When the Boss of All Dating Apps Met the Pandemic

Tinder. Hinge. OkCupid. Match. A year ago, Shar Dubey became the CEO of a multibillion-dollar matchmaking empire. Then singles everywhere went into lockdown.
Shar Dubey
Photograph: Arturo Olmos

On March 1, 2020—11 days before the World Health Organization declared Covid-19 a global pandemic, and the scope of human intimacy shrank to the size of a touchscreen—Sharmistha Dubey became the chief executive of the largest internet dating company on the planet. Dubey had spent years climbing through the C-suites at Match Group, where the conference rooms are named after love songs and one of the walls is covered in wedding announcements. Now she had control of a $20 billion empire. Some of the most profitable brands in the business, including Tinder, OkCupid, Hinge, and Match, were hers to command, as were the love lives of tens of millions of people.

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Photograph: ARTURO OLMOS

The previous CEO, Mandy Ginsberg, had left Match Group to attend to health issues and to rebuild her house, which had been leveled by a tornado. Before she handed the tiller to Dubey, she sketched out a course for the coming months. There would be an international growth plan for OkCupid, which had just exploded in India; a push into the matrimonial market in Japan with an app called Pairs Engage; an investment in an Egyptian dating startup; and new paid features for Tinder, the company’s golden goose. “I’m confident we won’t miss a beat during this transition,” Ginsberg had assured shareholders. Match Group would be safe in Shar Dubey’s hands.

And then, to put things mildly, IRL courtship suddenly became about as appealing as kissing a used Kleenex. (Appropriately, the scientific term for used tissues and other infectious objects is fomite, which comes from the Latin word for “tinder.”) Dubey started getting calls: How does one date in a pandemic? Users wanted the answer, but so did shareholders. Match Group earns 97 percent of its revenue from subscriptions and other paid features. “If we’re expecting 10,000 new subscribers, and we see 6,000—and we see that for two, three, four days—you start to realize you have a pretty big problem,” Gary Swidler, Match Group’s CFO and COO, recalls. “And then the question turns to Shar: ‘What do you want to do?’”

Dubey, who is 50, has apple cheeks and sloped eyebrows that give her a fixed expression of sympathetic concern. Where Ginsberg was an effusive, emotive leader, readily sharing stories about her own romantic life, Dubey comes across as stoic in matters of love, even detached. “I’m a technologist,” she says. “I may not sound warm and fuzzy.” Yet her theories of partnership have shaped the past decade of online dating and earned her a reputation as a product genius. “She’s a little bit of an oracle,” Ginsberg says. If love is the product of choice and happenstance, Dubey has an instinct for how technology can amplify both.

Before she made any decisions about Match Group’s Covid-19 trajectory, Dubey asked for data on users’ behavior, particularly in Asia, where the virus hit first. The numbers showed something strange. In early March, activity had dipped across the company’s brands. But by the end of the month it had shot back up, way higher than before. On March 29, Tinder users swiped through more than 3 billion potential matches, a one-day record for the app. (The record has since been broken 130 times.) Across Match Group’s portfolio, daily messages went up by 27 percent. Young women were engaging more than they ever had before, by just about every metric (minutes spent, messages sent, matches made). First-time subscriptions had rebounded too, up 15 percent over the previous year. People weren’t patiently waiting for the world to reopen. They were dating like it was the end of the world.

“We didn’t know where this was going,” Dubey says. She had never run a multibillion-dollar company before. She had never lived through a pandemic. She had never even been on an online date. But her instincts had helped Match Group grow from a collection of desktop sites into a horizontally integrated marketplace for every conceivable type of lonely heart, from the Gen Z swiper to the boomer divorcé. And those instincts—what Dubey calls “subconscious patterns of data”—were telling her something that she wasn’t quite ready to share publicly: The coronavirus wouldn’t destroy online dating. It would reinvent it.

