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Cupid's Cursor

We're still trying to convince ourselves that online dating is OK

Francois Guillot/AFP/Getty Images

It’s been ten years since The New York Times declared it socially acceptable to meet your mate on the Internet. “Online dating, once viewed as a refuge for the socially inept and as a faintly disrespectable way to meet other people, is rapidly becoming a fixture of single life,” wrote Amy Harmon in a 2003 piece charmingly titled “Online Dating Sheds Its Stigma as” According to a 2010 survey of recently married people, dating sites were the third most common way that these couples met. (The survey was commissioned by Today, one-third of America’s 90 million singles have used an online dating site. I’ve lost count of the number of times people have asked me, “Have you tried OkCupid?” as if it’s a home remedy to be applied to a pesky rash—never mind that I wasn’t even scratching.

But it seems we’re still trying to convince ourselves that technology-assisted matchmaking is kosher. Whether it’s yet another style-section trend piece or a shame-tinged confession that we’ve signed up for, we have yet to get collectively comfortable with the idea of looking for love online. Although 30 million have dabbled with online dating, that number is surprisingly low for something that ten years ago was supposed to be a “fixture” of singledom. What’s stopping the other 60 million singletons? Perhaps decades of Hollywood plotlines that have programmed us to look for love at the crowded party or the local dog park have dampened the thrill of finding a perfect match with a few keystrokes.

A new book by journalist Dan Slater, Love in the Time of Algorithms, explores the past and present of online dating: “the industry’s rise from ignominy to ubiquity.” Through a series of historical anecdotes and stories—including his own and those of his parents, who met in one of the first computer matchmaking experiments—he paints a broad picture of how the internet has changed the way we date and mate.1

The fundamental selling point of online dating is that no one wants to be alone, and even cold-hearted skeptics secretly want true love. “U.S. Census data from 2010 showed that 39 percent of all Americans believe marriage is becoming obsolete,” Slater writes. “Yet 47 percent of the unmarried adults who believe marriage is becoming obsolete say they would like to marry someday.” The point is tucked into a footnote, but more should probably have been made of it. Just because we are moving farther away from traditional norms in practice, does not mean we are moving farther away from them in our ideals.2 Online dating seems to exist in the chasm between.

Slater’s view is that online dating is not necessarily a way to meet better people, as many sites claim, but it’s definitely a way to meet more people who suit your tastes. “It doesn’t matter who you are or what you do. You can be a closet swinger, an out-of-closet deviant, or a U.S. congressman. You can be them all. … These portals not only present the whole human grid of desire and stimulation but make that grid real and attainable, nonvirtual, bounded only by the limitations of curiosity and imagination,” Slater writes in his chapter about the proliferation of niche dating sites. In the immortal words of T.I., you can have whatever you like.

But even online, the pool is deeper for some singles than for others, and this is where Slater, despite his proselytizing, reveals some of the profound limitations of online dating. Online dating lays bare the sexual economy in which some people (namely tall, white, wealthy men) are guaranteed winners, and others (black women, older women, short men, fat people of all genders) have a tougher time. While it’s true that these dynamics exist offline, too, online dating makes it easy to eliminate whole categories of people by checking a few boxes. Slater quotes a number of stats from OkTrends, the short-lived blog about OkCupid directed by one of the site’s cofounders, Christian Rudder. I underlined this one several times: “A woman’s desirability, measured in messages received, peaks at age twenty-one. At age forty-eight, men are nearly twice as sought after as women.”

As The Atlantic’s Alexis Madrigal wrote in an excellent response to an excerpt from Slater’s book (published in that same magazine), “It should also be noted: There isn't a single woman's perspective in this story. Or a gay person's. Or someone who was into polyamory before online dating. …. Instead we get eight men from the [online dating] industry.” Like most promises of the digital era, online dating hasn’t exploded all of the old norms so much as reinforced many and twisted the rest. Perhaps the paradoxical exclusivity of online dating is at the heart of why we’re still so ambivalent about collectively embracing it. In theory, online dating opens infinite doors; in practice, it works by limiting potential mates with the type of discriminating filters most of us would be far too bashful or polite to apply in real life.

