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Gruber: My kippah conundrum keeps kicking questions at me

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Kippot have been very much in the news lately, what with Germany suggesting that its Jews not wear them due to a rise in hate crimes, and a knife-wielding terrorist in Australia targeting students “wearing the Jewish headgear.” It certainly puts my personal head-covering decisions into perspective.

As one of a very small number of modern Orthodox Jews (a term that had not yet been invented) growing up in Rochester, N.Y., I was constantly struggling with when to wear a kippah. Putting it on my head when I attended the city’s only Jewish day school was a no-brainer. As was taking it off when I went into a non-kosher restaurant for a “vegetarian” meal, as was the norm at the time.

But the remainder of the day was not so black and white. As an awkward adolescent trying to fit in, how much did I want to brand myself as a Jew when I went about my daily activities? Should I wear it on the tennis court? To the supermarket? At the movies?

My conundrum became even harder to manage as I entered public high school, then university. My sense of Jewish identity remained strong, as did my observance level – keeping kosher(ish), being shomer Shabbat, even putting on tefillin every day. But I was also as modern as a modern Orthodox Jew could be – going out on dates, to clubs and concerts. Did I really want to be “that guy with the beanie”?

The pockets of my jeans were well-worn from the constant in-and-out of my kippah. And yes, I had a collection of every type of hat imaginable, one to suit every occasion: baseball caps when I wanted to look like a regular Joe; cowboy hats and fedoras when I wanted to play dress up; even an authentic French beret when I was feeling hip and intellectual. Thirty years later, my hat collection has only grown.

You’d think that as a fully functioning adult I would have moved past this grey area by now. But these kinds of decisions continue to haunt me on a daily basis. I put my kippah on when I visit friends in my old Bathurst Street neighbourhood, then take it off again when I come home to my apartment in the Beaches. I wear it when I go to a kosher restaurant, but not when I go to a bar for a drink. It sits on its familiar perch when I go to my Jewish dentist’s office, but not when I visit my Catholic family doctor. I keep a kippah handy the way a diabetic keeps insulin: in my pocket or the glove compartment of my car, ready for an emergency at any time.

And the decisions only seem to get more complex as I get older. Do I wear a kippah as I attend the mixed marriage ceremony of good friends? (Answer: no, unless they invoke the name of ha-Shem under the huppah – then I quickly whip it on and off). Do I wear a kippah as I attend a bar mitzvah party at a non-kosher venue? (Answer: yes, but sneak off in a corner if I’m going to eat any “vegetarian” nibblies). Do I wear a kippah to the screening of a documentary about the Holocaust? (Answer: probably, but depends on the exact nature of the movie and/or film festival it is being shown at.)

This brings me to the two most recent dilemmas I was grappling with. The first involved a fundraising event I attended for a grassroots organization dedicated to building traditional and Jewish life in Toronto. Normally, this would be a definite “yes, kippah,” but the event was being held in a very hip venue in Kensington Market, an area that I visit frequently, uncovered. I was somewhat reluctant to be “outed” if I bumped into one of my musician friends. But after much agonizing, I decided to wear it proudly, and was glad I did.

The second decision was a little more difficult. Relatively new to the dating scene post-divorce, I was going on a blind date with a woman who friends had fixed me up with. I knew she went to an Orthodox shul, but had no idea of her level of observance. We were meeting at a coffee shop. What did I want to impart as a first impression? In this instance, I decided to go kippah-less. I felt more comfortable that way, and figured if she didn’t accept me for who/what I am, it wasn’t going to work anyway. No great surprise, I spent the better part of the date trying to explain who/what I am! (Needless to say, it didn’t work out.)

My internal struggle about when – and when not – to wear a kippah involves thousands of years of history, persecution, guilt, family, therapy sessions (and of course, more often than not, food). At its core are issues of identity: Where did I come from? What exactly am I now? Who is the man I wish to become?

The dilemma continues, likely never to end. There’s so much to wrap my head around – adorned with a kippah or not.

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