By Baila Sebrow


I am dating a girl, but as crazy as it sounds, I really like her friend who always hangs out with her. Her mother, who is a shadchan, introduced me to the girl I’m dating. Her résumé seemed great, I liked her picture and everything that she said she is looking for, so it made sense for me to date her.

Her friend has issues with her parents, so she spends every Shabbos and yom tov there, and even during the week, like Sundays too. We got to know each other really well, and I like her a lot, and I think that we have more in common with each other than the girl I am dating. She is so much fun, and gets my jokes, and her sense of humor is unbelievable! I spoke to my parents about it, and they don’t think that the friend is a good idea for me because of her family situation and a few other things.

Here’s the sticky part. My parents and my girlfriend’s parents are going away to the same program for Pesach. Our parents are friends with each other. Her friend is going to be there too, because she always goes where my girlfriend’s family goes. She does not know how I really feel about her. I can tell that she likes me. I am sure that if I break up with her friend that she would date me. I also know that since we are all going to be sitting and eating together, we will get closer, and that’s going to make things even crazier for me.

The big problem is that both my girlfriend’s parents and mine are pushing for an engagement and keep hinting that I should propose during chol hamoed. The girl I’m dating is crazy about me, and in a way, I am crazy about her too. She is always sending me cute texts, and she buys me cute things. I also buy her things!

I spoke to one friend about this situation. He thinks that I should first make sure that my girlfriend’s friend likes me as much as I like her, and then if yes, I should just go for her. And if not, then I should get engaged to the girl I’m dating.

If I do break up with my girlfriend, how long should I wait before I start dating her friend? I’m so mixed up right now. What’s your advice?


My reflexive reaction is that I don’t think that either of these young ladies should be in a relationship with you because, quite frankly, you are not ready to marry anyone. You are still in the shopping mode! Nowhere in your letter do you offer one bit of sympathy for how your girlfriend would feel about your breaking up with her, and making matters even more agonizingly devastating, for the purpose of dating her friend. In my opinion, the emotional well-being of both young ladies is at stake here. If you can so callously feel the way you do, while being in a serious relationship, then anyone who gets involved with you is potentially at risk.

I don’t think you are a bad person, nor that you have bad intentions. I believe that you are caught up in misguided feelings and notions. It is not uncommon for an individual to develop a crush on someone close to the person they are dating. In general, such topics are considered distasteful, and therefore not discussed, and in frum circles these things are considered taboo. So, for anyone who feels an infatuation for another person while in a serious relationship, with an impending engagement, in most cases the couple either continues dating one another as though nothing else is happening, or they break up because tensions run high and one of them begins to pick on the other.

Had this crush of yours been suggested to you before the young lady you are dating, it is my understanding that based on what you wrote about how your family feels about her, that you likely would have declined her. You talk about your compatibility to the one you are dating, and you express feelings for her too. Although her friend is great, and you think that you have more in common with her, it might just be that you experience a certain camaraderie with her that you don’t feel with your girlfriend. Everything on paper seemed so good with your girlfriend, and you stayed on in the relationship, allowing it progress further. Though, in the back of my mind, I wonder if you continued dating her because you wanted to maintain contact with her friend and perhaps even see where that could lead.

It would have been appropriate for you to reach out for advice early on when you realized that you are developing an affection for your girlfriend’s friend. I would have advised you to spend less time in that home to see how things are evolving with your girlfriend, rather than have two women on your mind. Nonetheless, it sounds like you have been devoting an extraordinary amount of time with her friend. It’s interesting how no one in that household picked up on what is going on right under their noses. It is possible that her parents might have figured it out, and that is why they are pushing for an engagement. There are people who erroneously assume that marriage solves all problems. The assumption of your girlfriend’s parents might be that once you are married, you will no longer feel the way you do about her friend.

I want to focus a bit on this friend. Something about the part she is playing in this trio does not sit right with me. Why is she laughing at your jokes? Why is she joking with you? And for Heaven’s sake, why is she showing you how much fun she can be? I’m sorry to say, but even if she is not interested in you in a romantic way, her behavior leaves much to be desired. She is friends with your girlfriend. Her parents treat her like their own child, from what you are saying. Should we assume that she is just being nice in trying to make you feel welcome and part of the family? Should we give her the benefit of the doubt and say that she is oblivious to your true feelings, and that is why she is behaving the way she does around you? Whatever is really going on in her head, I have a hunch that she is enjoying the attention you are heaping on her.

In a healthy typical situation, as soon as you got overly sociable with her, the friend should have put a stop to the charms you were putting on her. She should have been outraged and disgusted by it. Instead, she is continually giving you the go-ahead that she appreciates you and even possibly the (false) impression that she would date you in the future.

Whatever is going on that friend’s life, one thing we know for sure is that she sadly has a dysfunctional home life. Spending Shabbosim, yomim tovim, and other significant days in your girlfriend’s home while lacking such warmth from her own family, in addition to seeing that your girlfriend is in a relationship, I am certain there is jealousy there. It is likely that dates are not coming easily for her, and it must be painful for her to see how her friend has so much going for her while she is enduring her own challenging journey in life.

I do not believe that she was looking to be flirtatious with the guy her friend is dating. However, she was likely flattered that a guy like you, who also is in a relationship with a girl like her friend, is giving her some attention and showing an interest in her and is attracted enough to her. It probably gave her hope of some sort that she never had before. It is also possible that she encouraged your moves because a part of her may have subconsciously wished that you would like her more.

If you plan to break up with the young lady you are dating in the hopes that her friend will use that opportunity to date and eventually marry you, don’t do it! She would be taking a huge risk that if things don’t work out, she will lose the only surrogate family and generous friend that she has right now. There is much at stake for her to lose if she would take the chance to hurt her friend so terribly. She would also damage her reputation in that she will be known as the girl who stole her friend’s boyfriend. As far as you are concerned, you will be destroying family relations, and, quite frankly, not too many people will like you. If in the end you don’t marry the friend of your girlfriend, you will have ruined your name, and if you do marry her, you won’t get too many blessings from people for a successful marriage.

I know of several cases where it has happened that a young lady married the guy her friend was dating. Unfortunately, the marriages were not successful, likely because those relationships were initially built on unnatural foundations.

I am shaken by the advice your friend has given you. For him to encourage you to pursue your girlfriend’s friend to see if her feelings are mutual before breaking up is egregiously wrong. Who dares to advise that way? Both of you should put yourself in the position of your girlfriend. Would you like it if someone did that to you?

As I intimated earlier, you are not ready to marry anyone at this point. You are right that this is a sticky situation. Everyone involved, including this friend, will be spending Pesach together. This could end up in a fiasco unless you grab the bull by the horns immediately. You must put a stop to kibbitzing around with this young lady. My advice is to act nothing more than polite to her. Do not under any circumstances spend any time with her alone, even if there are people nearby. Do not include her in any chol hamoed activities, and do not allow your girlfriend to include her. Just say that you want to spend time with your girlfriend.

Utilize yom tov to determine if you actually and sincerely want to have a future with your girlfriend. You will be spending a full week with her, and both families. This should hopefully give you more clarity. If it doesn’t, then after Pesach, you need to come clean and tell your girlfriend that you are not ready to get married and allow her to determine the next step. If it turns out that your relationship does end with your girlfriend, then I advise you to give it a long period of time before you pursue that friend. 

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis and shidduch consultant. She can be reached at Baila also hosts The Definitive Rap podcast for, Israel News Talk Radio, WVIP 93.5 FM HD2, and Questions and comments for the Dating Forum can be submitted to Read more of Baila Sebrow’s articles at


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