Photograph: Suzanne Saroff

Where Dubey grew up, in an Indian steel city called Jamshedpur, nearly everyone found partners through arranged marriage. Her parents met each other this way; so did aunts, uncles, cousins. Even as a girl, she says, she saw the purpose of courtship not as romance but as “capitalizing on the choices available to you.” Dubey’s relatives would look for suitors by working their own contacts rather than by hiring a professional matchmaker, but the general approach was the same. “It’s based on empirical data, wisdom passed on from person to person,” she says. Which values matter most? Where should couples be alike and different? Who belongs together?

When Dubey was 18, she was accepted to the prestigious Indian Institute of Technology. “My relatives were telling my parents, ‘Well, that’s it, nobody’s going to marry her anymore, because who wants a smart girl?’” she says. But her father, a professor of engineering, felt strongly that she should get her degree before marrying. He fended off talk of courtship until after she graduated, in 1993. She was the only woman metallurgical engineer in her year. (Sundar Pichai, the current chief executive of Google, was a classmate.)

Dubey had considered attending graduate school in the United States, but her parents couldn’t afford the application fees or the cost of the GRE exam. To save up, she took a job at a steel company, where she met a witty engineer named Partha. “I had a huge crush on him,” Dubey says. They didn’t get together until later, after they both enrolled in graduate school in the US—she in Ohio, he in Florida. A mutual friend reintroduced them, and they started talking by phone. The conversations went on for hours. Dubey realized it was more than just friendship when she had to use much of her monthly graduate stipend to pay the long-distance bill.

Dubey was in love, but the courtship went on in secret. Her family sent suitors her way, and she politely met with some of them to fulfill her part of the bargain. Partha, too, was expected to find a wife the traditional way. “He couldn’t tell his mom about me,” Dubey says. “In her world, love marriages happen in movies. They don’t happen in real life.” Finally, she and Partha broke the news to their families. Dubey’s parents didn’t meet her husband-to-be until two days before the wedding. The guest list was tiny. “Everybody was skeptical about whether this was going to last,” she says.

Dubey didn’t revisit the question of matchmaking until more than a decade later, in 2006. She and Partha had both taken jobs at i2 Technologies, a supply management company in Dallas, and had become parents to a baby girl. “I was quite happy,” she says. Then she got a call from Mandy Ginsberg, who had recently left her job running i2’s marketing department to join the online dating startup Chemistry. The new company, which was owned by Match, needed a director of product. Ginsberg asked Dubey to suggest some names. “I didn’t even try to recruit her,” Ginsberg says. “She called me back two days later and said, ‘I’ll do it.’”

The two women were friendly, and Ginsberg considered Dubey to be a “brilliant engineer.” She also loved the way Dubey spoke. “The accent is like listening to Charlotte Brontë,” she says. (Dubey’s Indian-inflected English has remnants of a grade-school education from British nuns, though Brontë is a stretch.) The day after Chemistry made its offer to hire Dubey, i2 sued Ginsberg for violating a poaching clause. The parties eventually settled. Dubey, for her part, had no idea what she was getting herself into. But she was drawn by the “instant gratification of building something” and the “anthropological aspect of the work.” She could be part technologist, part social scientist.

Photograph: Suzanne Saroff

In the early 1950s, a programmer in Manchester, England, taught a 4½-ton, 4,000-cubic-foot Ferranti Mark 1 computer to write love letters. Or he taught it to play Mad Libs, at any rate, because all the love letters followed a simple script: “YOU ARE MY [adjective] [noun]. MY [adjective] [noun] [adverb] [verbs] YOUR [adjective] [noun].” That early attempt to meld code and romance wasn’t much more than a fun ramble through the uncanny valley; as the programmer himself admitted, the Mark 1’s letters had “a very peculiar flavor.” But the project also pointed to a deeper lesson: When a computer puts the pieces together, they don’t always make sense as a whole.

