The Dating Ring

Anyone who has tried online dating knows it typically goes one of two ways: 1. You get a match, you message, you flirt, it goes nowhere. 2. You get a match, you message, you flirt, you go out on a date — and maybe it goes somewhere. Brown University graduate Lauren Kay wants to change the game, cutting down on the aimless search process and pre-meet-up messaging for a more effective dating experience with her service, The Dating Ring. It might already sound familiar. The start-up first gathered a good amount of buzz earlier this year when Kay started a CrowdTilt campaign to fly single New York women to San Francisco, the theory being that there are approximately 50,000 more single straight females in Manhattan and vice versa in the Bay Area. Sounds like quite the party, no?

Kay’s CrowdTilt expired in mid-March, about $40,000 short of its intended goal, but the entrepreneur assured me that the trip will still happen. “We’re having a big party in San Francisco in late May. We haven’t announced yet who will be on the trip ... but people are pretty excited for it.” Sounds like a VH1 reality show waiting to happen? Sort of. “It was something that started out as a joke,” admitted Kay.

The next phase of The Dating Ring involves a matchmaker-type service that aims to work like Uber for online dating. When it comes to online dating shortcomings, Kay said she tapped into her friends’ frustrations with swipe-happy dating apps and catalog-like websites when developing the service.

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The Dating Ring not-so-subtly pointed (not swiped) a finger at one particular dating service during their Y Combinator Demo Day presentation. They compared driver-on-demand Uber to a Tinder-like service, where mindless yes/no swiping based on a photo and a handful of texts led to a more-likely-than-less wild card outcome — will you end up with the pristine Lexus SUV as pictured, or will your ride actually show up looking like a busted Chevy Astro? Who knows! And no, that’s not supposed to be part of the fun. Expectation setting based on a screening process is part of what supposedly makes Uber so successful (though this is debatable), so why, Kay wonders, shouldn’t an online dating service work the same way?

“I think what has happened is that online dating became so mainstream,” says Kay. “Back when online dating was new, it was a pretty select group of people who would use those sites and in a lot of ways it was more successful. When it became really mainstream it started taking too much time, sifting through profiles that were nothing like what they represented. It became an experience that people really disliked, it caused a lot of burnout, and it caused people to treat online dating like online shopping and just start writing people off. It is not romantic.”

A self-described “hopeless romantic,” Kay said it wasn’t that there was any shortage of singles in an area, but it was more of an issue with the way people were finding each other.

“I knew so many people who were having so much trouble dating in New York,” she said. “They were so smart and so dateable, attractive, and awesome, and really wanted to have relationships. Half of the people come up women and half were men, so it was not so much a problem women were looking for relationships and men were not, everyone was but really had no idea how to find anyone.”

So, she decided to create a dating service that organizes meet-ups with like-minded singles, on demand. Members are typically screened via intimate mixers facilitated by The Dating Ring’s matchmakers, where the team analyzes potential daters likes and dislikes, but also the way they interact with others in a small group setting. Then, their matchmakers coordinate group dates with their approved members that they think will spark. Unlike most sites, initial meet-ups are done in-person, no profile scanning allowed. But how do the pairings work?

“That’s the secret sauce,” said Kay. “We consider a number of things from age, to education, personality, and a number of things that we gather in that pre-screen. In general, what it comes down to is there are a few things that really matter in terms of background, age, and core values. There are also a whole lot of things that do not matter that online dating sites use to create these vivid, complex algorithms — but in general, the biggest piece of that is people need to meet in person and see if they like one another. Meeting is a very big part of attraction, but part of the problem is figuring out where people meet.”

The dates are $20 a pop and boast that an alleged 70 percent of their members go out a second time. The site is currently only available in San Francisco and New York, but Kay says Boston and Los Angeles are the next two markets they plan to launch. “The more signups we get over the next two months is how we will decide what city to launch in next,” she noted.

Group dating service Grouper and modern day matchmakers Tawkify have already taken stake in the Boston area, so we’re curious to see what The Dating Ring will bring to the table. A monetary investment and third party handling seem to be common factors (and possible turn-offs) in these options, but they all aim to cut down or eliminate the pre-date chit-chat and catalog pursuing time that typically comes with online dating. Does this mean in the new age of Internet dating, we’ll be spending more time off-line than on? Kay seems to think so.

“What we find is it is much better to set up four, five, ten dates a month, in person meeting people, then it is to spend hours online,” she said. “That alone is going to be a big difference.”