Photo Credit: Jewish Press

Dear Dating Coach,

I just told my parents that I will come home for the “first days” of Sukkos, but not the “second days” – and they flipped out! Being around my siblings (including my younger sister and her two kids!) for the entire Yom Tov is just too hard for me. Plus, I feel compelled to help my parents the most since I am single and “free,” so I end up resenting my siblings even more by the time Yom Tov is over. I’m just not interested in spending the entire Sukkos with all of them. So why the guilt trip?!


Irritated and Independent


Dear Independent,

Sometimes, I feel like I need to call in reinforcements. I could really use the captain of the debate team, a fashion designer, a fisherman, and a cheerleader all at once. The task: convince my toddler to put on the outfit that I have carefully laid out. Arguments must be made with finesse, trends must be explained (perhaps a vision board?), a firm hold must be established (no matter how wiggly the subject), all as a synchronized and choreographed cheer is performed. This seems to be the only hope for success (and realistically, even with all that, the odds are 70/30, and not in my favor.)

So even if the outfit my child picks isn’t to my style (or anyone’s style), and her take on “matching” defies convention, if in the end she is dressed and satisfied, that counts for a lot. We save our “elite team” for the important things (“No sweetie, you can’t wear a bathing suit to my sister’s wedding”) and loosen the reins at other times – because self-worth and independence are invaluable.



You’re tired, and I get it. Tired of being the single sibling, tired of helping the most, and tired of everyone treating you like you can’t possibly be OK on your own. You tried to establish a boundary that you felt was fair to your family and comfortable for you. Still, your parents were hurt, and perhaps scared of what others would think about their single daughter not spending the entire Yom Tov with them. They also love you and worry about you, and your being home offers them some measure of control as you go through the shidduch process (a process that is often beyond their control).

I’m sure you enjoy being with your siblings, their spouses, and your nieces and nephews, but that doesn’t negate the feelings of sadness and pain that being with them brings to light as you daven for your own spouse and your own family. Finally, you are an independent woman who is completely self-sufficient the rest of the year. You have an active life filled with friends, work, and the new community that you are a part of. You know that you will be fine for part of Yom Tov on your own turf, and you wonder why your parents can’t accept that.



You’ve established your independence and created a solid foundation. Now, it’s time to further cement this growth by capping it with clear and careful communication. Tell your parents that you love them and that you value your time on Yom Tov with them and the rest of your family. Tell them that at this point in your life, you would prefer to spend the second half of Yom Tov with friends who are in a similar “single” position. Tell them about the collaborative Yom Tov “potlucks” you’ve planned, and about the meals that you have been invited to join that will be filled with singles and friends. Make it clear that while you will not be with them, you will not be alone.

Then use the time over the second days of Yom Tov to attend singles’ Sukkos events, and make an effort to meet new potential matches at the meals that you have been invited to. Use this time wisely, so that you can be one step closer to happily joining your family for the entire Yom Tov with your own family very soon.


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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.