult to “be real” on a date.
That’s why it’s often easier for people to open up to a total stranger. When people  open up to  a date, or even to a spouse or close friends, they are assuming a certain level of trust, and if that trust is broken or used as ammunition in an argument (of course you did this, after all….) the pain is even greater.  If you’ve been in a situation where someone broke your trust, or took advantage of your vulnerability (all that back stabbing in school!) then it will be even harder to allow yourself to be vulnerable.
My suggestion — be honest. Tell your date that you really appreciate how he’s opened up to you, and that you feel close to him, but that it’s difficult for you to open up to him because you cannot know where the relationship is going. That you are afraid of being hurt.
then take it from there.
Much hatzlacha, and please let me know how it goes.

2 What Should I Do Now?


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 out about this and mentioned something to me…basically that my parents did the wrong thing. What do you suggest I do? I agree with this person but I can’t make my parents comfortable with something when they are not. I also do not want to pressure my parents or cause any strife. Please guide me. Thank you very much


I am really impressed with your sensitivity and kibud horim. There is a lucky bachur out there, waiting for you!

My immediate reaction here is SPEAK TO A RAV. It’s very possible that the boy’s side spoke to this respectable person and requested that he talk to you, in which case he has the boy’s benefit in mind. You need a rav that knows you, and knows your parents. If the rav feels that there is what to discuss, he’ll speak with your parents. It’s important to have their backing and blessings, both for the shidduch stage, as well as for a good marriage. And if the rav decides that your parents are right in refusing this shidduch, then “ein simcha k’hataros sefeikot” and you are one step closer to finding your beshert.

Hoping to hear good news,


1 College Because He Wants It Or Not?


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 may as well do it now and not later.) The last time I dated a boy with a degree, I was told his parents insisted on the degree but that he wanted to learn, and would learn for a while. On our fourth date, I found out he believed that boy has to earn the real money and he wasn’t planning on learning very long. I was very upset that it took so long for me know that and I really don’t want that to happen again. We did research and everyone seemed to think he was a learner, including the shadchan. So we said yes. When my brother heard I was going to date him, he said “He’s so not for you, he’s not going to learn a long time”> So how do I find out why he’s in college, and how soon can I do it? Everyone always says talk about light things on the first date. Can you think of a light, non judgmental way for me to ask him what his plans are regarding college and working, already on the first date?


How about just asking him outright, “What are you majoring in in college?” and then take it from there. Be interested in HIM. Does he enjoy his studies? Is there something that really “speaks” to him? Maybe he’s studying education, so that he’ll have the right credentials if he decides to eventually go into chinuch. Or perhaps his parents insist that he get a BA, and he’s taking the minimum requirements just to be m’chabed them. I’m sure that if he doesn’t feel that he is being pinned to the wall, he’ll feel comfortable sharing some of his dreams and aspirations with you!

Lots of luck!