I am a 36-year-old guy caught in an unusual dilemma. For the past few weeks, I have been going out with a girl who is 29. We get along OK, as she is very nice and personable. She comes from an amazing family. Her parents are great, and her older sister is very special.

The sister I am talking about is 38. Every time I go over to the house, we seem to have a special connection. At first I thought it was my imagination, because she is very pretty. But I found out through friends that the older sister is expressing the same feelings.

I haven’t told anyone else that I am thinking of finding a way to date the older sister. I’m scared that people will think I’m weird, or worse. What is the best approach I can take in such a situation where everyone will be happy in the end?


By Baila Sebrow

For starters, there exists no sticky situation where everyone will entirely be happy in the end. You can be sure that, in addition to the expected tongue-wagging amongst friends and strangers alike, there will likely also be tears and heartache for the girl you are dating, and perhaps even for you. Before you seek an amicable resolution, you need to examine the situation from its foundation.

At age 36, you have been dating a girl who is seven years your junior. From the expected viewpoint of society, a relationship of this kind would make you the envy of guys who are in your similar unmarried state. That said, you seem ready to renounce that so-called prestige in shidduch dating for philosophical reasons.

Dating the sister who is two years your senior feels right to you. You convey sincerity and I trust that your intentions are honorable. My concern, however, lies with the conscious or possibly subconscious motives of the older sister. I do not doubt that the older sister is a nice person. But human nature equips us with emotions, and when triggered can manifest strongly.

You need to be cognizant that as difficult as it is for a guy to be unmarried into his thirties, you cannot imagine the pain, grief, and shame experienced by girls in that age bracket. Adding salt to an already deep wound is when the younger sister of a girl in her upper thirties begins to date, even with her verbal permission and approval. Watching the younger going out with a guy closer to her own age realistically stands to fuel a girl’s humiliation.

I am not questioning the opinion of the older sister expressing to others that she senses a special connection with you. She likely does share the same sentiments as you. And if so, the questions you need to ask yourself are What is she feeling? and Why is she feeling that way?

The concern that needs to be addressed is whether she shares the same basis as you in terms of sensing a sincere shidduch commonality. Or are her reasons for that connection a consequence of both of you being in the same league, agewise?

Furthermore, is the connection she perceives a result of intellectual commonality? If that is the case, it would be normal for her to feel that she and you are more plausible for dating than her younger sister. The fact that she told other people of her feelings is indicative that she meant for you to find out.

Put the older sister’s reasons aside for one moment and focus on the relationship with the girl you are currently dating. You state that you get along “OK” with her. That is a very vanilla description of someone whom you have been seeing for the past few weeks, and whose family you have gotten to know well. You loudly sing the praises of everyone in her family, except this 29-year-old girl you are currently dating.

I appreciate your dignified manner in not revealing to anyone the details of your circumstances. You demonstrate maturity and sensitivity. I will advise you that except for a trusted member of your family, please continue to not say anything yet.

Even if her older sister would not be in the picture, I would recommend that based on your lukewarm feelings for the girl you are dating, it would be best to reevaluate your relationship with her. After assessing the relationship with the girl you are dating, if you feel that you cannot imagine a matrimonial future with her, then it would be best for you to terminate the relationship. Be careful that your motives have zero to do with the older sister. For your own future happiness, this needs to be examined objectively.

If your decision is such that you wish to continue dating her, be wise and make no mention of any interest in her older sister, even from a platonic perspective. These things have the potential of getting interpreted very badly and can get blown out of proportion. So for the sake of all concerned, it is best to let it be.

On the other hand, if after much introspection you determine that the girl you are dating is not right for you, and the relationship ends, make it a strong point by verbalizing that this was a decision based on compatibility issues only.

Provided that you will not be in a relationship anymore, and having given yourself time to mend, as everyone needs such a period, regardless of who chose to break up, you may then ask someone of respected authority such as a rav to intervene in suggesting you as a potential match for the older sister.

How things will play out within the family dynamics in the future remains to be seen. There have been situations similar to what you experienced where a guy dated one sister and later married another sister. But each case is different, as are the personalities of the people involved. May your instincts guide you wisely.

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis. She can be reached at v

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