Photo Credit: Jewish Press

Dear Dating Coach,

I am on cloud nine! I am engaged and counting down until my wedding day! But with this busy yom tov season, things have gotten a bit complicated. Will we be with his family? Will we be with my family? What days? Are they equal? My family goes away for Sukkos every year and I want to be with them, but his family wants us to be by them as well. I am happy to spend time with them, but don’t see why we can’t just be with my family for the whole Sukkos. I feel like a ping pong ball and we are not even married yet! Is it me or are they being unreasonable?


Single Stretched


Dear Stretched,

I am teaching my baby about compromise and it is going great! (That is not true.) When there was a recent disagreement over who got to play with a specific toy, my sweetheart readily cooperated and refused to share the toy. When offered a healthy dinner with the option of a small dessert versus a demand for candy, my darling declined dinner overall and generously fed it to the floor instead. When offered the easy choice of sitting in the stroller or walking alongside the stroller, my angel chose to run through the airport laughing hysterically. (Yes, that was us.) So, you can clearly see that my dear baby is already proficient in the art of compromise. Impressive. I know.


Why Don’t We…

Mazel tov to you! What an exciting time! You are so happy to be engaged to the right person, but feel torn between the demands of both of your families for yom tov. You naturally, want to be with yours, and he likely wants to be with his family. Together you hope to celebrate a lifetime of yomim tovim, and the thought of dealing with the tug of war of both families feels daunting. You just want to be able to spend your yom tov with whomever appeals and don’t get why that has to be a big deal.


Just Compromise…

In the course of your marriage, it is unlikely that every yom tov will be divided exactly the same between families. Perhaps you may even spend the majority of them with one side over the other. A marriage filled with checks and balances and the need for an even playing field is always a recipe for conflict and resentment. Instead, focus on compromise for the overall health and happiness of you as a couple and a family. This is less about “first days by your family and second days by my family,” and more about making sure that you and your chosson both feel like your choices and needs are seen and heard. This might mean that you are willing to have a yom tov that is less comfortable for you so that you both have a chance with your families.


And Do Things My Way…

Be careful to lay the groundwork for a marriage based on mutual respect and a willingness to compromise. This doesn’t always mean that you will get what you want in the short term, but it does mean that in the long term, you will have everything you could ever hope for.

Henni Halberstam is a Dating and Relationship 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.


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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.