The crowd gathered around the Gansevoort Park Hotel’s swanky rooftop bar has been invited to "Join Manhattan's most beautiful young professionals for a one evening only art and jazz event," but it’s clear that most attendees care more about the beautiful young professionals than the art or jazz. As they jockey for drink-ordering position, a few narrowly avoid stepping on the three-piece band. One literally backs into a painting as he starts a conversation with a pretty brunette.
Erika Gershowitz, a peppy 25-year-old with long brown hair that hangs over one shoulder, is doing the same thing as everyone else—scoping the crowd for attractive singles—but she’s doing it a bit more overtly.
"I have the weirdest question," she says as she taps the hand of a young Indian woman wearing a black leather moto jacket. "Are you single?"
The woman looks confused. Gershowitz, unfazed, flashes a lipstick-lined bright smile and holds out a business card. "I’m a matchmaker."
It’s a spiel she’s given innumerable times since she started her job with a company called Three Day Rule in May of last year. Matchmaking may seem like an odd profession for a millennial, but Three Day Rule has six locations and 19 matchmakers like Gershowitz. At a time when it has never been easier to meet significant others (or insignificant others) through an app or website, the company is raising money for plans to open 40 offices that offer old-fashioned matchmaking services.
Gershowitz does a lap around the room, her eyes darting to left hands as she scans for single status. She approaches a tall 35-year-old man who is leaning against a wall in classic single hovering fashion, cooly nursing what seems to be a fine whiskey. He says he is looking for someone "younger than me." Later, she talks with a preppy 45-year-old in a polo shirt ("I’m looking for a good normal person with a good head on her shoulders"); a tall man in a suit ("My fiancée is in the bathroom") and a busty woman in a tight black dress (who answers the question of whether she’s single with a flat "I’m straight").
As Gershowitz leaves the roof to have dinner with her own fiancé, she checks the hotel's lobby for singles she might approach on behalf of her clients.
When Match.com launched in 1995, it seemed like the matchmaking business was about to have its Amazon moment.
"I wondered if we’re going to go out of business," says Amber Kelleher, a matchmaker who had been working with the enormous database of singles her mother had started building, by hand, in 1986. Now that anyone could access lists of potential partners online, she wondered if anyone would pay to access hers.
But instead of meeting the fate of local booksellers who battled their online equivalents, the Kellehers' business grew. "It actually made it kind of cool to be proactive about your love life," Kelleher says. "People were able to take a baby step. They got to us faster." Throughout the next several decades, her team expanded to 20 locations and 50 matchmakers.
Online dating, meanwhile, transitioned from something most Internet users considered to be a dangerous hobby for cheating spouses to a mainstream activity. According to a recent Pew study, almost half of the public knows someone who uses online dating or who has met a spouse or partner that way, and one in five adults between the ages of 25 and 34 has participated in online dating themselves.
As online dating has become socially acceptable and widespread, niche apps have paired couples according to everything from music taste to travel plans. Some, like the League, cater to certain demographics. Others, like Once and Coffee Meets Bagel, intentionally limit the "always on the prowl" effect by allowing users to access a limited number of profiles each day.
Though nobody keeps stats on the topic, matchmaking seems to have simultaneously grown into a niche within this shifting, technology-assisted dating landscape. A trade group called the Matchmakers Alliance, founded in 2012, has about 150 members, who must each be referred by an existing member. "I started my business when there weren’t many matchmaking business," says Maria Avgitidis, the founder of Agape Match in New York City and a cofounder of the Matchmakers Alliance. "Now when I Google them, I’m like, holy crap, there are hundreds of them." Avgitidis says her clientele has also changed. Seven years ago, when she founded Agape, they were mostly between the ages of 38 and 55. Now, she says, she has many clients as young as 28. "As online dating is becoming normalized," she says, "it’s driving up these niche apps and, at the same time, matchmaking."
Gershowitz’s manicured hands flit between her laptop keyboard and a perfectly poised perch on her crossed legs. A woman in a stylish blue skirt and expensive heeled boots—a potential match for one of Gershowitz’s clients—sits across from her. I agreed to not use her name, but let’s call her Leila. She’s the founder of her own company, gorgeous, and speaks with the calculated fluidity of someone accustomed to appearing on conference panels.
And yes, she’s 42. No, she doesn’t mind dating people who are divorced. She’s divorced.
Yes, she’s fully divorced.
Three Day Rule clients get face time with the matchmakers who learn their preferences. They get fashion consultants. They get professional photography for their dating profiles. But really, the biggest value of bringing on a hired gun for your dating life can be summed up pretty easily: "Dating is a numbers game," says Gershowitz. "We essentially go on bad dates for people."
This date, however, seems to be going well.
Gershowitz slowly steers the conversation from the stats and the deal breakers and onto Leila’s preferences ("Social guys?" "Funny guys?"). Sometimes she throws out suggestions for her to veto or accept—"I can’t see you with someone who is slapstick funny"—and sometimes she nods and smiles as Leila fills her in. When Leila starts to talk about her past relationships, Gershowitz adopts the tone of a therapist. "So you felt he wasn’t making space for a relationship?" she asks at one point. "I’m wondering if you feel like you can’t relate to those kind of men because you’ve had chapters in your life, and they’re still waiting for that first marriage," she says at another.
