The Links guide to online dating

From "internet personals" and love hackers to fuckboys and Tinderellas

The first picture I have of Jason and I, about three weeks after we met.

My introduction to my husband Jason was less a meet-cute¹ than a meet-sleazy. The year was 2012 — I was 22 years old — and my brief, wild foray into online dating had already proved a bit choppy.

I’d gotten beers with a fact checker for The New Yorker who never texted or called me again. I’d had coffee with various self-satisfied lawyers whose professional monologues challenged my considerable powers of attention. I had one very memorable date with a 30-something-year-old programmer who revealed, about two hours and several cranberry-vodkas in, that he and his girlfriend — shock! scandal! — were actually looking for a third. (You’ll have to pay me more than $7 to hear how that date concluded.) 

The evening that I met Jason, though, represented a sort of dark nadir. While getting ready to go out to a bar in D.C. with my friends, I received an unsolicited dick pic: flash-on and flaccid, if memory serves, and from a guy I hadn’t even slept with. 

The dick pic enraged and deflated me: Why, I moaned, passing the picture around the bar, were men on OkCupid so fucking dumb? I complained so bitterly and so loudly that a sympathetic older couple bought my friends and I a round of tequila shots. Everything would get better with time, they assured us. We just had to be patient.

But I wasn’t patient — I was 22! I hardly knew the word. So instead of thanking this generous couple for their Patrón and their wisdom, I drunkenly sneaked off to the bathroom. There, I texted an OkCupid prospect who had flaked on two previous dates. This one was not a keeper, my friends and I agreed, but the tequila made me reckless and a bit lonely.

If you still want to meet me, I tapped, THIS will be your VERY LAST CHANCE. Jason, to his credit, obligingly dragged his ass to Churchkey from the comfort of his apartment.

Neither of us guessed that would be it; that we’d later have to sanitize the story of this meeting for our respective moms. But that’s online dating, I’ve always thought: random and chaotic and terrible and weird and then — with time or patience — transformative.

In the years since I met Jason, many of our friends have also met their partners through OkCupid or the swipe-based apps that followed. According to the Pew Research Center, roughly one in 10 partnered adults met their significant other online, a figure that rises sharply for young and LGBTQ people.

At the same time, there’s a growing narrative that Tinder and its ilk have degraded, while also fostering a new dating culture that is in turns dehumanizing, disposable and exploitative. In that same Pew survey, 46% of online daters characterized their experiences as somewhat or very negative. Today’s 22-year-olds purportedly pine for the era before apps; some daters, desperate for alternatives, have turned to in-person speed-dating or other, unromantic online venues.

Just last week, The Cut published a widely circulated story headlined “Is Dating a Total Nightmare for You Right Now?” So many women answered in the affirmative that the site then published a follow-up with their responses.

Has online dating actually gotten worse over time? Or have people gotten worse? Or — *gestures vaguely* — something else? My experience on this front ended 12 years ago, so when I set out to compile this latest Links Reading Guide™ I cast a very wide net. I wanted essays that captured the evolving chaos and charisma of online dating over the past 20 years. I wanted features that explained how these tools work and what their creators were thinking when they made them. And I wanted pieces that captured something timeless about the way people connect (or collide) on the internet.

“Making and posting a profile is an act of faith,” the novelist Jennifer Egan wrote 21 years ago, in a piece that also chronicles the very modern menaces of serial fuckboys, flakes and ghosts.² 

This is the third in a series of monthly round-ups where I dig into the archives to bring you the best reading around a given theme or topic. The first two concerned internet-infamous personal essays and the teenage screentime panic.

As always, please alert me to any great stories I missed or overlooked. I try to make these absurdly comprehensive — I’ve read at least 100 dating articles in the past few weeks, just working through keyword searches on major news sites and sifting through years-old #longreads on Twitter — but “comprehensive” is a fantasy online, so I value your suggestions.