By the following decade there were computerized “marriage bureaus” in England and Switzerland. And if you were an American college kid with $3 to burn, you could sign up for Operation Match. You filled out a 75-question survey about your personality and your ideal date, sent it off to be processed through an Avco 1790 computer, and got a list of compatible matches in the mail. The process was delightful, though not always useful. “Attraction is a very imperfect science,” David Crump, one of Operation Match’s founders, later reflected. Students didn’t always know what they wanted; one woman, after detailing her preferences, got matched with her roommate. “Of course, statistically, if you match up a million people, marriages are likely to happen,” Crump told Harvard Magazine.

By the time Dubey got the call from Ginsberg, statistics were on the internet dating industry’s side. Match, founded more than a decade earlier by an engineer named Gary Kremen, had normalized the idea of digitally sorting through millions of strangers to find your partner. (Some people had more success at this than others; Kremen’s own girlfriend left him for a man she met on the site.) In reality, though, Match couldn’t predict attraction any better than Operation Match had. The site was little more than a glorified directory. People could search for each other by age, location, religion, and even drinking habits, but they had to sift through all the pseudonymous profiles on their own. As the writer Jennifer Egan observed in 2003, online dating could seem like “a public bazaar for the sort of people who thrive on selling themselves.”

The purpose of the new spinoff site, Chemistry, was to compete with one of Match’s up-and-coming rivals. That company, eHarmony, had come out with a solution to the “public bazaar” problem: Using data from a proprietary 258-question personality test, its matchmaking algorithms would funnel down the torrent of search results into a dribble of potential soul mates. The company labeled itself a “relationship building” service, nothing like those “rapid and reckless” dating services. In television ads, eHarmony’s founder said his system was “responsible for more marriages per match than any online dating service.” Some caveats applied: The main site didn’t offer same-sex matches until 2019. Early on, eHarmony also rejected about one in six people for being poor marriage prospects, in some cases because they showed signs of depression.

Chemistry marketed itself as a big-tent matchmaking site, more inclusive than eHarmony. Part of Dubey’s job, as director of product, was to get Chemistry’s personality test up and running. It had been designed by Helen Fisher, a biological anthropologist at Rutgers University who believed that people’s personalities fell into four basic types—explorers, builders, directors, and negotiators—and that their partnership preferences could be predicted based on these types. “The first question on the test was to measure the length of your ring finger relative to your index finger, which tells you the amount of testosterone you were exposed to in the womb, which has a determining factor for some of your personality traits,” Dubey recalls. (Whether the ratio really means anything is still a subject of scientific dispute.) Another question: What do your doodles look like?

Doodles and digits were crude proxies for attraction or compatibility, as Fisher once conceded. A sociologist named Pepper Schwartz, who developed a questionnaire for one of Match’s competitors around the same time, told The Atlantic, “If I could concoct a test for chemistry, I’d make a zillion dollars.” Matchmaking, in its true form, was more art than science. But as a product, the personality quizzes were fantastic. “This hand question just gripped people,” Dubey says. “We’re all so vain.” Once users got onto the site, her team could observe them, as if in a virtual love lab.

When it became clear that the Chemistry experiment was working, the company asked Dubey to stabilize the business at Match. At the time, the site was still oriented around search. “We were called Match, but we didn’t do any matching,” she says. She mobilized a team to build a recommendation engine. It would email each subscriber a handful of curated matches each day, known as the Daily Five. They were based not only on stated preferences (you say height doesn’t matter to you) but also on observed behavior (a lot of the profiles you ogle belong to tall people). “There is sometimes a real dissonance between what you think you want and what you actually do want,” Dubey says. “You may not be able to tease it apart, but the system can.”

The Daily Five became Match’s signature feature. It drove an immediate uptick in “four-way conversations” (back-and-forth volleys of four messages or more), which the company considers a key predictor of whether matches will meet in person. But Dubey wasn’t satisfied. The site still felt too clinical, too much like vetting résumés on LinkedIn. And the chemistry gap—the distance between a promising onscreen match and a compatible real-life partner—was still too big. People looked different from their pictures, or they had nothing to talk about, or there simply wasn’t a spark. Dubey thought the experience of online dating should be more like mingling at a bar or a speed-dating event. It should create a space for kismet. “The only scalable way I knew how was live video,” she says.

