By Baila Sebrow

By Baila Sebrow 

I really enjoy reading your column with my friends every Shabbos. It’s enlightening, informative, and entertaining, and leads to lots of meaningful discussions around the topic of shidduchim. I’m reaching out to get your advice about my friend.

I hate putting people in a box, but I would describe her as very frum in the sense that she’s very spiritual. She davens every day, learns Torah when she can, and has a real connection to Hashem. She even goes out of her way to make sure to daven with a minyan on Friday night. She’s strictly shomer kashrus and shomer Shabbos, has impeccable middos, and values a Torah lifestyle in the home.

The problem is that in her dating life she hasn’t been so successful. One of the reasons that guys break up with her is because they find out she wears pants in public. In other words, she’s extremely frum, but she happens to wear pants. She wears skirts on Shabbos, but she wears pants for the most part.

There are, of course, guys out there who don’t care if their wife wears pants in public, but, generally speaking, they may be lax in other areas that she cares about. The predominant view of a guy who values learning, keeping halachah, and davening three times a day is that he won’t go out with a girl who wears pants in public. And that seems to be her Achilles’ heel.

She typically wears skirts on the first few dates to build a connection and so that the guy will hopefully see her for who she is. Then on the third date she wears pants to see how the guy reacts. Unfortunately, ten times out of ten the guy breaks it off because of that reason.

I’m a big proponent of just being yourself on a date, but if she insists on going out with frummer guys, she’ll have a very difficult time attracting the type of guy she wants because I don’t believe this guy exists (or at the very least is very difficult to find).

How would you advise my friend? Should she continue being herself and wear pants after the first or second date, or should she hide that fact until much deeper in the relationship? I’ve heard lots of cases where the girl wore skirts until she got married and then decided to go out in pants occasionally, and the husband doesn’t seem to care at all. Of course, he would rather that she wear only skirts in public but by that point he loves his wife for who she is, and it doesn’t really affect him as much or at least it’s something he tolerates. 

Please shed some light on this issue.


Your kind words and readership are very much appreciated. Moreover, your question is welcome, as there are many singles who carry the burden of this dilemma but are ashamed to bring it to the forefront. Instead, they complain to their friends who are experiencing the same frustrations, with no apparent solution in sight for them.

I have been a shadchan and dating coach for 40 years. Granted, I was very young when I first became active in this field of chesed, but the question that your friend is grappling with would not have been an issue in the minds of most people in those earlier days. Back then, young ladies such as your friend were very common. I witnessed young ladies in pants who davened three times a day with more kavanah than some young ladies who wore skirts. So I get where your friend is coming from. But before I comment further and offer advice, I must make the following disclaimer: I am not a posek, nor am I responding from a halachic perspective. For that I urge you to contact your local Orthodox rabbi.

The world of shidduchim is one of frustration. Years ago, when singles actually got married at greater frequency than today, the term “hashkafah” was never uttered in relation to shidduchim. And even in the years before my time, Orthodox shuls with esteemed rabbanim at their pulpits hosted dances in their ballrooms where their congregants and other frum young men and women came to dance together, and many eventually married each other.

Interestingly, the issues of assault and “ghosting” in dating relationships, and other dysfunctional behavior, did not happen at the same rate of occurrence as today. Not only that, but the horror stories that come my way via phone, e-mail, and text are mainly from what one would consider the more right-wing daters. Let’s also understand that these are not real frum people, though they consider themselves to be “to the right” and dress the part. Anyone can play dress-up and pretend to be whoever they want to portray. The bottom line is that it has been ingrained, especially in the minds of young ladies, that if they want to have a good life and build a bayis ne’eman b’Yisrael, they need to marry a guy who is known to be “machmir.” There are countless young ladies who were raised in Modern Orthodox homes, went to Modern Orthodox schools and camps, and after returning from their year in seminary, they changed their dress style and entered the shidduch scene looking for a guy who is to the right in hashkafah. At times those relationships worked out, and other times it did not. After the dust settled and they were married, there were those who found themselves questioning their hashkafic identity.

I don’t know much about your friend, other than that she wears pants and is honest about it, but I admire her honesty and sincerity. She is not just honest to others; the hardest thing for most people is to be true to themselves. However, doing the right thing in life does not always guarantee an immediate positive outcome. That said, it appears as though she is stuck between a rock and a hard place, but she is really not!

Your friend wears pants but wants a guy who davens three times a day, values learning, and keeps halachah, because that is with whom she feels compatible. This young lady is being described as “very frum, spiritual, davens every day, learns Torah, and has a connection to Hashem. There is no way that she can date and marry a man lacking in any of those areas, because, as you say, he will be lax in other areas, contrary to how your friend wants to live life as a bas Yisrael and eim b’Yisrael.

You mentioned that there are cases where the young lady misrepresents herself and wears only skirts until she gets married and then reveals her true self after marriage, and the husband goes along with it. You might think that the husband doesn’t care. But there is no doubt in my mind that he feels betrayed by the deception. He might tolerate it externally, but it is the start to the fraying of the relationship. People get married with the expectation that their spouse was open and honest about who they are and their goals and aspirations for the future. If some time into the marriage it comes to light that it was all a façade, no one ends up happy.

Your friend needs to continue being true to herself and what she believes in with regard to hashkafah. Thus far, she has not found the type of guy she is looking for. But that could be said about young ladies with other types of hashkafos, for whom it might be assumed that things are easier for them. It is not. I am of the opinion that your friend is not likely to find her spouse through a shadchan, because people are not always completely honest with the shadchan when describing their own values. Also, there are shadchanim who might think it is OK to introduce people who do not seem compatible at the outset, but they manage to make it work. I am not criticizing their methods, because they are focused on making shidduchim. Such maneuvers will not work in your friend’s favor.

Rather, she might benefit from singles events where she can dress as she is, and any man interested in her will have the opportunity to talk to her and find out about her true moral essence. That will either eliminate the wrong types of men or draw the right one to her. Dating apps, where she can describe herself, is another way to go in her case. Other options are visiting communities that are Modern Orthodox so she can network and get to know the people who live there. There are young men who are shomrei Torah u’mitzvos, yet are modern in dress, and are accepting of a young lady who wears pants outside the home.


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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