🌟 CLICK HERE to view all 13 links in a quick, clickable format.🌟

The Links Guide to Online Dating

“Love in the Time of No Time,” by Jennifer Egan for The New York Times Magazine (November 2003). I love this piece as a time capsule, as an anthropological study of early aughts online life and as a demonstration that many of the problems “caused” by dating apps actually pre-existed their invention. (Journalists of every era, it turns out, have been able to locate slutty, noncommittal dudes willing to brag about their exploits under a pseudonym.) At the same time, despite documented drawbacks and lingering stigma, early online daters felt tremendous possibility and hope. It’s honestly a bit lovely and wistful, the way Egan describes this new frontier: “This is how the Internet was supposed to work.”

“How Do I Love Thee?” by Lori Gottlieb for The Atlantic (February 2006). The notion that anthropologists, data scientists and other credentialed experts once sweated the scientific rigor of online matches feels profoundly quaint in an era when most apps merely pair you with a warm body near your present location. And yet! That was the beguiling premise of eHarmony, Chemistry, OkCupid and other early-aughts start-ups, which claimed their mysterious matching algorithms could reliably find “the one.” This has since emerged as near-total bullshit … though some early proponents of the science-algorithm theory still maintain the validity of their methods.

“The Love Techs,” by Kevin Alexander for Boston Magazine (January 2008). A vivid early profile of OkCupid and its founders that made me laugh out loud on two separate fronts: inadvertently, through its comically dated characterizations of mid-aughts tech and culture (Boston is the “techiest city in America”; trendy men are “Urban Outfitted frat bros”) and more deliberately, through its colorful descriptions of emergent online dating rituals.³ About two-thirds of the way through, Sam Yagan — OkCupid’s then-CEO — also makes a distinction between types of dating apps that still feels pretty salient now:

“It helps to know the difference between ‘transaction’ sites and ‘destination’ sites. Typical online dating services qualify as the former. Think of them as supermarkets: They want you to come in, find what you need (a date, ideally), and, as long as you’ve paid, get out. OkCupid, however, is a destination site … OkCupid has to not only get you to its URL, it also has to keep you there, clicking around.”

“The World of Internet Dating and Mating,” by Nick Paumgarten for The New Yorker (June 2011). At almost 11,000 words, this is probably as close as you can get to a comprehensive early history of online dating, from the advent of “Technical Automated Compatibility Testing” in 1965 to the height of Match and OkCupid four decades later.

“A Million First Dates,” by Dan Slater for The Atlantic (January 2013). Slater, who later expanded this viral feature into a book of the same name, was perhaps the loudest early voice warning against the antisocial effects of online dating. His central premise — that dating apps would dent, if not destroy, the allure of monogamy — was fairly controversial even at the time, and remains unproven now. Then again … a growing number of young people, in particular, do say they’d prefer a relationship that doesn’t presume one primary partner.

“How a Math Genius Hacked OkCupid to Find True Love,” by Kevin Poulsen for Wired (January 2014). Chris McKinlay, then a 35-year-old mathematician at UCLA, scraped thousands of OkCupid profiles to reverse-engineer ~what women want~, then tweaked his own profile to juice his heretofore lackluster dating prospects. This story is framed like a fun nerd caper; I think we’re supposed to cheer for McKinlay as he logs and annotates and “optimizes” his way through 88 (!) first dates. But that type of ruthless, mechanical strategy now looks a lot less sympathetic — and a lot more manipulative — than it did in 2014. Incidentally, I could find no immediate evidence that McKinlay married the woman to which he proposed at the end of this story.

“Matchmaker, Matchmaker, Make Me A Spreadsheet,” by Chadwick Matlin for FiveThirthyEight (September 2014). Much like OkCupid, FiveThirtyEight thrived in a naive, optimistic era when “big data” appeared to hold profound predictive and sociological potential. As Matlin discovers here, however, OkCupid’s grand, data-backed insights into human nature — which regularly went viral in the early 2010s — often weren't terribly meaningful, and sometimes were pretty stupid. Alas, FiveThirtyEight only learned that lesson after the 2016 election, which further proved the limits of “data” in all its messiness.

“Tinder and the Dawn of the ‘Dating Apocalypse,’” by Nancy Jo Sales for Vanity Fair (August 2015). This slightly hysterical, blockbuster account of 20-something fuckboys and “Tinderellas” risked Tinder’s reputation to such an extent that the company’s official Twitter account posted a 30-tweet screed about it. Admittedly, a lot of these anecdotes feel fake or forced to me: Was every 20-something swiping at the bar? Did the boastful banker really bag five women in one week? Regardless, this story drove the discourse (and the moral panic) around dating apps and hookup culture for years to come; Sales herself got a book out of it on her personal experience with Tinder.

