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When I first signed up for online dating in the early 2010s, I was fairly sure it would work. Sure, there would be lots of bad dates. It would feel hopeless! But then I’d meet a guy with a sweet smile who’s nice to talk to, and I’d never date again.
Joining Match.com seemed out of the question. To me, it felt like a sea of bearded schlubs who were constantly explaining wine tannins or suggesting we go listen to their Pandora jazz station. Not only was Match distinctly uncool to 25-year-old me, but it felt expensive. Back then, the only website I’d ever given a credit card to was Netflix for the DVDs I never watched.
In contrast, OkCupid.com was the website the Village Voice had called “a favorite hangout for internet goers.” Like me! Their landing page featured a cartoon lady who looked like Lisa Loeb without the glasses. Smart and sexy? Like me! When my desired username was taken, OkCupid offered suggestions for how to make it more distinctive. “How about we add “taco” or “tron” to your name?” Sure, I guess! OkCupid felt like my sweet dorky friend who sincerely wanted to help me to find a boyfriend.
I wanted my dating profile to suggest I was someone clever who was also incredibly good at sex. For my bio, I plagiarized Kim Jong-Il’s Wikipedia page:
Born in a log cabin in Mount Paektu; birth was foretold by a swallow, and heralded by the appearance of a double rainbow across the sky; shot 38-under-par first time playing golf; invented the hamburger.
I wanted to seem like the kind of girl Cake songs were written about. Under hobbies I wrote: “Telling stories, wearing skirts, talking to strangers, making my own salad dressing, finishing off a bottle of wine, and leaping out of moving vehicles.”
To be clear, I’ve only leapt out of a moving vehicle once, and it was to avoid an ex-boyfriend. He was the first person to ever tell me about OkCupid, in the context of how much he missed using it. In fact, in my 20s, I found that all of my boyfriends seemed to love online dating. Over G-chat, B. told me he’d met his future wife on Match.com, despite his unfortunate username “theasianmacgyver.” My friend D. met his girlfriend by sorting through every profile that mentioned “NPR.” His username? “DrivewayMoment.”
But soon I realized it wasn’t going to be as easy for me. At first I was thrilled by how many messages I was getting. Then I read them. There was, “Are you jewish? You seem jewish.” And, possibly related, “I like your nose. lets [sic] have sex.” One aspiring comedian, after reading that I’m a journalist, said, “Hey girl. I bet that article deadline isn’t the only thing that’s flexible.” Despite OkCupid’s geeky twee sweetheart brand, the reality of what I experienced on that website felt like it was coming from a dark corner of the internet I’d never explored before. I’d been prepared to complain about things like missing apostrophes and blurry bathroom selfies in dating profiles. I wasn’t prepared for it to feel like my own personal game of Fear Factor: in order to win your prize, you have to endure something gross that goes against your every instinct to run.
I treated the harassment like the price of admission for online dating. When my friends quit apps because of things like “too many murder jokes” and “I saw my boss on there,” I felt proud of my womanly ability to endure shitty things. Plus, I was developing an incredible skill for spotting the nice guys, and convincing them to date me. OkCupid is where I met S. with the fixed gear bicycle, who ended things because I seemed to care too much about sex. (I did.) It was where I met the cartoonist M., who didn’t own a second pillow so I gave him mine as a breakup gift.
It felt like my own personal game of Fear Factor: in order to win, you have to endure something gross that goes against your every instinct to run.
I’d started my online dating journey hoping to meet someone who would want to enter adulthood with me. But while I was working on my 5-year plan, I’d meet guys who were still getting the hang of remembering to drink water. As I approached my 30th birthday, I began to worry that I’d wasted my best single years online dating. I’d lie in bed, noticing the missing body next to mine, and Googling, “Did I miss my sexual peak?”
That changed after I downloaded Tinder on my iPhone 3. Right away, I felt like I’d been born to date using my phone. Decision-making with my thumbs gave me a sense of control in a situation where I’d previously felt powerless. I quickly swapped my long, involved OkCupid profile for the short Tinder bio: “Marry me for my dog.”
