By Baila Sebrow


I recently read an advice column featuring a letter-writer who called himself the “black sheep of his family.” My wife and I discussed this, and we are concerned about the frum Jews who grew up in yeshivish or chassidishe families but chose to be frum Modern Orthodox instead. We know many people who are in this category, and, baruch Hashem, most of them are married.

Unfortunately, we know others who are in this situation but remain single. It is very difficult for these single men and women because they have “fallen through the cracks,” as they do not fit the mold of yeshivish or chassidishe or Modern Orthodox and they are not “off the derech.” My experience with frum singles is that they unfortunately tend to become less frum the longer they remain single. In addition, many of their parents shudder at the thought that their children feel more comfortable in a YU/Stern environment than in a yeshivish or chassidishe environment.

My wife and I thought of a way that could help those who grew up in these “to-the-right” households but want to be frum Modern Orthodox. A group could be created that caters to people in this situation. Based on interest level, appropriate and enjoyable social activities for this group could take place in the Brooklyn/Queens/Long Island area for these individuals. If the need arises, discreet referrals to mental-health professionals could also be made. These individuals should know that the frum Jewish community cares about them and do not want to “write them off.” This group will enable those from similar backgrounds to realize that their situation is not unique. Another positive offshoot could be that shidduchim could result from this endeavor.

Due to time constraints and lack of experience in these areas, I am unable to initiate this group. Perhaps you or others could influence others to start this group. Thank you for having a forum for singles to be able to express their dating and relationship concerns.


There is a very big difference in the upbringing of one who was raised chassidish and somebody who was raised yeshivish. And there is still more disparity in the educational level between the genders, too. Girls who are educated in chassidish schools, for the most part, have greater secular academic opportunities than boys. In yeshivish schools there is less inequality within the curriculum. When yeshivish young people graduate from high school, both the men and women are usually scholastically on par, and many are therefore able to attend college and oftentimes seem no different than those who were raised modern.

When it happens that a yeshivish type of child decides to become more modern and steers towards a YU type of hashkafah, it is not so big a culture shock for their parents. They may not like it, but there is less of an antagonistic reaction than when it happens in chassidish households.

The problem is not so much that these single men and women decide to become more modern. It is quite common in all hashkafic circles that as children grow into young adults, they may choose a slightly different mehalech than the one in which they were raised. If it’s a little more to the right or left, that is in most cases acceptable to their family and community. However, when the shift is many degrees to the left, it is not a mere adjustment of the shape of the hat, style of yarmulke, or color of the shirt. There is much more going on, and that is one of the concerning aspects and the reason these young people experience so much rejection. If you have ever had the opportunity to speak to them about why they decided to alter their hashkafah, they will oftentimes disclose that it stems from a feeling of hypocrisy they experienced either in school or at home. It can also be an act of rebellion as a result of past hurts that they may have been subjected to as youngsters.

The reason these young men and women remain single and fall through the cracks is sometimes a result of their own doing, because they have not made peace with their inner demons and, more importantly, they are still struggling with their religious identity. I have met many such singles and they are not able to feel completely at ease in any hashkafic group. Chassidish men (and also women) struggle with accents and also American-style lingo. Even when they are accepted in various social circles, they rarely feel a sense of belonging, and they openly express that notion.

Yeshivish men and women, on the other hand, have it a bit easier in adjusting to Modern Orthodox circles. It is not uncommon for a great percentage of shidduchim to occur between Modern Orthodox and formerly yeshivish people.

The biggest issue is reaching out to former chassidish men and women with shidduchim. Helping them find a shidduch can be quite the challenge because they sometimes cannot find their niche. You and your wife feel that if communities can somehow figure out a way to gather them all together then we could help them. But it is not so simple. In most cases, they don’t want to marry somebody who comes from a similar background because it is too close for comfort. Remember, they left because they were not happy, and even though it makes sense that they should gravitate towards one another, they typically reject someone who is very much like them. In nearly all situations when they do marry successfully, the spouse is very sensitive, patient, and understanding, yet from a modern background.

Although this also includes women, I will say that a majority of challenging shidduch cases that I get are from the male singles who come from chassidish homes and have turned more modern. My heart breaks for these beautiful souls because they have so much to offer, yet they experience the most rejection in the non-chassidish circles. They are not even given the chance to meet someone compatible with them. If they find a shadchan who wants to deal with them, as soon as the shadchan tries to suggest them to somebody, the idea is shot down, without meeting first. Those who decline them do not realize that those who were raised chassidish have so much value to contribute as spouses and parents in terms of the manner of conduct in the home. They typically have very warm and approachable personalities, which is a product of their upbringing. Additionally, chassidim also possess a wonderful sense of humor that is reminiscent of the European shtetl days, where a sense of humor was necessary for survival, and it is therefore passed down from generation to generation. Life can bring much travail, and those who can find ways to laugh are the one who endure best. Moreover, most chassidish young people are coming from homes where there were many children raised under the same roof, and where the older children took care of their younger siblings. That oftentimes implies that they have a built-in sense of responsibility where it relates to childcare.

There are people who have married an ex-chassid or those who have just gone a bit more to the modern side, and they will confirm that everything I am saying about them is accurate. However, for someone to agree to date a person who comes from a different type of upbringing would mean that they have to first go through their own challenges and journeys to reach that point of understanding and acceptance.

What you and your wife are attempting to accomplish is wonderful. You both have your hearts in the right place, and it is important for every Jewish community to make sure that those who are “out-of-the-box frum” never fall through the cracks. But rather than have specific groups for them, why not provide avenues to integrate them within the hashkafic circles that represent who they are now? The world of dating has enough labeled groups and subgroups, and new ones are being created each day. All that has ever accomplished is less acceptance from society and more personal feelings of not fitting in. And besides, frum people have enough history to show that selection of any kind proves harmful.

So, realistically, how can one be most helpful to those who veered to a modern way of life? Discretion is the key word. It sounds like you and your wife have an open home or open line of communication where singles of various backgrounds feel comfortable with both of you. You likely become close enough with them that if you feel somebody can benefit from mental-health counseling you can refer them to a professional. But here is the issue. They should not be made to feel that they are part of a group of people who need counseling or a club in Brooklyn, Queens, Long Island, etc. Giving them such an impression will turn them off altogether, and it can steer them towards becoming less frum.

That brings me to your comment that the longer they stay single, the greater the likelihood of becoming less frum. Just so you know, that is a common phenomenon that can happen to anyone, regardless of the way they were raised. There are many reasons why that could come about. The major factor is “the grass is greener on the other side.” When people feel unsuccessful in their endeavors, they begin to look elsewhere, especially in what feels like less religiously restrictive circles. And from the outside, most things appear more appealing.

Those who “fall through the cracks” can also be people who feel ignored by the system. Falling through the cracks is seen in educational institutions that ignore students who are not academically on par with the rest of the class. The same thing happens in shidduchim. Those who are dissimilar are immediately dismissed, whether it is in areas of hashkafah, physical appearance, or even financial circumstances, etc. There are shadchanim and people who will only help those they deem perfect. It is those people who are creating a “fall through the cracks” situation. And sadly, while these people are sitting comfortably, they have no clue how serious a matter we have, where singles are assimilating and even intermarrying, R’l. It behooves every person to reach out to singles in their community or those they encounter to introduce them to someone. Everyone knows somebody. And it’s about time that people learn from the bad and reconstruct it into something good.

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 Questions and comments for the Dating Forum can be submitted to Read more of Baila Sebrow’s articles here.


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