In recent weeks my Facebook page has been dominated by my friends joining a group called “Support Jonathan”. The Jonathan in question is Jonathan Escobar, a teenager who was recently expelled from school because of the way that he dressed. Jonathan dresses in feminine clothes and the school said that he should “dress more manly or consider home-schooling”, citing their dress code prohibition on wearing clothing that "contributes to a disruption of school functions." Jonathan recently moved to the school in Georgia from Miami and said that he had talked to the school about the way he dresses before he began classes and they said it was OK.

What is interesting to me is that the demand by the school was not just that he change a certain thing about his clothes—no brightly colored wigs, no stilettos— but instead that he dress more “manly.” I wonder if they would make a similar demand of a girl who came to school in short hair wearing “boy’s” clothes? Is the prohibition against cross-dressing? Against certain items of clothing that aren’t appropriate for school? Or against being gender non-conforming?

As a Jewish educator this question has particular resonance. Not just because of the possibility of this happening in my classroom, workshop, camp bunk, or program (truthfully, I wouldn’t flinch if it did), but because of the apparent prohibition to “cross-dress” in Judaism stemming from this verse from Deuteronomy 22:5: “A man’s clothes should not be on a woman, and a man should not wear the apparel of a woman; for anyone who does those things, it is an abomination before God”.

In Judaism in recent years this debate has not been around transgender or gender non-conforming Jews (though it does come up when, for example, a bat mitzvah girl wants to wear a pant suit instead of a dress), but with Jewish woman who have begun to wear “kli gever” – “men’s things” such as tefillin, talleisim, and kippot which are the focus of the prohibition in rabbinic literature because they are items only required by halakha for men. The liberal/progressive Jews don’t hold a different halakhic obligation based on gender, so this prohibition becomes irrelevant in that case.

But I don’t want to stop there, because if we do we’ll miss something beautiful found in the Babylonian Talmud.  The rabbis of the Babylonian Talmud didn’t read the verse from Deuteronomy as a ban on cross-dressing, “but  a ban on wearing clothes of another gender in order to falsify your identity, infiltrate spaces  reserved for the opposite sex, is what is forbidden.”  (Rabbi Elliot Kukla and Reuben Zalman, Torah Queeries, pg. 255) So we learn that according to the Talmudic rabbis this verse comes to urge us to be our most true selves and make sure we are in spaces that are safe, appropriate and consensual for everyone. This is exactly what I hope for any educational environment I am a part of.

So, this brings me back to “Support Jonathan”. Yes, I do. I support him being able to be who he is, express himself, and safely attend school. On a few news websites I visited about the story they are conducting a poll of the viewers asking as to whether you agree with the school or with Jonathan. Devastatingly, nearly every site’s results side with the school and assert that Jonathan should not be allowed to dress “like a girl”, 80 to 20.  Though this is unfortunate, it is not surprising. Gender non-conformity, as we know even from within the Jewish world, is consistently met with hostility, resistance, and even violence.

Our work here at Ma’yan is to pay attention to these trends in the context of teens’ experiences, needs, and desires and then to match the ways we teach or parent to be accountable to the youth we have in our care. This story, which I suspect many of the teens we know are also talking about, provides just that kind of opportunity. Raising this story in a Jewish framework provides us with the chance to revisit the commitments of our institutions to being inclusive of all genders and of Judaism to encourage all of us to be our most true selves.