And on it.
“Sometimes I wish I could just do this normally.” There are times when I’m out – at the mall, on the streets of the East Village, at a pub… wherever… that I catch myself thinking this. Ordering a beer has become an entirely new enterprise.
“Will she be more attracted to me if she only looks at the front of my head?” There are times when I wonder if girls think different of me because they have to make assumptions as to who and/or what I’m interested in.
I’m no stranger to second-guessing things a little too much, but a month and a half into the great kippah experiment, I notice that in my mind, I’ve started to equate not wearing a kippah with “what was normal” and wearing a kippah with “abnormality” (no pejorative intended). Maybe it’s supposed to be that way. Maybe that’s what this experiment is all about. On that note is it even legitimate to experiment using ritual garb? Is it taking advantage of a holy object? Is it being a little too egocentric and selfish?
There are times when I imagine it would be easier to just not wear it. But I think it’s partly all about the struggle. In fact, I’m GLAD I’m struggling with it. If at some point wearing a kippah became a mindless act, akin to wearing jewelry… wouldn’t that defeat the point?
Case in point: I wear an earring. When I got my ear pierced in grade ten, it was partly an act of defiance, partly an act of shedding my perceived earlier dorky appearance, and partly an act of impressing the girl who sat next to me in math. It was her idea. At the time, I thought about it everyday, and I knew that people looked at me differently. And that was the point! Now… it’s just a part of who I am. I play with it occasionally when I’m bored, and I suppose that it’s become a little bit of my persona. But it’s no longer an item which I consciously use to project a part of my identity.
At this point, the kippah is like the earring was in Grade 10. It’s a direct external signifier of an internal message. A flag. A billboard. After six weeks, this is where I am. Struggling, but thinking that the struggle is part of it all. Yisrael and all that.
I’d be curious to hear if those who wear kippot on a daily basis think about it each day. I hope they do. I hope I will a year from now.
Rabbi Jesse Paikin 
I hate to suggest this, but maybe you’re thinking about it a little too much? I understand the struggle, I went through it myself years ago. But, at the end of the day, it’s just a piece of cloth head covering. Not holy, and only as much of a statement as you want it to be. Don’t let the kippah define you, let it express your relation with God and other Jews. Roll with the punches, and revel in the great comments. And, always, try to think about it a little less.
Yasher koach bro!
The whole point of this project is to actually think about it. REALLY think about it.
The kippah doesn’t define me wholly, but it is representative of some beliefs that I hold. And, as I noted above, I think people need to think about it a little more.
If, as you suggest, “at the end of the day, it’s just a piece of cloth head covering,” then why do we bother to wear it at all? I think at the end of the day, it’s a flag and a billboard and I think that people don’t think of that enough. They don’t think about what they’re representing.
Not holy, David? What on earth does holy mean then?
Jesse, I’ve had a similar experience with a different article of clothing. You’re no stranger to tzitzit because you were them on Shabbat (or did at one point, I can’t remember now if you still do).
The first couple of months, it was struggle even to remember to put tzitzit on. Now, if I don’t, I feel naked. On Saturday night, Halloween, I was all bent out of shape over whether to include tzitzit in my Super Waldo costume. The problem was resolved when a friend was being chasidic Waldo and needed to borrow the only pair available at the time.
In any case, I think it’s not working if I don’t think about is regularly.