It’s well over 15 years later, yet I vividly remember laying out my clothing the night before the “Big Event,” the first day meeting the JEP kids: a button-down shirt with a light green sweater complete with a pleated skirt. (Which may or may not have covered my knee… but it was pleated! Totally screams Bais Yaakov, I knew!) Nude tights, check. Staid flats, check.

In the morning I gave myself a look in the mirror, thinking: I totally got this. I even clipped my hair back into a banana clip (remember those?), a style I noticed was worn by the frum girls in my neighborhood, which I’d gone out specially to purchase.

That Tuesday night went off without a hitch, and I fell comfortably into my routine. During the week, I wore my jean skirts and short sleeves; Tuesdays were my “JEP days,” and with it came my uniform of tzniyus skirts and Target sweaters (another ubiquitous item I noticed worn by the “other side”).

I didn’t really think much about my uniform, certainly didn’t see any contradiction in my actions. Instead, I realized that although I felt somewhat ignorant in my breadth and depth of Torah knowledge, comparatively, there was more than a fair amount I could teach the students. If I noticed a niggling sense of hypocrisy, I consoled myself with the fact that I was certainly frummer than these secular kids; if I gained extra credibility because of my dress, more power to me.

My “aha” moment came the night I was busy reaching out to participants in the program, inviting them to an upcoming shabbaton. The list included “cold calls” to gauge interest in attendance, so I was gratified when I reached a former student I had a connection with. As soon as Jessie heard who it was, she nearly yelled, “Oh, sorry!” and muffled the phone. I was confused until I noticed the background music had abruptly stopped playing.

“I’m so sorry,” Jessie said, resuming the conversation, “that probably wasn’t music you’d want to hear, so I shut it off. What’s up?”

It was sensitive and thoughtful, and I would have been incredibly touched by her understanding… had I not felt thoroughly misunderstood. For that very same CD had been blasting through my room only moments before I began my calls, inappropriate lyrics and all. For the remainder of the conversation, I was sucked into a whirl of internal confusion.

I felt called out in my act of a double life. I was honest enough to know that that music wasn’t exactly Jewish music at its finest, and I also knew I had to be a good role model. If I turned it off before I started the calls, then clearly it didn’t align with the message I was hoping to send. And if that was the case… what kind of role model was I if I was busy listening to it behind closed doors?

“Umitalmidei yoter mikulam.” Jessie saw me through a certain lens and held me up to certain standards. I was flattered — and embarrassed. Because Jessie was right: If this was how I was going to present myself, present Judaism, that type of music should offend me.

That was the last time I listened to that CD, and in its stead, I discovered the pleasure of living authentically and with emes.

(Originally featured in Family First, Issue 760)