I am 25 years old. I’m dating a girl who is 22, but I like her 28-year-old sister. A shadchan introduced me to the girl I’m dating. Her résumé seemed great, and we started dating.
I really got involved with her so that I could spend more time around her sister. Her sister is a lot of fun, and I have much more in common with her than with her younger sister.
The problem is that the older sister does not know how I really feel about her. I know she likes me. I am also sure that if I break up with her sister that she would date me.
But I have a few problems. The first is that both her parents and mine are pushing for an engagement. Also, the girl I’m dating really likes me. She is always sending me poems and baking me cookies. If I break up with this girl, how long should I wait before the older sister would feel comfortable being redt to me?
I only confided in one person about this, and my friend thinks that I should first make sure that the older sister likes me as much as I like her. And if not, then I should get engaged to the girl I’m dating.
I feel mixed up right now. What do you think I should do?
By Baila Sebrow
If this was a one-sentence answer, I would tell you that both sisters are better off without you. I apologize for sounding so harsh, but you have not mentioned once about feeling bad for anyone but yourself. Therefore, my response will be focused on the well-being of the girl you are dating. In addition, as you mentioned, there is the possibility that the older sister may like you. If so, then her happiness is at stake, too.
It is not unusual for someone to develop a “crush” on the sibling of a date. In that respect, your situation is, to some extent, run-of-the-mill. But in our frum society, these things are not discussed often, so those who feel this sort of infatuation generally tend to either continue dating the person as though nothing else is happening, or they break up.
From the way you describe your initial contact with the girl you are dating, it appears that you were not all too keen on her to begin with. Other than expressing interest in her flawless résumé, there seems to be nothing else that quite held your attention except that she has a sister that you like. So even though you were consciously aware of that fact, you stayed in the relationship, allowing it to progress. I believe you did so not only because you wanted to maintain contact with her sister, but also in order to make sure the sister would start to feel the same way about you.
From the way you describe the girl’s sister and how you feel about her, I assume you made it your business to hang around the house more than would be expected in a typical situation. Not only that, but it sounds like you have been spending an extraordinary amount of time with this older sister. I wonder how no one else, especially the girl you are dating, picked up on what is really going on right under their noses–to the extent that the poor girl you are dating still continues to bake cookies and send you poems. It is possible that her parents might have an idea, and that is why they are pushing for an engagement. Some people have the misguided notion that marriage solves all deficiencies.
I find it peculiar that the older sister actually played your game. If she was kibbitzing with you once in a while, I would venture to say that she was just being nice, trying to make you feel welcome and part of the family. However, this tale has been going on for too long. It’s possible that the older sister is oblivious to your true feelings, and that is why she is giving you the impression that she likes you. My gut feeling is that she is enjoying the attention you are generously lavishing on her.
In a normal situation, the sister should have put a stop to your shenanigans. She should have been outraged and disgusted by them. Instead, she is giving you signals that she likes you and very likely a false impression that she would date you in the future.
Being 28 and single while watching her younger sister date cannot be easy for any girl. The way things work in the shidduch system, at 28 there are fewer suggestions coming for girls. I can imagine how painful it must have been for her to see her younger sister getting serious with a guy.
I do not believe that the older sister was looking to be flirtatious with the guy her sister is dating. However, she was unquestionably flattered when you started to show an interest in her. It made her feel that a guy, and especially one who is younger, can feel an attraction for her.
It is also possible that she encouraged your advances because a part of her may have subconsciously wished that you would like her more than her sister. However, that is as far as I believe she would allow it to go.
If you break up with the girl you are dating in the hopes that her sister will jump at the opportunity to date and eventually marry you, then you might as well go back to sleep. That is a dream not likely to come true. There would be a lot at stake for the older sister to hurt her younger sister so badly. Not only would she destroy family relations, but she will be viewed as the girl who “stole her sister’s boyfriend.” In addition, all of her family, friends, and neighbors will end up disliking you, while waiting for the marriage to go sour. Do you really want to be in a relationship where everyone will hope and wish for the marriage not to last?
I know of a few cases where it has happened that a girl married the guy her sister was dating. There were no happy endings. That is because the foundation of the relationship was unhealthy.
Your friend’s advice is very poor. Wait until you know for sure that the older sister likes you, and, if not, marry the younger one? Is he serious? For heaven’s sake, you are dealing with the feelings of a human being. Put yourself in that position. Would you like it if a girl did that to you?
You are not ready to marry anyone at this point. You must first stop leading on the girl you are dating. You make it clear to everyone that you do not care for her. Marrying a girl who possesses the nurturing qualities she conveys to you will ultimately be doing her serious injustice. Feeling the way you do about her, there appears to be little chance that you can possibly reciprocate by treating her kindly as she rightfully deserves. Therefore, it would be in her best interest not to allow this relationship to advance any further. I also advise you to not bother with any attempts to have yourself redt to the older sister, lest you end up ruining your reputation altogether.
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
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