How to Survive a Crush

Recently, I spent an evening with my high school crush. Let me clarify: I sat hiding in the audience listening to him read from his New York Times bestseller at my neighborhood bookstore in Boston. High school was 20 years ago, and I hadn’t seen this guy—I’ll call him John—since then. Showing up at the book reading seemed like a good idea at the time. Wouldn’t it be fun to see what John looked like after all these years? It’d be a hoot. Some light-hearted entertainment on a Monday night. No big deal.

As always, reality did not go according to plan. At the bookstore entrance, I was greeted by a sucker punch of anxiety: My presence there was neither fun nor funny; it was weird and uncool. And also disturbingly out of character. By most accounts, I’m sensible and sane. People know me as someone who sends out timely thank-you notes and shepherds three children to soccer and piano lessons. I teach full-time, and I’m the vice-president of the PTA. What if this guy thought that I was stalking him, or that I had nothing better to do? The fact is, I barely have time to sleep. Still, I couldn’t bring myself to leave. I settled down in the back row with my iced latte, and tried to look nonchalant.

John was wearing a more formal version of the outfit I’d last seen him in: khakis, dark blazer, studious expression. He had been a year ahead of me at the all-boys academy down the street from my co-ed prep school. Our teenage world in Washington, D.C., was a cluster of five elite institutions packed with offspring of the House and Senate, the embassies, the World Bank, and general notables around town. During high school I saw John at school mixers, parties, sports events, but never spoke more than a couple of words to him. His friends knew that I was smitten, and I felt completely ridiculous. I never knew about his family, his religion, or what he liked to read. But I did know this: He was everything I was not.

Most of my schoolmates were wealthy and pedigreed and lived in the stately homes near campus. Mine was a modest ranch across the border in Maryland.I had left public school for my private prep school in the ninth grade, joining the urbane “lifers” who had been there since pre-school. Most of my schoolmates were wealthy and pedigreed and lived in the stately homes near campus. Mine was a modest ranch across the border in Maryland. In the hallways, kids talked about regular family get-togethers with the Walter Mondales, the Bill Bradleys, and other political luminaries of the 1980s. My older, conservative parents had no connection to anything glamorous or political and could barely afford tuition for me, their only child. They were immigrants and newcomers, in every sense: I was a first-generation Jewish American in an established, blue-and-white-china private-school world. Our lack of clout pained me each of the many times I was asked: “What do your parents do?” I’d give a quick description of my father’s mid-level white-collar job at a government agency, but sometimes I told outright lies about my parents. Like that only one of them was Jewish.

My confusion was palpable. I straightened my curly hair and whittled myself thin with Marlboro Lights. I wanted so badly to be “mainstream” private school, but I also identified with the role of angry outsider. The unfortunate sartorial result of this was a cross between country club and rebel—a mishmash of Talbot’s and combat boots, topped off with scary eyeliner.

It was a time of chronic disorientation. My schoolmates’ lives were alien to me. I didn’t see my friends’ parents for months at a time. Sometimes they were traveling. Or they were just out. They did make infrequent appearances, gliding by us with a quip and a grin. They looked fantastic.

Meanwhile, I couldn’t shake my own parents. On the weekends, they frantically called my classmates to verify my whereabouts. They lurked outside of parties, adamant about giving me a ride home. They refused to let me see Lionel Richie in concert. Back at the ranch home, my mother insisted on growing the Chia Pet I received as a joke gift. My father wore “Members Only” jackets. In high school, I discovered irony and learned that my parents had none.

It was under these circumstances that I honed my Boyfriend Fantasy: a dashing preppy who would replace my “Members Only” affiliation with actual membership in the D.C. elite. He would be arch, but charming; snobby, but sweet. He would introduce me to the exquisite pleasure of belonging. His would be a world where parents were flush with funds but conveniently absent.

At the beginning of my senior year of high school, I willed the fantasy into reality, or so I thought. I ran into John, now a freshman at Georgetown, and we exchanged phone numbers. It was a two-week miracle I so desperately wanted to label “dating,” but basically it amounted to a ride in his parents’ Volvo, a shared interest in the Beastie Boys, a couple of awkward quasi-sexual interactions in his dorm room, and a trip to a sushi restaurant. Conversation involved lots of small talk and beer.

My boyfriends were foodies and oenophiles, with strong feelings about ski slopes in Vermont and bird watching on Nantucket. They refused to eat Chinese food outside of Chinatown. They wore cashmere.This thrilling, vapid relationship was so brief that John wasn’t even there for our last date. On that especially desperate afternoon, I borrowed my friend’s new Saab convertible, geared up with Ray-Bans and a good mix-tape, and headed to Georgetown. John wasn’t at his dorm, but I took the opportunity to try to impress his roommate. I offered him a ride, hoping that he would be wowed by the fancy car and tell John how cool I was. Would that I could forget my come-on: “Let’s take this puppy for a spin!” When I called John a couple of days later, he gently informed me that he was dating other girls. Presumably the type who didn’t need to impress boys by chauffeuring their roommates around in other people’s cars.