Within a few weeks, I couldn’t go to a bar without noticing everyone my age swiping alongside me. At last, my married friends were jealous of what they’d missed. They’d watch over my shoulder as I’d rapidly swipe left at the first sight of a topless gym selfie, and pivot right for an adorable puppy. I’d swipe left on a man-bun, right on a top fade, left on a drugged-tiger selfie, and right on the guy I kinda knew in college.
By then, I’d developed some important dating skills. I learned how to endear myself to bartenders for safety, how to switch to seltzer after two drinks, and how to keep a secret tally to make sure I wasn’t the only one making me laugh.
I learned to ask myself important questions like, “How do I really feel about adults who pay for improv?” Most importantly, I learned how to end a date after the first glimmer of unexamined misogyny, like the time a writer told me his philosophy about NYC dating: “The odds are good, but the goods are odd.” I walked right out of the bar, having already paid for my drink before he’d arrived.
I learned to ask myself important questions like, “How do I really feel about adults who pay for improv?”
In 2014, I met someone on an app. He was tall and bald, with a gap between his front teeth. He read fiction for pleasure. When we went to the beach, he’d kiss my salty naked shoulders and ask, “How’d I get so lucky?” It was our 2-year anniversary dinner, while we waited for dessert, when he casually said, “I’ve been thinking about it, and I never want to have kids.”
Dating had taught me a lot about first impressions, but absolutely nothing about navigating difficult relationship conversations. I knew only how to avoid questions that could lead to a breakup, and the kid decision was one of those things. Weeks after I moved out of our shared apartment, we were both back on Tinder. His new profile included a photo of me, with my head cropped out of frame.
Going back to online dating in 2016 felt like moving home after college. So many familiar faces I never wanted to see again. Tinder was such a breakthrough success in the online dating space that a million copycat apps had bloomed, each with its own gimmick. I signed up for Bumble, Hinge, The League, Coffee Meets Bagel, Hater, Happn, Jswipe, Feeld and Raya.
The dating app boom gave me endless possibilities for how to meet someone, while also making it harder for me to actually meet them. I’d often match with someone exciting, and then completely forget to reply to their messages because I was busy checking another dating app. In my phone contacts, I started organizing my dates by assigning them a last name according to the dating app where we met. There was G. Hinge, who refused to kiss me in public, and K. Raya, who asked if he could “get me off” on our walk to my car. D. Bumble had the horrible luck of going on a date with me immediately after W. Tinder ghosted me. All he did was ask about my week, and I started uncontrollably crying in the middle of a beer garden. Online dating was starting to feel like a hellish Groundhog Day curse with no end in sight.
I often wonder if I made a mistake leaving my love life in the hands of technology companies for so long. Why did I so willingly trust that these apps were invested in helping me find a partner if their success is measured in monthly active users? If I weren’t single, they wouldn’t have me around to participate in their interactive advertising campaigns and to purchase premium membership features.
In so many ways, I feel better at dating now than I’ve ever been. When I’m swiping, I’ve learned how to slow down and ask myself better questions to direct my thumbs. To gauge attraction, I ask myself, “If this guy was your neighbor, would you come up with creative ways to talk to him?” To gage social compatibility: “Can I picture myself in all of these photos standing next to him?” On especially hard days, I slow down and try to find just one thing to love about each profile (an idea I got from Lori Gottleib’s book Marry Him).
On a recent first date in LA, in the back of dark French cocktail bar, N. Raya told me he had an idea. “You know what I like to do when I’m feeling the melancholy of my mid-30s? I like to drive down Sunset Boulevard from beginning to end, all the way to the ocean. You know, watch the city through my windshield like a movie.” He lifted his eyebrows and grabbed my hand, “What if we get out of here, right now, and go for a drive?” The idea was so wildly romantic! I instantly hated it, and wasn’t afraid to tell him that.
In ten years, the biggest thing that’s changed in my dating life is how I define romance. My favorite dates now involve long conversations about how it feels to still be single when most of your friends are married. I swooned over the guy who told me my Costco membership was turning him on. I was instantly seduced by the guy who checked with me after our third date to make sure I’d be okay with annual trips to Disney World if we had kids. I have no idea what my future love life will look like. But I said sure.
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