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“50 First Dates”: Learning About Love After Modern Orthodoxy

My first real grown-up date, when I was 20, was an absolute calamity. Before agreeing to go, I had what felt like a 40-minute panic attack. “How do you expect to ever find a husband if you’re scared of a coffee date?” asked my Mom. She was right.

I was a ball of utter chaos: Was I supposed to offer to pay? What would happen at the end of the date? What was I supposed wear? What is dating? As we walked into the coffee shop, I tripped for no apparent reason. A kid laughed. Later, my date—a tall, dark, handsome Jewish law student—drove me through a cemetery. We did not go out a second time.

A lot of people are nervous on first dates, but I seem to experience excessive anxiety—or at least, I used to. Why? Because I grew up Modern Orthodox. I attended a yeshiva where there was no opportunity, really, for boys and girls to learn about the secular dating world. My school was co-ed, but it didn’t help the matter. Following halacha, the school’s message about was sex was firm: none of it before marriage. One of the main administrative goals each day was to  keep boys and girls away from each other.

Modern Orthodoxy is kind of a gray area, encompassing was wide range of religious practice. When people ask about my parents’ practic, I hesitate about how to describe them. They keep Shabbat, but my mother wears pants, and they eat vegetarian food at non-kosher restaurants. Some members of my extended family who also call themselves Modern Orthodox are strictly kosher, and cover their hair after marriage. Most Modern Orthodox people venture into the secular world for study and work, but many only socialize with other Orthodox Jews. The level of familiarity with pop culture varies greatly from family to family and person to person.

The messages we received in my community about dating were confusing. Only certain activities were acceptable, and the rules seemed arbitrary. “Dating” meant that you walked to class together and maybe went over to their house for Shabbat lunch. My first boyfriend—who I ogled for three years before we actually started hanging out—lasted all of two weeks. We rode our bikes and sometimes sat next to each other when the whole gang went to the movies. Romantic. As far as the physical aspects of the relationship, hugging was about as far as it went. Maybe the occasional touching of the elbow. No hand-holding and certainly no kissing. It wasn’t just us.

When I was 15, a friend told the entire neighborhood that I was a whore because I sat next to a boy on a shul trip to Hersheypark. I was comfortable hanging out with boys in a friendly, platonic context, but unfortunately, some people in my Modern Orthodox neighborhood did not feel the same. (That same “friend” later got sprung sneaking out with boys, which led to some difficulties getting into seminary. The neighborhood covered for her.)

Every love connection I had was accidental. When you grow up together, you just get thrown together. You don’t date in a traditional sense, you simply hang out closer, with an almost imperceptible increase in frequency.

My first “real” relationship started just before eleventh grade, with a guy whose religious observance swung from eating at Olive Garden and making out with girls, to Orthodoxy, to some variation of the two. The first and only time he spent a weekend at my house, he showed up with a giant black hat that he had spent too much money on, which scared my parents, who wanted me to be observant, but wanted to make sure I stayed true to my own beliefs. With him, I got a taste of almost every type of Judaism.  I thought it would broaden my relationship horizons, that I wouldn’t be so scared of guys and dating. It didn’t. He was the first guy that I had any sort of physical relationship with. Most of that had to do with the fact that he was from a different community and wasn’t raised Modern Orthodox.  When I started dating him I kept most things from my friends, but a few warned me that being with someone who wasn’t religious was a bad idea.

Once I left the bubble of yeshiva and found my footing in the secular world of college and dorms and parties, I realized that those other folks in my community—the ones who attended Orthodox, single-sex high schools—had it easy. My friends whose schools were more Orthodox than Modern were having an easier go at college life because all they went to the same schools (Queens, Stern, YU), never completely leaving the bubble. They dated within their community, with people who had the same level of romantic experience and the same expectations. Their rules of dating were clearly delineated. Most of them are married now. I was the one with the problem: I was dipping my feet in dating pools beyond my depth, with people who were far more experienced and comfortable than me.

In my freshman year of college, my sculpture TA caught my eye. He walked into the studio with his newsboy cap and glasses, making me want to marry him. I lost all motor skills each time he approached my table. Once I accidentally smashed my little statue. My friend Sammi would stand next to me molding her clay and I’d nudge her, asking “What do I do?” The semester was grueling and I was in jeopardy of not finishing my final work of ‘art.’ The closest I got to flirting with him was lying to him about liking to fish. (I saw it on an episode of Gilmore Girls.)

When the semester ended and we all went home for the summer, my big move was sending the TA a Facebook message confessing that I had a big-league crush on him—something a sixteen-year-old might do. Needless to say, the relationship never blossomed, though we did stay in touch.

My yeshiva left me with a pretty solid education, but almost no life skills. It wasn’t until I was nearly done with college that I started to feel at ease in the world of dating, and that was because I decided to work on an ethnography-type thing about the culture of online dating for credit. I actually picked dating as my writing project for the semester so that I’d be forced to learn how to go on a date.

And so, I went on dates. Many dates. I became a student of flirting, plate-sharing, coy glances, teasing. Each dinner or seat at a bar taught me something new. I learned that people who have been dating since they were 14 still get nervous. One of my first dates couldn’t seem to remember the college he went to. Another spilled beer all over the bar counter. And more than a few of them, jittery and clumsy, confessed to me that they were “a bit nervous.” So if I didn’t know how to answer a question or if I spilled my drink or tripped (which happened a lot), it was okay. More importantly, it was pure immersion therapy: the more I pushed myself, the more comfortable I became. After a while I stopped walking into glass doors. Making conversation became much easier. One guy even called me a good “verbal-spatting partner,” which I considered a win.

About three years after I confessed my crush to the TA, he messaged me on Facebook and asked me out. Butterflies were swing-dancing in my stomach, but I kept my cool and it went well. I accidentally called him by a codename Sammi and I had given him, but I covered it up with a cough and a smile. I didn’t feel uncomfortable and I didn’t feel as though I was playing dating catch-up. I felt normal. We didn’t get together, but I finally felt as though I had finally graduated into the adult world of dating.

There were many awkward moments along the way, but I think I have finally leveled off with my peers in the school of love. I am more comfortable now. Not confident all the time, but not frightened whenever I have to talk to a guy.  I’ve found someone to be with who, I think, would be surprised to know what a disaster I used to be. I’ve spoken to a lot of people who grew up in communities similar to mine, and learned that we all share a common naïveté when it comes to the world of secular dating.  But everyone has their ‘thing,’ no? Every person goes into a relationship with baggage or quirks or expectations—so it’s a process of consciously keeping those neuroses in check and not letting them hinder the progression of a relationship (or even that one date). There’s no formula to what works, it’s just a process of trial and error until you one day realize “Hey, this ain’t so bad.”

Daniella Bondar is a MFA Creative Writing Nonfiction student at The New School. Wandering New Yorker. Insomniac. She’s working on a memoir about her gold dress phobia. Follow her on twitter and find her writing at

(Image: Shutterstock)

Related: I Hid My Non-Jewish Boyfriend From My Family For Over A Year

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