For those of us who aren’t in the prom king and queen demographic, a new book-length case study offers some cheeky advice on how to identify and target your dating audience. Amy Webb’s memoir, Data: A Love Story, does not start from the premise that online dating offers all the answers; rather, it is a system to be gamed. Webb explains how she created a complicated process to find a man who met all of her criteria and then went about reinventing herself to appeal to that man. First, she made a matrix of the traits she demanded in a mate, and also the dealbreakers. Then she set up a series of JDate profiles for fictitious men who met these criteria. And then she observed what types of women messaged those fake men. This way, she could systematically size up her competition.

“My goal in this experiment wasn’t just to observe other women on JDate,” Webb writes. “It was to understand them deeply enough so I could model their behavior. I didn’t want to try to hide who I was or pretend to be someone else—I just needed to learn from the masters and present the best possible version of myself online. I’d use these profiles to collect data and learn from the women with whom I would soon interact. Then I could build a super profile—a sort of amalgam of the popular girls and my own data.” Her self-presentation is not quite as creepy as it sounds, though the takeaway is still disappointing for those of us who are averse to putting a PR-style gloss on our personality: To get what she wants, even the most charming, educated, successful woman must massage her assets to be appealing within the peculiar ecosystem of dating sites.

And so what follows is a makeover montage from a rom-com: Webb working out. Webb shopping for some better first-date outfits. Webb retooling her profile to be vaguer and friendlier. Webb changing her user name to incorporate the word “girl.”3 Webb selecting a cleavage-revealing profile pic. This is considerably more effort than some of the people profiled in Slater’s book are presumably putting in. And it’s further complicated by the propensity of online daters to lie about their age or profession or marital status. “Bad data in equals bad data out,” Webb writes. “Algorithms that dating sites have spent millions of dollars to refine aren’t necessarily bad. They’re just not as good as we want them to be, because they’re computing our half-truths and aspirational wishes.” Webb doesn’t make any value judgments about this fact of online-dating life, but it seems hard to deny that the amount of game-playing involved—and not just for singles who take it as far as she does—puts a damper on the experience for many.

But for Webb, at least, the gamesmanship works.4 In a payoff worthy of Nancy Meyers movie, Webb meets and marries the man of her dreams, a witty, sexy ophthalmologist who also loves to travel and wants two children. And she clearly feels not an ounce of shame about the lengths she went to in order to get what she wanted.

Both Slater and Webb show (directly or indirectly) the problem with dating sites: they reduce people to their photos—followed by some hard numbers about age, weight, and income—so it’s no wonder online dating mirrors offline sexual dynamics. Despite her borderline-crazy, data-driven contortions, Webb comes across as more realistic than Slater, with his laissez-faire approach to finding love online. The difference highlights the limitations of this modern mechanism for a timeless trouble. Slater may insist that online daters have nothing to be ashamed of, but it is Webb’s ability to work the system in such an extreme way—and celebrate it as an achievement—that presents the truly persuasive case.

Ann Friedman is a politics columnist for New York’s website. Find her writing, pie charts, and GIFs at www.annfriedman.comFollow @annfriedman.

  1. In the days of gender-segregated Ivy campuses, some Harvard nerds invented computer matchmaking as a way to meet girls. Slater's parents signed up.

  2. See this recent article “Married to the Plan” from The New York Times

  3. Webb explains that among the most popular women on JDate, “I often saw opening lines like, ‘I’m a fun-loving girl that enjoys…’ and ‘I’m a laid-back girl who wants…’ Starting this way was immediately disarming. If someone said to you ‘I’m uncomplicated, generally in a happy mood, and I like to do stuff,’ you’d want to hang out with him or her, even if it wasn’t romantic, right?”

  4. After massaging her own profile and making it public, she also creates a point system to evaluate the men who message her. Below a certain point threshold, she won’t even go out with them!