Dating

Question

I went to a Chassidishe school, but never really fit in. Even though I dressed like the other girls and had friends, I still felt like an outsider. After high school, I stopped wearing Palm stockings and started wearing thin ones with open toe shoes and colorful dresses. My parents were okay with it, and they told the shadchanim that I’m looking for a Litvish boy. I got redt all kinds of ex-Chassidishe boys who were interested in me, but not Litvish. The Litvish shadchanim were not sending them my way. Those boys didn’t want me. I figured that maybe I should start looking and dressing more modern and find a shidduch myself.

I started going to modern places and wearing pants there. The boys there were interested in me, but they were not for me, and between you and me, I don’t want to even wear pants. I just don’t know what to do or where to look for a shidduch. I want to cover my hair when I get married and look like a regular Bais Yaakov girl, but those types of boys don’t want me. How does a girl like me find a shidduch? Where do I belong? Is it too late for me to do anything about it?

Response

It makes a lot of sense that you’re confused and stuck. You tried to find your place between worlds and each world reads you based on what it sees, not on who you are. That’s exhausting and isolating. But the good news is that the type of guy you’re describing does exist. And you don’t have to reinvent yourself or compromise to find him. You just need to adjust how you’re presenting your story and where you’re looking.

Your letter carries a quiet ache that many people recognize, but few articulate so honestly. Feeling like an outsider while technically “belonging” is one of the most painful forms of loneliness there is and it often follows a person far longer than they expect. The fact that you were able to name it, and you kept searching rather than giving up, speaks volumes about your strength.

What stands out most about your story is not confusion about values, but confusion about categories. You were raised in one world, but never quite fit in, so you experimented with another world that didn’t speak to your soul either, and now you’re being told (not in so many words) that there’s no place left for you. That message is not only untrue; it’s downright unfair.

You’re not asking for something contradictory.

Wanting a Torah-centered life and a home grounded in Bais Yaakov values does not require following a perfectly straight line to get there. Life is not a résumé and people are not disqualified because they need time to understand themselves. It’s important for you to clearly accept that the problem is not who you are—it’s how the shidduch system interprets stories that don’t neatly fit all the boxes. Systems prefer simplicity; people are more complex.

When shadchanim hear that someone grew up Chassidish but no longer dresses that way, they often jump to conclusions that don’t reflect reality. They may assume instability, rejecting tradition, or a lack of clarity about the future, even when none of that is true. Meanwhile, when you present yourself in more modern settings, the men who approach you are responding to the signals you’re giving, not the values you hold inside. Clothing, environments, and social circles communicate intentions whether that is our intention or not.

None of this means you made mistakes. It means you were searching, and searching is not the same as rebelling. The question now is not “Where do I belong?” but rather “How do I communicate where I’m headed?”

You already know what you want: a committed Jewish life, tzniyus, covering your hair after marriage, and a normal, warm Bais Yaakov-style home. That is not an unreasonable dream, and there are men who want exactly the same thing, including men who are open-minded enough to understand that not everyone’s path looks identical.

What may help is to align your presentation with your destination. That doesn’t mean erasing your past or pretending to be someone you’re not. It means allowing the outside to reflect the future you’re building rather than the phase you’ve outgrown. When people see clarity, they respond to it. It may also mean being selective about who represents you. Not every shadchan is equipped to advocate for someone with a nuanced background. Some rely on shortcuts and stereotypes. Others understand that sincerity, direction, and character matter far more than labels. Finding the latter can make all the difference.

It comes across that you might be a bit hard on yourself. Please be gentle with yourself. You are not broken, late, or “too much” of anything. You are a thoughtful person who took the time to understand herself—and that is precisely the kind of person who builds a meaningful marriage.

The right man will not be looking for a perfect backstory; he will be looking for a real person with clarity of heart and intention. And when the message you send to the world matches the life you want to live, the right people will be far more likely to hear it.

So, let’s get to the bread and butter of how you can attain your goal. It’s not that the Litvish guys don’t want you. It’s that the shidduch system doesn’t know how to categorize you. When shadchanim see a Chassidishe background, shifted style, a period of trying out modern places, wearing pants in some environments, they don’t hear your destination. They only hear your journey. Litvish boys (and their parents) usually want a clear-cut Bais Yaakov girl with stable hashkafos and a predictable future home. You actually want that too, but your story confuses the system because it might seem (though inaccurately) that you are off the derech, which is why you were being suggested to ex-Chassidishe guys. The thing is that you’re a young lady who never fit the Chassidishe culture and you’re trying to find the place where you belong. But unless you explain that clearly, shadchanim will fill in the blanks with the wrong assumptions.

You need a new, clear, strong profile narrative in your bio that sounds something like: “I grew up in a Chassidishe environment but never really fit the style or culture. I’ve always had a more Bais Yaakov or Litvish hashkafa, and that’s where I see my future. I want a warm, normal, growth-minded Litvishe home, tzniyus, covering my hair after marriage, and a Torah-centered lifestyle. I’m looking for a guy who appreciates sincerity over labels.” When shadchanim hear that, everything shifts.

Present yourself the way you want your future to look. You don’t need to pretend because the style you’re presenting signals where you’re heading. If you want a Litvish type of guy, dress like the type of wife you plan to be later, not Chassidishe, not modern with pants, just a regular Litvish or Yeshivish tzniyus young lady with knee-length skirts, normal tops, and a polished and poised look. It’s not selling out—it’s telling the world clearly who you are and who you want to be.

You’re not the only one with this story. Many girls from Chassidishe schools and Chassidishe families end up marrying wonderful Litvish boys—once they are matched with shadchanim who understand them. I will leave you with a story that happened in my shadchanus. The mother of a young lady called me in distress saying that her beautiful daughter cannot find a shidduch because she comes from a Chassidishe home, but she’s not looking to marry a Chassidishe bachur. The mother also explained that her daughter dresses in skirts that do not cover her knees nor does she completely cover her elbows. Thereafter, I had an idea about a guy who I felt might be a good match for her. He immediately declined the résumé after reading about her background. A few weeks later, I organized a singles event and the young lady immediately registered to attend. I did everything in my power to see to it that this particular young man attended as well. I was certain that when they met in person, there would be an instant mutual attraction. Furthermore, I was confident that when they spoke, he would understand who she was and where she was going in life. With Hashem’s help, the story had a happy ending, just as I predicted. Today, Baruch Hashem, they are happily married with a beautiful family. Your background is not a problem. What matters is your direction, and for the person who represents you to “get you.”

Your journey, with all its twists, growth, and inner strength, will not be a barrier, but part of your story that makes you “you.” The right match will see your heart first and your story second. Keep holding on to your values, speak your truth with clarity, and trust that the right match will be drawn to you. Keep believing that there is someone who appreciates your sincerity, direction, and commitment to the type of home you envision. Your path may have had unexpected turns, but it has led you exactly where you need to be. Stay true to your values and don’t lose hope, because the guy you’re looking for is looking for you too. 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. Baila also produces and hosts The Definitive Rap podcast for 5townscentral.com, vinnews.com, Israel News Talk Radio, and WNEW FM 102.7 FM HD3, listenline & talklinenetwork.com. She can be reached at [email protected].