Growing up Orthodox, everything I learned about women came from my non-Jewish driving teacher and old episodes of The Fresh Prince of Bel Air.

And then, I met her.

I was 27, and she was my first non-orthodox woman. For her, I made an exception, broke the rules I’d been raised with. She was a camp counselor at a vegan, LGBT-friendly overnight camp. She worked at a museum and spoke Yiddish. She’d learned it in college, which to me was way cooler than the kind my Hasidic neighbors spoke at home. She was someone my Orthodox Jewish parents in Brooklyn wouldn’t approve of, which was still the first thing I worried about when it came to dating.

We met a few times at different Jewish social things, from a Hanukkah-themed open mic at a local bar to eating bagels with her friend, my sister. Even though I am, at best, agnostic about klezmer music, when she mentioned that she liked klezmer, as we munched on kosher lox in the East Village, I found myself exclaiming “Me too!” She invited me to a concert/jam session in a friend’s basement. Over Facebook Messenger, I asked her if she wanted to upgrade it a date, a move befitting men much smoother than me. She said yes. Will Smith would have been proud. My sweaty palms rested on the keyboard triumphantly.

But she was secular and I was observant. She watched Fiddler on the Roof; I was Fiddler on the Roof. Still, I liked her a lot. I wanted to make it work. Dating her meant dating up. She was worldly, cultured, and funny. I was not.

She smiled when we met outside the Brooklyn house where the klezmer concert took place. We sat cross-legged on the carpeted floor in the unfinished basement as music played. I shared my water bottle with her. It was a tiny moment of intimacy. Later, she leaned over and put her head on my shoulders. Her body tilted into mine, and she swayed back and forth with the music.

According to the TV and movies I watched as a kid, this was progress. As we waited in the station for our trains to take us to different boroughs, hers to Queens and mine deeper into Brooklyn, we chatted until there was an awkward moment, the first of the evening. As I’d learned from my on-screen heroes, this was the time to kiss her, only the second kiss of my life. I wanted it, even if I was terrified. I leaned in. She, the more urbane one, took the lead. Following was a natural fit for me. I didn’t quite know what French kissing was, but this was definitely European.

And then I tasted the faint taste of cheese crackers. On her tongue. Cheese crackers. Observant Jews don’t have any dairy products for six hours after eating meat, and I’d had a burger before our date. Was this considered mixing meat and dairy? Was I allowed to do this? It was problematic enough that I was kissing her, but this seemed beyond the pale. No longer able to savor the fantasy, I came crashing down back to earth.

I was anxious. I started sweating more profusely. Should I stop kissing her? What would I say? Would that be rude? I already had mixed feelings about kissing her, because I grew up shomer negeia, not touching the opposite sex. Was I throwing this all away after more than two decades of good behavior? Would I hurt her feelings by ending the embrace mid-moment? After we went up for air a few times, my train came and saved me from my thoughts. We quickly said goodnight, and I rushed into the solace of the closing train doors.

As I wiped off the remnants of our romance from my lips, feelings of intimacy were replaced with regret. What had I done? How could I get myself involved with someone I could not end up with? There was no way I could marry her. What was I doing?

For days, my mind raced. I couldn’t stop thinking about what I had done, about what it meant. Then, we met for a second time for coffee. I was comfortable then, sitting in oversized seats, drinking coffee at a café with board games. The comfort came from her, not the chairs. I acted natural, hiding my turmoil. She then invited me to a café near her place in Astoria for a folk-music singalong.

This soothed me. Growing up, I sang the traditional Hebrew and Yiddish songs every Shabbat, but also folks songs and tunes by Bob Dylan, Pete Seeger, and Phil Ochs, a merging of the secular world and the religious one. Just like me and her, I thought. Maybe it could work after all.

The cafe was near her house, and I was anxious that she’d invite me over afterward. I had to be prepared. Did I need condoms? I didn’t know how to use them or where to get them.

As we walked in, I felt a warm feeling of nostalgia coming from the old people singing the Woody Guthrie song “Pretty Boy Floyd.” We whispered to each other, and her face was lit up by the candle on the table. For three hours, we didn’t say much, just listened to the music, enjoyed being with each other. We left as men and women sang “Deportees.”

As we walked back to the train and she held onto my scratchy tweed-clad arm, I felt a heaviness in my bag. After attending the daily morning prayers at a nearby synagogue, I had studied Jewish texts with some of the members. Each day, one of us prepared a lecture to give to the group. The next day was mine, so I had the book with me to prepare.

As I walked to the train with her on my left arm and the holy book in my right, I felt pulled in opposite directions. Was I the guy who woke up at an ungodly hour each morning to pray and study ancient texts, or was I the person who dates women casually? Where do my values lie? As we slowly walked to the train, I realized I had to break up with her. Gun to my head, I was the guy with the Hebrew book of Jewish law weighing me down.

We sat on benches in the frigid evening and I tried to make it clear that it wasn’t her. I remembered the “It’s not you it’s me” routine from Seinfeld—except I was earnest. It really was me. Soon, the cold February air sent us indoors, our relationship ending where it first began: At a subway station. After talking for two hours, I got on my train as she wiped away tears. She kissed me one last time on the cheek, with permission. It killed me to hurt her. As I transferred to another train at Times Square and rode an escalator up, I saw another couple on the escalator going down, making out.

I now only date observant women. But every time her name pops up on my Facebook wall, my heart skips a beat. For a second, I re-calculate the mental math, trying to make it work. We still hang out, not infrequently, enough though it hurts: At friends’ parties, at protests, at all sorts of Jew-ish, but not Jewish, events. But it’s not the same. We could have been that couple I saw at the subway station that night, kissing happily, with nothing to separate them from each other.





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