Photo Credit: Jewish Press

Dear Dating Coach,

I dated a great girl for a while, but I ultimately felt the need to walk away because I thought my feeling weren’t strong enough. Since then, I have dated several other girls who all never measured up in my mind to her. I compared them all to our experience and connection and while they were all great, they were not “her.” The shadchan who set us up originally reached out to me yesterday asking if I would consider dating her again. She said that the girl has not liked anyone she has dated as much as me and has always felt like I could have been “the one.” I am really tempted to go for a second chance, but I am worried that I could really hurt her. What if my feelings don’t grow again and this doesn’t work out? I would feel terrible! I already hurt her once, how could I take a chance to hurt her twice? What should I do? Try or walk away?


Gun Shy


Dear Shy,

What is up with baking? Why does it have to be so hard? I read the recipe until my eyes glaze over. I line up my measuring spoons and cups like good little culinary soldiers. I measure just so. I sift, whisk, temper, and kneed. I set a timer for my mixer and let the eggs come to room temperature with classical music to relax them. When the batter is ready, I allow it to enter a perfectly regulated oven under optimum temperature conditions, and only on the baking rack situated for success. I talk to the cake, offering it love and encouragement. “You’ve got this chocolate cake, you are the bundt!” Then, at exactly 42 minutes and 15 and a half seconds I carefully remove the cake in silent meditation and let it rest peacefully. Finally, I gently remove it from the cake pan, and boom! A big cake mess! All. The. Time! Baking! I try to control the process, but man bakes and cakes laugh.


Strawberry Short Cake

Thank you for your letter. You feel like you have a weight on your shoulders. You dated someone once that you really liked, but could not fully commit to. Now, with the passage of time and reflection, you both might be interested in testing your connection again. However, you feel a responsibility for her feelings since you ended things initially and worry that the same thing could happen again. So, while you hope to make it to an engagement and plan to commit to the process completely, you still worry about the risk that you could cause her pain again. Is it worth taking a chance, or should you walk away for good?


Lemon Meringue

Your respect for her feelings is admirable. You don’t want to hurt her. This shows character and kindness and you should be commended for it. But, while I applaud your concern for what she might feel, I also feel compelled to let you know that you are not the ‘King of Feelings’ and therefore don’t get to decide if other people get to take a chance with theirs. Any healthy person must be aware that dating poses a risk to our feelings. Someone may not like us, may not connect with us, or decide to stop dating us when we are not ready to let go. Even when things are going well, we may have bruised feelings when we feel a stronger connection earlier that the person we are dating or feel “ready” before they do. We are all responsible for our own feelings. We get to decide on the risks we take with them.



If all goes smoothly, you can both find yourselves under a chuppah with feelings of great joy. If all does not go smoothly, there may be feelings of sadness. This is a chance every person must take willingly and an absolutely personal choice. You can prepare and execute with precision, and still things may not work out as well as you hope. We can only control so much. Still, we are all praying that your feelings align just so, perfectly baked, and you live happily ever after, the end.


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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 [email protected] to schedule a phone session.