Photo Credit: Jewish Press

Dear Dating Coach,

I have taken your advice and I do my best to put myself into situations where I might meet my potential zivug. I go to Friday night meals, dating events, and community parties hoping to meet a special girl. There have been a number of times, however, when I was interested in someone, but just could not muster up the courage to do anything about it. I would definitely not introduce myself over the Shabbos table and I could not even bring myself to ask my host about the girl later. What if she isn’t interested? What if she says no and I am humiliated? I keep encountering potentially interesting girls but I never follow through. What’s a shy guy to do?


Scared Single


Dear Scared,

I love overnight camp. I do not love packing lists. Rows of endless obscure requirements that your child might need to get through the summer. Bug spray? Ok. That one might make sense. Flip flops? Ok. That one makes sense too. The point is, that list is long! One year, the list required a specific type of sleeping bag. Uber-specific. Who knew that sleeping bags had endless options in length, width, weight, and dream direction? (That last one might not be true.) We searched and searched (we went to Target – but we gave it our all) and did not find the right sleeping bag. Refusing to give up, we went to a camping store located many miles away. We drove for hours (62 minutes) and arrived with intent and determination. The store had the sleeping bag we needed, and we were not walking away until it was ours. Except, the store was closed. Not until 12 noon, or until tomorrow. It was closed, as in shuttered, for good. So, we went home sans sleeping bag.

(Of course, this reminds us all of the saying, “a sleeping bag in hand is better than sleeping in the bush.” I think I got that right…)



I appreciate your willingness to meet new people by attending events and local meals. I sympathize with the strength it takes for you to push yourself out of your comfort zone. You are doing your best to meet new girls and you are, but you are having trouble with following through. Your anxiety over their potential lack of interest stops you from reaching out. It feels bad to hear a “no,” so you let the fear hold you back. Nobody wants to be “rejected.”



In shidduchim, the potential for rejection exists for everyone. Those we want to date, those we ask to date, and those we are dating, all have the opportunity to say “no” should they choose to. To refuse to participate in this process because other daters might not want to meet us or date us prevents even the potential for a connection. An unwillingness to try definitely offers a negative result.



Instead, consider the worst-case scenario. They say “no.” Even worse, perhaps they are shocked that you even asked, and offer an emphatic refusal to your request to get to know them better. While you may now have learned something negative about them at this point, YOU are in the same place you were before asking: not dating them. Sure, perhaps you are slightly bruised and hurt by their lack of interest, but you were not dating them before and you are still not dating them now. Door closed, shuttered despite your effort.



They might, however, say “yes,” and then YOU would be in a different position than you were when you started. The courage to reach out directly, through a friend, a shadchan, or your host, offers you the gift of POTENTIAL. Not trying at all offers you nothing. So, take a deep breath, promise yourself a reward for your efforts, and reach out. The door might be closed; it also might be open.


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Henni Halberstam is a Dating and Marriage Coach whose expert advice will help you navigate dating and relationships in order to ensure a successful marriage. You can contact her at to schedule a phone session.