In 2011 the idea seemed far-fetched. Average connection speeds in the US were about a twentieth as fast as they are now. Most Match users were still using desktop computers; fewer than a third of all Americans owned a smartphone. “The technology was terrible,” Dubey says. Nevertheless, Match started testing a live video feature. Every Tuesday evening, people could log on, get matched up, and play a series of one-on-one icebreaker games (charades, finishing each other’s sentences). If they liked, they could linger and chat. The site crashed often, and Dubey and her coworkers ended up scrapping the idea. But before they did, she picked up on one of those “subconscious patterns” in the data. “For the people who actually did manage to successfully connect, and who had enough bandwidth,” she says, “we found people talking for five hours.”

They were talking, in fact, much like she and Partha had in their early courtship. Dubey, who can be demure and even cagey about her marriage, didn’t use her own love story to vouch for the feature. But Ginsberg believes that it explains her dedication to solving this problem. “A lot of people in their lives don’t find true love,” she says, “and Shar was lucky enough to find it.”

Photograph: Suzanne Saroff

In the spring of 2013, Dubey left Match to run product at Tutor.com, which was owned by the same parent company, IAC. She liked the idea of applying some of the technology she’d worked on to a new kind of partnership: student and educator. By the time she returned to the dating side, in 2017, the industry had undergone a seismic shift. Two-thirds of all Americans now had smartphones. Baroque questionnaires and matching algorithms were old hat; the new fads were geolocation and gamification.

Tinder, spawned from an IAC incubator in 2012, was the standard-bearer for this new generation of internet dating services. While sites like Match and OkCupid had slowly made inroads with younger people on smartphones, Tinder launched directly on mobile and targeted the collegiate set. It shuffled people like a deck of cards. Rather than searching for someone specific, or waiting for an email with your Daily Five, you swiped through profiles with the flick of a thumb—left for no, right for yes.

The seeming beauty of Tinder was that it shielded people from certain messy emotions. “If I approach a stranger at a bar, I’m nervous about being rejected, and the other person feels hunted,” Sean Rad, one of the app’s millennial founders, told Forbes in 2014. “We get rid of all that.” If two people swiped right on each other, they could open a chat. If they didn’t, both sides were spared the awkwardness of a real rejection. Tinder’s algorithms had nothing to do with finding people their soul mates or even suggesting who they might like. Instead, the app used algorithms to rank users by hotness—or “desirability rating”—according to how often others swiped right on them.

Dubey was brought on as Tinder’s COO to “institutionalize” the brand within the Match Group. “I certainly felt like a mama goose over there,” she says. She wasn’t opposed to a playful company culture, including the occasional Nerf shootout. (“She was always on the outer edges,” a former art director at Match recalls, but she “wanted to watch everyone else have a really great time.”) At Tinder, though, the culture had been chaotic. Early on, Rad’s cofounder Justin Mateen started dating another cofounder, Whitney Wolfe, who was also the VP of marketing; the relationship ended badly, and in 2014 Wolfe had sued Tinder for sexual harrassment and gender discrimination. (They later settled.) Rad and Mateen were pushed out; Wolfe went on to start the dating app Bumble. Tinder became a preeminent example of bro culture and sexism in tech.

Every week, Dubey would fly from Dallas to Los Angeles, where Tinder is based. She had a habit of walking up to her younger employees’ desks, borrowing their phones, and swiping through matches while they looked on. As Dubey saw it, the app forced people to make hasty decisions. It offered too many choices and almost zero help sorting through them. And that put it in conflict with one of her core instincts, the same one that drove her to introduce the Daily Five at Match: “Sometimes,” she says, “we need to be told who we should like.”