“Mr. (Swipe) Right?,” by Nellie Bowles for California Sunday (January 2016). A disillusioned early Tinder employee told Bowles “the app reflects the personality” of its founder, Sean Rad; if that’s true, then it makes sense to understand him better (… though he stepped down as Tinder’s CEO less than a year after this profile published). It’s a humanizing — maybe rehabilitating? — portrait, and Rad comes across as a well-meaning man-child, though a man-child nonetheless. Instagram would suggest he has since grown up and settled down (in a GORGEOUS house in LA, holy shit) though Tinder perhaps hasn’t.

“Pilgrim at Tinder Creek,” by Andrew Kay for The Point (February 2017). I began reading this 10,000-word essay just before 11 p.m., figuring I’d get a sense of it and pick things up in the morning. But reader: I was riveted. This piece is gorgeously, stunningly written — not unsurprisingly, by a Ph.D. in literature — who finds himself simultaneously navigating the roiled waters of both Tinder and the academic job market.

I kept hoping for some measure of the commitment that seemed, whether in love or work, like the precondition for a pleasure that could be redemptive. I didn’t want to accept a view of life as an archipelago of isolated encounters, or accede to the logic—reinforced by the utility-driven instruments colonizing our lives—that people mattered for their short-term use value. Still, I saw that as Tinder and other apps became an integral component in the new sharing economy with Uber and Airbnb, so bodies were taking their place alongside cars, apartments and offices—briefly dwelled in, tried out, passed along.

“How Whitney Wolfe Herd Turned a Vision of a Better Internet Into a Billion-Dollar Brand,” by Charlotte Alter/Austin for Time (March 2021). You have to assume that Bumble’s founder did not fully understand Alter/Austin’s opinion of her app, or she wouldn’t have allowed the journalist such generous access. This profile is full of subtly devastating — and openly sexist! — barbs: For all its high-minded claims, Alter/Austin suggests, Bumble is essentially just Tinder with a savvier marketing team behind it.

“Tinder Hearted,” by Allison P. Davis for The Cut (August 2022). This funny, whip-smart and occasionally brutal essay, which Davis has described as “a Livejournal entry masquerading as a feature,” was a finalist for a National Magazine Award in 2023. For me, it was also the piece that cemented a theory I’d been nursing since I started this project — that perhaps, for some people, online dating is less a means to a conventional end than a new approach to organizing one’s life and relationships. As Davis writes, the longest relationship she finds through Tinder is with the app itself: It empowers her to live a full life as a single person, without the stress or distraction of constantly looking for companionship.

“Age, Sex, Location,” by Kira Homsher for Longreads (March 2023). Welp, okay, didn’t mean to end on a down note — but I savored this lovely, lonely piece on the alienation of meeting and discarding online strangers, whether on Tinder or Omegle:

“I’d convinced myself that, in my frantic cycling through new people, I was wielding my youth to its fullest potential, perpetually carving myself anew. In opening myself up to so many people — and in exercising the self-restraint to close myself off again — I would become larger than myself, someone who could weather the capriciousness of the world and reflect it back unscathed … Every single person I connected with was a treasure to me, a lesson, something to tuck away inside a chest for safekeeping. Not anymore. The chest is full, and it rarely begs opening these days. I’ve been cured of my curiosity through sheer saturation.”

That's it! Until the weekend. Warmest virtual regards,

Caitlin

1. Although, as Alana Massey argued in 2016, maybe meet-sleazys ARE meet-cutes now.

2. This, from 2003, is in fact the best description of ghosting I’ve ever read: “Because online relationships begin in a state of mutual absence, ''disappearance'' may be the wrong word for a sudden lack of contact between two people who meet this way; more, these are failures to reappear from the digital murk that came first.”

3. This, for instance, is Alexander’s memorable description of an early-aughts singles chat: “a bizarre den of possibility where you could engage in hilarious/confusing/alarming conversations with boys pretending to be men, men pretending to be women, and men and women pretending to be attractive.”