By Baila Sebrow


After much aggravation with dating, I have a problem that most girls my age wish they had. This is my shidduch story. I didn’t go to seminary in Israel after high school. Instead, I went straight to college, and graduate school, and I finished, got an amazing job, and was quickly promoted in my company before other people got started!

It all began for me with finding a shidduch by going to shadchanim, but they made my life miserable. I never understood why it was their business of why I didn’t go to Israel, or why they decided on the type of guys I should date. They are not Hashem! One popular shadchan put me through the wringer with her warped questions when she interviewed me. For example, she asked, if there is one thing that I could change about myself, what would it be. I told her that it’s a hard question, and she said, “It’s not supposed to be easy.” Really? Anyway, I didn’t answer her, because I wasn’t sure what to say, and she told me that she can’t help me! That was a long time ago, but I just want you to understand where I’m coming from, so you could help me with my problem.

Since things were going so badly for me going the shadchan route, I decided to use a dating app. Suddenly, a new world opened for me. The same guys I was interested in whom the shadchanim refused to set me up with, on the app they wanted to go out with me!

Now, there are two guys on the app who I really liked, and I couldn’t choose which one to go out with. My parents told me that there is nothing wrong with going out with more than one guy until I have a ring on my finger. So, I listened to them, and now I like both guys I’m dating! The difference between the two is really money. One guy has more than the other. They are both great guys, and they treat me so well, and I have to choose between the two. I know this is not your typical letter, but my parents tell me to take the guy who has more money! What are your thoughts about this?


Your problem is not as uncommon as you might think, specifically where it relates to the prejudices, preferences, and judgmental attitudes towards anyone who appears to be distinct in any area. Whenever I hear of a story where a shadchan decided who one is compatible with and who is not, it makes my blood boil. If a shadchan chooses to engage in the profession/chesed of shadchanus, her or his job is to introduce people to one another. They have no business judging anyone. Nor do they have the right or qualification to play mind games and psychoanalyze a single man or woman. Your story about the shadchan who insisted that you tell her the one thing that you could change about yourself, really takes the cake. For, starters, that is a very personal question, and I am happy to hear that you didn’t respond to her. Shame on her for refusing to help you find your bashert.

It is no wonder that you now find yourself in this dilemma. Your experience with shadchanim has been bad, so you did the right thing by being proactive in finding dates for yourself. How interesting that the guys whom you wanted shadchanim to set you up with ended up going out with you! However, you were likely still so traumatized from your negative experiences that when it turned out that two guys liked you at the same time, you were afraid to say no to either one of them. I will say that the viewpoint of your parents regarding a young lady dating as many men as she wants up until there is a ring on her finger was very common in their day. Nowadays, the mehalech is that women date one person at a time. Some people might even consider it cheating if she dates more than one man. In my opinion, I believe that until a woman has a verbal commitment from a man made in front of family members, (even though not yet officially engaged) pledging his sincerity of the relationship, she is very much still single.

You are now in distress about your predicament. As the saying goes, “when it rains it pours.” It would have been great to have met just one of them during those times when you had no guy available for you to date. But not everything in life has perfect timing. Who do you choose now?

Do any of these guys know about the other? The frum world is even smaller than you think. You don’t say how long this has been going on with these guys, but I can’t imagine that if you go to public places like restaurants that people you know haven’t seen you with at least one of the guys. I would not be surprised if one of them may know about the other.

The fact that it has come down to your need to choose tells me you are feeling the seriousness of the relationships. You have two options. You can continue as you are doing, but, I don’t think that could end well. You will be getting more and more confused. Your other choice is to tell both guys about the other and explain that you dated both under the advice of your parents. A confident well-adjusted man will understand where you are coming from. At that point, he will feel obligated to express his true intentions, and it will also give him the opportunity to discover if he cares. If he is not serious about you, he may not care. You are also taking the chance that one of them will get so mad that he will drop you.

I am also wondering, is it possible that it is not so much about having to choose one over the other, as it is for you to know that here is a man in your life, considering what you had been through? It would not be unusual for you to feel as though you are now being vindicated for past hurts. Dating these days has become so difficult that oftentimes women just jump into relationships with anyone who wants them. In your case, it is two men at the same time.

I can understand why your parents feel you should choose the guy that has stronger financial footing. They are looking out for your future from a different angle, as that of parents to a child. No disrespect to them, but I don’t agree with their recommendation. Unless that guy has other impressive qualities, having a few dollars more does not automatically make him a better contestant as a future husband.

I believe that each of these guys brings something different to a relationship that the other does not fulfill. That’s normal. No one person fits the entire bill. I am sure that you are attracted to whatever unique quality one has that the other lacks. No doubt, the same for any negative traits which the other guy somehow makes up for. And so together as one package these two relationships worked for you in the beginning. Ask yourself if you would have even considered any of them for marriage had they both not been in your life at the same time and had past shidduch experiences been different.

My concern is that whatever happens, you will have no regrets and be at peace with yourself. That is why I am going back to my original advice of telling each guy what has been going on. It is possible to avoid that sort of uncomfortable conversation by first taking some time for yourself away from dating to reflect on the occurrences of recent. Use that period to also find out more about each of them.

As much as I encourage singles to meet and find dates on their own, the downside is that you do not always get the same opportunity to investigate the individual who may become your future spouse and parent of your children, iy’H. You or your parents should be calling the rabbi of their shuls, and also speaking to people in their respective communities to find out as much as they can. How did they live their lives in earlier years, and what are they doing now? What is the general objective opinion about them? It could be that after all that, your problem of having to choose between the two guys will no longer be the case.

The blessing of having time is that not only does it give one the opportunity to heal, but when you are not in the presence of whatever you are dealing with it offers the chance to reveal aspects that you may have overlooked. Taking that time and space away to think and finding out more about each guy should help give you more clarity. The upcoming chagim is now the best excuse for requesting that time.

If it turns out that both guys are great, and they each have no problem that you are dating the other, you will be forced to choose by dating one guy at a time, or perhaps none of the two. This situation will have hopefully allowed you to recognize that there are men who want to date you and be in a relationship with you. You are not in the same place as before when shadchanim refused to introduce you to a plausible shidduch. What is it that you are looking for in a husband? That is where your focus really needs to be. n

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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