Is This The End Of Digital Dating?

On the eighth floor of an office building in Chelsea, Robyn Swider explained to a group of three men that she was not, in fact, a yenta.

“Yentas are meddling,” she said cooly, glass of white wine in hand. The 26-year-old matchmaker, looking quite pretty in a pink J.Crew dress, certainly didn’t look like the famous Fiddler on the Roof character they had in mind.

For $5,000 Swider matches clients for Three Day Rule, a Los Angeles-based dating service that’s recently arrived in New York. You may have heard about the dating service’s website, which has received some criticism for using facial-recognition technology to match you with people who look like your exes. But, there is also a real-life person (in New York, that’s Swider) you can hire to go out into the world and meet people for you.

The company’s name is no mistake: It’s a play on the unwritten rule that you should wait three days before calling someone you like. TDR is throwing that idea out the window, bridging the physical and digital dating worlds with its online and in-person services.

In a world where online dating is essentially free, dropping $5K for the service is expensive. But, as Swider explained, for someone who’s constantly going out for cocktails and romantic meals, months of this can easily add up to that kind of money. And, then you end up at dinner with someone who you’re not totally connecting with. Swider vets potential matches that are worth your while — kind of like a personal shopper.

Talia Goldstein, founder of TDR, believes we’re caught in a kind of gray area where women are expected to take as much romantic initiative as men. “Guys aren’t traditional the way they used to be,” she explained. “Women have kind of taken control of their dating lives. They’re not just waiting around for a guy,” added Swider.

For the initial consultation — which comes free of both cost and pressure — Swider asked Christy*, a very cool client who agreed to let me sit in on their meeting, a lot of questions. She hit the basics, like age, height, job, and her version of “So, what brings you in today?” Then she moved on to the harder hits. Are your parents still married? Are you religious? What are your hobbies? What qualities do you most value in a match?

Apart from her admittedly terrible taste in television, Christy is a completely eligible bachelorette. She’s 27, beautiful, and quite funny. You could ask her about her job in the public health field, but she’d rather tell you about the time she spent in Africa building clean-water communities. She’s a catch. But, for those living in NYC, she’s one of a growing population of young women unable to meet someone in a city brimming with young hopefuls. Naturally Swider asked her, “Why are you single?”

Christy thinks people in the Big Apple have a very specific problem: “It’s like New Yorkers have Peter Pan syndrome,” she said, speaking to the ways we date a ton but don’t find many actual relationships. You know, not seeing someone past the fourth date or when those texts fizzle into radio silence. “Dating here can be kind of tricky,” she added. Christy’s tried Tinder, but found that, while she was open to dating, her matches were less so. OKCupid just stressed her out. She's met plenty of people through her job and social outings, but it’s still not working. “I date guys who are nice and smart, but there’s no spark.”

If you’ve done any kind of online dating, Swider’s questions probably feel familiar to you. But, the benefit of having a human asking these questions is that you get a chance to explain that which you cannot communicate by ticking boxes on a list. When Christy said her hobbies included adventurous activities, Swider responded, “So, you’re doer,” or “You’re more of an explorer, not a vacationer.” The TDR matchmaker functions as a liaison between the algorithms of online dating and how you articulate what you’re looking for. Swider is like a colored pencil, shading in the gaps between your own erratic coloring and the sharp, distinct boundaries of online-dating questions.

Her talents extend beyond translation, though. Sitting with her, you get the feeling she truly understands you. Christy told Swider she wants a man who is “kind, curious, smart (not necessarily book smart), and socially responsible.” She’s been drawn to finance guys in the past, but knows it’s been a history of poor matches. “What I want to be drawn to isn’t what I’m actually drawn to,” she said, noting she’s had a history of picking guys who are bad for her. In response, Swider pieced it together quite nicely: “You’re looking for someone who’s a guy’s guy on the surface, but underneath he’s got a little more going on.” I was tempted to slow clap.

Okay — but how was she going to find this guy? Just because Christy was interested in being set up doesn’t mean the male community would be interested in letting a stranger send them on dates — especially when TDR’s core demographic is people in their 20s and 30s. After all, if Christy’s having trouble meeting someone, what makes Swider any more qualified, or lucky, even?

So, Swider brought me to the networking event, at this nondescript Chelsea office building, to see her in action. Rather than set up gatherings herself, she’ll head to other organizations’ happy hours and business events after meeting with clients all day to source her match pool. And, these events are a great way to find gainfully employed, passionate, driven people. Plus, it’s an environment where strangers are expected to approach one another for conversation and exchange information. “You have to approach dating the same way you would a job: networking,” she said. I asked her what she looks for when she scans the room. There is some superficiality to it — she looks for men and women her clients have identified in part on physical traits. But, more importantly, her clients ask for someone who’s passionate, honest, “not rude to waiters,” and capable of teaching them something. “People don’t list ‘rich’ as much as I thought they would,” she confided.

I was impressed with the way Swider so easily approached people, not beating around the bush for one moment. Her greeting was direct: “Hi, I’m Swider. I’m actually a matchmaker. Are you single?” She’s smart to do this. “I never want to make a guy think I’m flirting with him. I need him to know what I’m here for.” When I asked her what made a good matchmaker, she didn’t say anything about knowing a lot of people. Instead, she claims you need to be brave, a good listener, and make people feel at ease. “You can’t be that elderly woman scaring girls about their biological clocks ticking.” That would be a yenta.

Still, I thought these guys would look uncomfortable when Swider dropped the M-bomb, or at least do that standoffish thing when they’re trying to look cool in front of other guys. Instead, they were quite interested. In fact, they couldn’t get enough. Even the ones who weren’t single wanted her card to pass on to friends.

It became clearest to me why New Yorkers are in need of TDR when I met Greg*, who happened to be at the networking event. Swider discovered him through a referral (Goldstein says about 80% of TDR clients are through referrals) and had set him up with some of her clients. He was in his early 30s, and it was easy to see why Swider had selected him for her client pool: friendly, smart, funny, attractive — who wouldn’t want to meet him? Even someone like Greg, though, has difficulty meeting women in the city. “I’ve always been no-games when it comes to girls I like. I’ll be very straight forward. But, that doesn’t really work.” There seems an unwritten rule that when you’re interested in someone, it’s better to pretend you’re not. Greg, who admirably abandons this silly tactic, still can’t meet a girl.

We milled around the party for an hour or so. Swider exchanged information with about eight men and women. Right now, TDR users are about 60% women, so she focused on getting some more men.

Though Swider and Co. give a new take on matchmaking, it will take time to ditch the lingering stigma of the business altogether (read: only desperate people need matchmakers). Though, Swider assures me, “No one has that desperate vibe.” And, I believe her — at least as far as New York is concerned. Her clients are a lot like you: upwardly mobile and carpe-ing diems left and right. It’s a great way to be, and arguably the only way to succeed in this city. That same lifestyle can leave you wanting in the love department.

Christy's going to start going on dates Swider arranged in the fall. Until then, she's hoping this is her last single summer in the city.