Photo Credit: Jewish Press

Dear Dating Coach,

I have a single older sister who is much more modern in her frumkeit than our family. Over time, for a variety of reasons, she has decided that our lifestyle no longer works for her, and she looks and acts differently than the way that we have been raised. She is dating guys that she meets on her own and we remain close. Newly home from a typical frum seminary however, I am terrified that she will hurt my chances in shidduchim. I love her, but I truly believe that mothers of boys and shadchanim will be less interested in me for their sons because of her. Do I still stand a chance?


Sister’s Shadow


Dear Shadow,

If you have a sensitive stomach, stop reading this now. For those iron-bellied brave ones – take a deep breath and dive right in. We once went to a restaurant with a bunch of family members. (We should probably have a moment of silence here…because who remembers going to restaurants at this point of Covid?) We ordered our meals, everyone was chatting and having a wonderful time. Someone in our party (totally classified), ordered soup and it arrived with steam pillowing beautifully to the table. She (or he!) lifted their spoon is anticipation and to their absolute horror, there was a long black hair doing the backstroke through the bowl. There was gagging. A lot of gagging. The soup was not eaten, dinner was disrupted, and a refusal to ever eat there again was pronounced with conviction at the table. (Who knew soup could be so dramatic?) Since that fateful meal, we have eaten there many, many times only to be offered delicious, spotless, creative dishes that we ate without hesitation. That family member however, has never eaten there again and still shudders when the word “soup” is mentioned. (No, she doesn’t actually shudder. I couldn’t help myself.)



It’s so exciting to be at the beginning of the dating process with opportunity and potential matches waiting to be made. You are now a woman, who has given thought and conviction to her future, and you are ready to meet someone who will compliment those goals and dreams. Your sister is navigating a different path, and while your love for one another can’t be contested, you worry that your community will judge you by the choices she has made. You wonder if they will question the chinuch in your home, and paint you all with one definitive brushstroke.



You are correct that there may be those who may not be interested in you because your family isn’t Instagram perfect. There may be parents of sons and shadchanim who refuse to consider you as a potential match because of false assumptions or an unwillingness to consider any girl that doesn’t come in a perfectly presented package. Their selection process may also exclude daughters of divorced parents, daughters raised in the wrong income bracket, daughters not from their neighborhood, and daughters from subpar schools. Perhaps you could argue that this limits their choices, and perhaps it does not. Regardless, they are entitled to their choices and their judgmental arbitrary selection process, and you can’t stop them.



That being said, there are many wonderful parents and shadchanim who are not looking for perfect packages, but perfect matches. This means that they look at every girl and boy as an individual first, and then they do their homework from there. This does not make them open-minded or forgiving – this does not mean that they are overlooking “flaws” and have a willingness to settle. This means that they are hoping to win the ultimate prize – their child’s bashert, wrapped in mentchlichkeit, warmth, and kindness; just the way they always dreamed of. One tiny hair out of place in your family will not hurt your chances of finding your match. It will only hold back those patrons who never belonged in your future from the start.

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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.