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How I Stay Single and Sane While All My Friends Are in Relationships

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Photo by Collin Orcutt

On a recent visit to Washington, D.C., I stayed overnight with one of my closest friends and her boyfriend. Karen and Ben* had moved in together a few months before, and it was the first time I was seeing their new place — their tiny indoor herb garden, the giant television cabinet they’d built together, the shared bedroom closet overflowing with suit jackets and frilly dresses. True, they’d been together since college, but back then it all seemed like playing house, not the same kind of relationship that my mother and father or other “real” adults had.

Lying on the pullout couch that night, I wondered when exactly it had happened. When had everyone else turned into those real adults, with real lives and real relationships and real plans for the future, shedding the shape of undergrads who stayed up too late and used “points” to purchase meals in the dining hall?

It wasn’t just Karen and Ben. Over the past few months, I’d watched nearly every close friend of mine enter a serious (or at least semi-serious) relationship. I cringed each time I logged onto Facebook, where an inevitable procession of wedding photos and engagement announcements (OMG so excited 4 u!!!) made my own life accomplishments (did my laundry for the first time in three weeks!) seem vaguely ridiculous. Where I once daydreamed about seeing my byline on the cover of a bestselling novel, I now alternated between wedding-day fantasies and nightmares featuring lots of cats. Suddenly it seemed as though the world had gotten smaller, and my sole occupation was searching for a suitable mate while trying to hold onto my dignity.

One is the Loneliest Number — The Only Single Standing

I was 24 years old, and on some days I felt as though I were plagued by jealousy and misanthropic thoughts every time I passed a happy couple on the street. On a rational level, I knew I had a life many women my age would kill for: a job that I loved, an apartment in New York City, a ton of loyal girlfriends. From a practical standpoint, a boyfriend didn’t really fit into my lifestyle: I worked a lot, caught up with friends on the weekend, and needed at least an hour of quiet novel-reading a day to stay sane. I was a happy woman.

But I was also a single woman. And although that hadn’t ever bothered me before, a human tendency to compare myself to similar people — friends, family, coworkers ­— meant that it bothered me now. My mother was 24 when she met my father, 26 when they got engaged. Nothing about my current romantic life gave me hope that one day soon I too might be in a long-term relationship. There was the tall Israeli man who stopped returning my texts after we’d been dating for about a month. The medical student I met at a Shabbat dinner who was supposedly still pining for his last girlfriend. The filmmaker who still texts, but only on Saturday nights, to ask if I want to “hang out.” (I don’t.)

None of these unfortunate circumstances would have been especially troubling if I didn’t feel like I was the only single girl left on the planet. One day I made a list of absolutely everyone I knew in my age bracket who was in a committed relationship (62), and everyone who was still single (13, plus me). I panicked.

On the Prowl — Attempts to Leave Singledom

For the first time in my life, I actually wanted a boyfriend — not a specific guy who charmed me with his smile and the way he held my hand, but any dude who was willing to call me his girlfriend, just for the sake of saying I was “attached.” It was less about the way I saw myself, and more about the way I thought other people saw me. When my roommate introduced me to her new boyfriend, did he wonder why I couldn’t do the same? Did they feel pity, snickering at the idea of me lounging in sweatpants and eating sorbet from the container on a Saturday night? In all likelihood, they couldn’t care less about my weekend attire — but my insecurities about romance had slowly started to wear on the self-confidence I’d developed in the years since high school graduation. Beauty may be in the eye of the beholder, but something happens to your ego when seemingly everyone’s being behold-ed except you. 

So I took action. I joined JDate. At night I scrolled through rows of punny usernames and snapshots of pets, searching for someone I could bring to dinner with my friends. I looked for guys who were smart and witty and guys who resembled my last boyfriend, and avoided responding to generic messages asking about my weekend. I met a guy from Queens who seemed sweet, but who laughed out loud when I told him I was a vegetarian and made a weird reference to anal sex in the middle of conversation.

At some point, even my parents started to sense my desperation. My mother told me that my father had been querying his coworkers about potential single sons. I was humiliated. They’d worked hard to raise a girl who was self-sufficient, a woman who knew her own worth, and the fact that I was looking for a boyfriend as an extracurricular activity made me feel as if I’d lost sight of those values.

Still, I continued my search, albeit more quietly. One night, my phone buzzed incessantly with incoming messages from a writer I’d met on JDate, a voicemail from a lawyer my dad had tried to set me up with, and an email from my friend Karen about my romantic escapades. I was sitting on the couch reading “Middlesex,” a novel that’s partly about a brother and sister who marry each other, and feeling better about the fact that at least someone’s romantic life was more pathetic than mine. The writer wanted to know if I was free this Saturday; the lawyer, this Sunday. Immediately, I started responding in a flurry of excitement, typing away to let each one know I’d be away this weekend but would absolutely love to get together some other time. Was I really in a position to discourage anyone’s interest?

And then I put the phone down. I started to laugh, even though nothing was especially funny. I’d been waiting — so long, it seemed — for something to happen. For someone to profess his undying love for me. Or for disco diva Chaka Kahn to show up and tell me I didn’t need a man because, alas, it was all in me. But maybe something had already happened. Maybe this experience — of feeling alone and different and never quite at ease — was something important that would shape the way I acted in the future, whether single or in a relationship. Maybe it was okay not to be completely content. Maybe life was actually more meaningful when I wasn’t.

*Names have been changed.

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I'm the senior writer at Greatist, and I mainly cover new trends in psychology and mental health. When I'm not hanging out at Greatist HQ,... Read More »