Dubey suggested that Tinder introduce a Likes You feature, which would present subscribers with a smaller pool of people who’d already swiped right on them—in other words, surefire matches. Internally, she says, “there was a fair bit of resistance to doing anything that broke the paradigm.” The point of Tinder was to solve for rejection; this felt like stacking the deck. But Dubey pushed the idea through, and it launched in mid-2017 as part of a premium subscription called Tinder Gold. Within a week, Match Group’s market value increased by more than $100 million. The following year, Tinder subscriptions accounted for half of all revenue at the company.

After Dubey’s tour at Tinder, Match Group rewarded her with a promotion to president of the company, where she would work alongside Ginsberg, then the CEO. Although she left Tinder after only a year, her contributions there are “legendary,” according to Tom Jacques, the brand’s CTO. In product meetings, he says, “what will often come up in discussions is, well, what would Shar think about this?”

Earlier this year, Tinder’s engineers arranged for Dubey and me to match on the app. Her photo showed her with downcast eyes and a slight smile, her hair windswept. She’d left her bio blank, but her profile indicated that she and I shared some interests—wine, travel, art. She appeared as an ordinary middle-aged woman, the incognito queen on a tour among the commoners.

We spoke over Face to Face, a live video chat feature that Tinder had fast-tracked into the app in early July, when the waves of daily Covid cases and deaths were surging toward their summer peaks. Dubey materialized on the screen, in her dining room. She had been the Match Group’s chief executive for nearly a year and had spent most of it here, in yoga pants. “This year, my real life has become the dullest it’s ever been, but my screen life has become so much more interesting,” she said.

Match Group’s plans for video chat predated the pandemic, but the company had been in no rush to roll it out. A poll of Match users had found that, pre-Covid, only 6 percent of people were open to using the feature. By April, though, nearly 70 percent of users were open to it. (The home screen on Hinge cites a similar statistic, perhaps as a form of peer pressure.) “People’s avenues for meeting people had really closed,” Swidler says. “We became the only game in town.” Video chat helped turn what had looked like a bad hand into a royal flush. Match Group ended its pandemic year with 17 percent higher revenue than the year before.

Dubey was in many ways the ideal Face to Face match—well-lit, easy to talk to, not at all creepy. The experience was something like sitting at a cozy booth in a bar, except that we couldn’t see each other’s pores or whisper conspiratorially about the couple having a fight in the corner or bashfully stir our drinks during a lull in conversation. I could see the advantages of the format, even in non-pandemic times: There’s no pressure to go out for a full meal, or even a cocktail, and at the end of the night no one has to pick up the check. But when you meet a stranger in a space without context, what do you talk about? How can you tell if the vibe is off or if it’s just the Wi-Fi connection?

No one thinks that a tool like Face to Face will permanently replace the bar. But the pandemic opened a window onto a new kind of internet date, and through it Dubey sees the future. The Match Group companies have operated, until now, as marketplaces. People go there for a transaction—to find someone—then carry on with the relationship offline, or at least off-app. In principle, it’s not so different from hailing a ride on Uber or creating a grocery list on Instacart. What video chat did, Dubey argues, is persuade a generation of customers that there’s some value in sticking around. She predicts that, in the future, “our getting to know each other and flirting is going to be more online than offline.”

The experience is, for now, fairly flat. But eventually people might log on to Tinder for a few hours to sing karaoke or watch a concert, without the effort of swiping through two-dimensional cards. They will move fluidly back and forth between the physical and digital worlds. Elie Seidman, who led Tinder from 2017 to 2020, has described this as the next wave of online dating. Dubey believes some of it will unfold in virtual reality. The idea would sound blithely techno-utopian coming from any other technology CEO, but Dubey somehow makes it seem pragmatic. “My theory and instinct here is not very different from how I felt about video,” she says. “The line between virtual and IRL is starting to blur.”

Her instinct could be wrong. Maybe this future isn’t the one for you. Or maybe the only way to know for sure is to meet it.

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