I've struggled with the question of when to where a kippah for quite some time. It all started when I went to Kutz for a summer. In an enviroment that encouraged ritual experimentation, I embraced the opportunity to try out everything. During the Amidah, I actually took the time to read through all of the blessings that were often skipped over in my synagogue growing up. I began to ask questions about prayer choreography, making sure that everything I did was intential, and something that I found to be meaningful. There was a small minority of female campers/staff who chose to wore a kippah. The times they wore it varied. I started some conversations with them to find out why they do what they do. My first summer on staff I decided to wear a kippah every day. In an environment like Kutz, it is common to see outward displays of Jewish pride. Whether it was a NFTY t-shirt, Jewish star or a Hamsa necklace, symbols of Judaism could be seen everywhere. In the Kutz bubble, I felt free to be who I was. No one (outwardly) judged me, and I felt comfortable expressing myself in that way.
On a day off from camp, my friends and I drove to my house to hang out. I had my kippah on when we left camp, and by that point it was just something else I put on in the morning when I started my day. I walked into my house and realized that I had made a mistake. I watched in horror as my mom insisted that I take my kippah off, embarrassing me in front of my friends, and reminding me that not everyone feels the same way I do about Judaism. I don't know why my parents disliked the kippah. Maybe they thought it was weird? Maybe they had their own negative experiences with more observant Jews who chose to wear kippot? Whatever the reason was, it frustrated me to know that I could not practice Judaism the way I wanted to at home.
I decided to conduct a very short-lived experiment. I wore my kippah to school (I went to a public high school.) I'm not sure if my parents even know about this because I put it on after I left the house. I think it lasted for two days. I got one uncomfortable comment from a teacher, and that was the end of it.
I eventually settled upon just wearing a Kippah on Shabbat and Chagim. For much of a high school when the only thing I "did" to celebrate was go to Temple, I used my Kippah as a physical reminder that today was different.
In an environment like AHA, I've started to reconsider my position on kippah wearing. Some Jewish professionals I know never wear a kippah. Others only wear one when they are "working." Others only wear one when praying. Wearing a kippah definitely sends a message. I'm just not so sure what message I want to be sending right now...
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