When the conversation began, someone passing through the fancy hotel lobby may have mistaken it for a job interview. By the time it ends, it looks more like a social heart-to-heart. Yes-or-no questions about dating specs have somehow evolved into a high-level discussion about life that at one point includes the phrase "We’re all hurtling toward death."
The woman brings up Nora Ephron, who was married three times and considered herself lucky in love. "I want to be in love 10 times in my life, even if it’s the same person over and over again" she says. "That’s why I do want to be married again. I want to know someone the way you know someone when you live with them over many years."
"Well, that’s intimacy," Gershowitz offers. "Right?"
Matchmaking is almost by definition inefficient. Setting people up effectively requires knowing them to some extent, and knowing people requires time.
Automate this process too much, and you’re subbing in an algorithm for the human pixie dust that lends matchmaker-made matches their credibility ("Most apps that are built are built by tech people who really don’t know anything about love," Kelleher says. "They don’t know about connecting. They don’t have the intuition. They’re just tech guys"). Don’t use any technology, and your price point serves only a luxury market. Kelleher, for instance, charges between $15,000 and $250,000 for its year-long memberships. Agape typically charges $15,000 for six months.
Some companies have tried to hit a balance between automation and human curation. A startup called Dating Ring uses an algorithm to surface matches that matchmakers then choose from individually, and instead of face-to-face meetings or phone calls, it uses an instant messaging platform to exchange feedback. Customers can pay $40 per month for two matches or $80 for four matches (the company also offers a more traditional premium service starting at $2,500 per month). As of April, it had about 5,000 active members.
Three Day Rule's rates start at $3,500 for three months. Though it doesn’t use algorithms to make matches, theoretically, it becomes more efficient every time it adds a new profile to its database. It works because a bad date for one person is a good date for someone else.
"I’m definitely not going to set her up with [Bill]," Gershowitz says as Leila exits the hotel lobby through a revolving door.
Bill (not his name) is the 44-year-old never-married lawyer Gershowtiz originally had in mind when she asked to meet with Leila. "I think she’s already lived too much for him," she reasons as she copies and pastes the notes from her Word document into the Three Day Rule database.
Maybe next week or next month, she’ll set Leila up with someone else. Maybe that pair hit it off. And maybe they’ll live some modern-day equivalent of happily ever after. But as far as meet-cutes go, hiring a $3,500 matchmaker will never score much better than fumbling through awkward online dates. Both systems feel, at their heart, a bit cowardly. With online dating, there is so much inventory that an unrequited "right swipe" rarely gets noticed. With matchmaking, someone else goes to bars to hit on people you might like, goes on your bad dates, and experiences the lion's share of rejections and let-downs before you even know about them. Both systems come down to effectively managing a database. It’s not like you both reached for the same carton of milk in the grocery store.
But in a Tinder-ized world, meeting people is not necessarily the problem that matchmakers are solving. "There are just so many options," Three Day Rule’s CEO, Talia Goldstein, says. "I think it’s part of the trouble. If you go on a date with someone who isn’t exactly perfect, [the tendency is to say], ‘It's okay, there are a million more people on these apps.’"
In profiling the rise of online dating, Vanity Fair recently characterized the result as a constant swiping match that amounts to something like Uber for sex. "You’re always sort of prowling," one charming twentysomething named Alex told the magazine. "You could talk to two or three girls at a bar and pick the best one, or you can swipe a couple hundred people a day—the sample size is so much larger. It’s setting up two or three Tinder dates a week and, chances are, sleeping with all of them, so you could rack up 100 girls you’ve slept with in a year."
Goldstein says focus is a huge problem for her clients. "The amount of dating apps and how overwhelming it is has really helped our business," she says. "Because people are over it."
Some of the best matches she’s made have been people who didn’t fit the laundry lists of criteria her clients give her—people who would be bypassed on an app. She once set up a woman who was looking for a corporate Jewish guy "not in entertainment" with a Catholic film producer. She set up another who was looking for a "Newport Beach type of guy" with a tattooed, long-haired rocker type. Both pairs ended up married.
Bill, Gershowitz’s client, says he wants to meet a woman who is 38, but Erika has also been setting him up with women, who, like Leila, are amazing but slightly older. "They might not have the haircut you like or the guy might not be 6’1," but that’s not really what compatibility is about," she says. "People are so quick to write people off because they’re not wearing the right suit in their photo."
The matchmaker of yesterday may have worked to broaden their client’s dating pools. But the matchmaker of the Tinder age, when it’s the choice and not the scarcity that has become an obstacle, serves almost the opposite purpose.
"How often, as a single woman, does someone actually ask you what you’re looking for?" Gershowitz asks before her next matchmaking meeting. "I think that people leave here feeling like they have a better idea of what they actually want."