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Dear Dating Coach,

I am 22 and I have two older single sisters. I always thought that they would get married and then it would be my turn. But they are both still single and I just didn’t want to wait anymore. We have discussed my dating and both were not opposed in any way, but I don’t think they really took me seriously. A few months ago, a friend suggested her brother as a possible shidduch for me and we started dating. We progressed quickly, and we are ready to get engaged. I have discussed this with my parents and while they were at first very taken aback, they are now on board. I meant to tell my sisters as well, but kept pushing it off. I need advice! I don’t want them to be upset!


Stealth Sister


Dear Sister,

We went to a wedding this week and it was magical. The bride worried about rain. Summer in Florida and rain are often synonymous so it was a definite possibility. The week before the wedding we watched the forecast carefully. One day it poured so heavily that the streets flooded. The next day, the sky was a brilliant blue with nary a cloud to be found. The weather roller coaster continued prompting a “will it, won’t it” poll in my neighborhood. I’m no meteorologist, but I was positive in my weather prediction: It would rain or it wouldn’t. (Follow me for more pro weather tips at @RainOrShineOrWhatevs. Actually, don’t, because that’s fake.)

What an exciting and stressful time for you! You decided to take some control of a situation that felt very much out of your control and were met with success. You were introduced to someone that you connected with quickly and easily and now you are ready to get engaged. While this would typically be only a joyful event, it is now tempered with anxiety as you worry about your sisters and how they will react. You don’t want to hurt them, and you are concerned that they will not only be surprised but hurt and upset by your subterfuge and your unwillingness to “wait your turn.”

Take a breath. You are going to get engaged to someone who makes you very happy and that is a huge bracha. We can perhaps discuss the importance of honesty. You did not give your sisters the chance to accept your choice with dignity before you began dating. You may argue that you worried that they would react poorly, but now they will certainly feel blindsided and hurt by your deception. You are nearing the finish line, however, with your choices made. You can only move forward.

Sit down with your sisters and tell them the truth. Speak respectfully and apologize for not being more transparent with your feelings and your intentions. Ask for their forgiveness for your artifice and for “skipping the line.” Allow them to respond. They may surprise you with immediate acceptance and understanding, or they might be very angry with you. They are allowed to feel what they feel. Accept their reactions with humility. Do your best to give them the space they need to process and then do what you can to repair any schisms this may create in the bond that you share. You made a choice and G-d willing everyone will share in your joy. If that does not happen immediately, accept what you cannot control. Instead, appreciate the mazel that you have been given, and do everything in your power to honor your relationship with your precious sisters.


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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.