As it turned out, John was only my first foray into a more serious addiction, a gateway crush. In college, I found myself playing the part of hapless striver to the boyfriend du jour’s privileged, self-assured insider. I got to know Greenwich, Conn., and the Delta Tau Delta fraternity house. My boyfriends were foodies and oenophiles, with strong feelings about ski slopes in Vermont and bird watching on Nantucket. They refused to eat Chinese food outside of Chinatown. They wore cashmere and impossibly soft oxford shirts.

I hit rock bottom in the form of my most long-term college paramour who continuously listed the sacrifices he made by choosing me over his ex, a scion of the New York Times masthead: box seats, country club dinners, and sex in seaside vacation homes. I got over his infidelities, but his new girlfriend bothered me long after we broke up. It wasn’t just that he had been cheating on me with her; she was a Dana Hall graduate whose family brunched with Billy Joel in the Hamptons.

In the wake of my college Lothario, I faced an undeniable truth: My romantic life had taken a serious toll on my self-esteem. I had to get out of the East Coast Habitrail I’d been running in, so I made a drastic geographic decision when choosing my Ph.D. program: Wisconsin. After a summer of enduring jokes about Laverne and Shirley and Jeffrey Dahmer at Capitol Hill parties, I left for Madison, anticipating the frigid air like a spiritual disinfectant. My parents said their goodbyes as if I were leaving for outer space. They didn’t get it, but wouldn’t dare mess with anything that had to do with an advanced degree.

For me, the road to the Midwest took on the significance of a pilgrimage. I arrived with a suitcase full of books and a head full of burning shame: My past relationships were downright embarrassing, and I cringed to hear myself describe them. But in Madison, no one was judging me; the people from the Social Register were few and far between. It was as if my doctorate program also doubled as a rehabilitation center for people too insecure to thrive in elite East Coast culture. Even the people from those privileged backgrounds became something different in Wisconsin: wrapped in fleece, slurping mochas from an independent coffeehouse, getting involved with the student union. Doing their own sort of rehab.

It wasn’t until I was surrounded by smart, charming, good-looking people from diverse backgrounds that I realized how shallow and myopic I’d been. Free from the mental burden of trying to fit into the D.C. upper-middle class, I could completely let loose. I learned to cook and how to live on five dollars a day. I let my curls go wild and bonded with people from all walks of life. Single for the first time in years, I dated all sorts of men: the Brad Pitt-lookalike from the bike shop, the angry lapsed Catholic from Ohio, an identical twin from La Crosse who had never been on an airplane. I hung out with the lead singer of “Poopshovel.” Life was poetic and full of revelations. I bought the car of my prep-school fantasies—an old Volvo which, like a heavy-handed metaphor, met its end in a giant, Wisconsin-style snowstorm.

My real hope that night was to put the old social wannabe me to rest. My glorious evolution over the last two decades into a mature and confident person would be on full display!After a few years in Wisconsin, I even fell in love—with Marc, who shared my immigrant family background and ranch-home childhood, but not my insecurities. It never crossed his mind to be intimidated by anyone; he was a smarter, better version of me. Marc was the first boyfriend to make a strong impression on my parents; they had always kept quiet about my love life, but now they couldn’t contain their excitement. They didn’t even realize that there were other Jews in Wisconsin. Marc and I graduated, got engaged, and accepted jobs on the East Coast without a moment’s hesitation. I missed my family and my old friends and needed to go to a place that felt more like, well, home. I was ready to come back.

Even though everything has fallen into place over the last several years—a happy marriage, thriving careers, a brood of great kids—seeing John standing at the podium in all of his sangfroid glory reminded me of why it’s not always easy to come home again. How much had I really evolved? Twenty years after the Saab joyride, I was spending a Monday night staring at this person. D.C. private school life was long gone, more than a safe arm’s length from Boston, but maybe I still craved its approval.

As a masochistic exercise in this regard, John’s book did not disappoint. His subject matter led him into detailed explications of privileged life: wine tastings, private art collections, public squabbles over family fortunes, and the like. He was droll and completely at ease in the spotlight. I responded with the crowd at the right moments, feeling my curls start to frizz.

After the reading, I waited in line to talk to John. My real hope that night was to put the old social wannabe me to rest, once and for all, by confronting the person who saw me at my lamest. My glorious evolution over the last two decades into a mature and confident person would be on full display! Wasn’t that why some higher power—one that had my back—had ensured that John would be a sitting duck for a designated period of time just two blocks from my house?

Evidently not. When it was my turn to talk to John, I noticed my chewed-up straw protruding from my empty latte cup like a dipstick gauge of my mental state: macerated, spastic, out of place. John had no idea who I was at first. But when I said my name, there was immediate recognition and then a look of . . . fear? Sympathy? It was so awkward that I got dizzy. Still, I pressed on, yapping away about the details of my life, determined to prove that I was not a loser. John was polite and gracious. And a complete stranger. Trying to impress him was like taking a deep drag from the cigarettes I quit a long time ago: a familiar, nasty little habit.

I left the store feeling stupid but nostalgic. Sure, it’s a great thing that I’m no longer that pretentious striver. But in trying to reform the lame girl I was, I underestimated her charms: She was always daring and goofy in a truly intimidating set of circumstances. She was raw and real, and wore her vulnerability on her sleeve. No one depended on her to have it all together. She was the kind of girl who’d show up at some guy’s book reading, totally uninvited.