Photo Credit: Jewish Press

Dear Dating Coach,

I have known my best friend since we were in kindergarten. She is incredibly important to me and a huge part of my life. She has a few older brothers who went to yeshiva out of town and so I rarely saw them. Two of them recently got married, and the brother just above her has started to date. A few people have suggested him to my parents as a potential match for me. In truth, it sounds like we have a lot in common and I obviously already love his sister and his family. I just feel really weird and nervous about the whole thing. If we go out and it works, I would be the luckiest girl in the world. I would have a wonderful husband and the best sister-in-law who I already adore. At the same time, if this doesn’t work, I am worried it will jeopardize my precious friendship and things will never be the same. We need to give them an answer. Please help!




Dear BFF,

I recently read an article about a tennis player who visualizes every big match he plays before it happens. He imagines himself on game day in his tennis whites, he sees the net pulled tight, and he envisions his serve and the sound it makes as it flies over the net. Swoosh! He sees his opponent as he lines up his shot and every shot thereafter, visualizing the game in its entirety before he ever steps onto the court. When the time comes for him to play, he feels prepared, having already pictured every scenario; his goal set and clear in his mind. Does he win every time? No. Does he win most of the time? Yes.

Your question is complicated. We cannot discount that you are proposing to take a big risk. This friend is very dear to you. You have years and years of trust and connection, that we would be foolish to discount. It is true that if you date your friend’s brother and it doesn’t work, even with care and respect, it is unlikely that your friendship would be unaffected. He is her brother, her family, and as much as she loves you, there is great potential for awkwardness at the very least, and even a ruined friendship.


Tracht Gut Vet Zein Gut

That being said, the potential reward should this work is massive. A family you admire, a friend you adore, and someone that you can be assured was raised similarly to the friend that means so much to you. There are no secrets about his family. No unknowns about his hashkafa, or their values. You know how their family functions and you are not only comfortable with them, but a part of them in many ways already. If this does work, your transition into married life with his family would not only be easy, it would feel like a tremendous gift.

Speak to your friend and then take the leap. Do your best to set the tone for your ongoing friendship regardless of what may be, but with the understanding that you will accept any repercussions as well. Then visualize this dating journey and see the happiness and blessing that can be yours. Plan for good and a joyful connection and when you do go out, do your best to focus on the positivity and connection that might be waiting for you. Of course, you need to date with logic and a clear head, but you can absolutely envision the happy outcome that you are all hoping for. We only benefit from dating with positive intention. So go for it and remember, no risk, no reward.

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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.