Photo Credit: Jewish Press

Dear Dating coach,

A guy was suggested to me by a bunch of people. Apparently, they think we are a “perfect” match. They have all said that they think this would be a “great idea.” He sounds great by all accounts – smart, kind, driven, and fun. These are all traits that appeal to me and it does sound really promising. There is just one problem. I knew his sister growing up and she was awful. I just can’t process dating and potentially marrying this girl’s brother. She would be family, forever in my life – and the thought alone makes me cringe. Do I just pass?


Family Matters


Dear Matters,

Growing up my parents drove an Oldsmobile custom cruiser. (Don’t be jealous. We are just cool people.) It had a middle row of seats and the trunk had two seats facing the rear that could be stored when you didn’t need them. When we traveled on long road trips the seats were assigned by sibling hierarchy and by practicality. The coveted seats were up front. (Never got those.) Second best were the seats facing backwards for those with iron stomachs. (Never got those.) The worst seat was in the middle. Not only did you get that hump by your feet, but our car had a piece of the metal stitching poking out in that very spot. Every bump in the road offered you a poke and a pinch as you swayed from left to right, book-ended by the siblings on either side of you keeping you upright. Drive, pinch, drive, poke, drive pinch…you get the bruises..gist. (THAT – was always my seat.)

I didn’t choose the middle seat – but that bit of soreness always felt like a minor inconvenience when we got to our wonderful final destination.


You Don’t Have…

It is usually a good feeling to have someone suggested to you that seems like a great match. It bolsters us to hear that more than one or two people believe you would connect. This is especially true when everything else we learn, as far as character, personality, and middos feel right as well. Yet, you are struggling with one such match because you are familiar with his sister. You do not have fond memories of your interactions. Moreover, you can’t shake the association that they have with one another and the even more glaring possibility that you could one day be family with someone you believe is “awful.” You are ready to walk away.


To Be Perfect…

In a perfect world, on a perfect day, it would be perfect to marry someone perfect who has the perfect family. You would all get along perfectly and have perfect interactions and go on perfect family outings. You would love his perfect sisters and your perfect in-laws, and they would of course think you are perfect as well.


For Someone.

Realistically speaking though, this is unlikely. Yes, it’s true that when you marry someone their family becomes a big part of your life as well. Still, it is unrealistic and impractical to make this a strong requirement in selecting a future spouse. It is always easier and highly encouraged to have a nice relationship with your spouse’s family, but to dismiss a potential match because you didn’t like his sibling is self-sabotage. (Consider also the possibility that she has grown in her character and kindness.) I would also hope that if you would be blessed to connect and marry this person, and his sister has not changed – you would still try your best to have a cordial and respectful relationship.

Remember, we are looking for a spouse. A lovely family is an added bonus, but not a requirement as long as you both create your OWN family that is united and on the same page. The goal, is always to make that journey together, even with some minor pokes – the destination is definitely worth it.


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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.