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The New Generation of Millennial Matchmakers Wants to Help Your Tinder Game

A growing group of millennials is trying to make matchmaking cool again.

"Do not meet for coffee," Sasha Silberberg, the 24-year-old matchmaker at OKSasha, told me about my upcoming date. "That's what every motherfucker does. That's boring. Go on an adventure."

Silberberg, who wears glitter on her face to meetings and uses words like "rad" and "chill," is not what I pictured when I arranged to meet with a matchmaker. But if she seems more like a friend or wingwoman than a matchmaking yenta, that's because it's exactly what she intended.

Silberberg, like a growing group of "millennial matchmakers," is taking a new approach to setting people up. In an age where apps like Tinder and Grindr have seemingly taken over the dating market, Silberberg wants to bring dating back to person-to-person interactions arranged under the watchful eye of a matchmaker. So she, and many others, are carving out a new market of matchmaking services for millennials, by millennials, much of which supplements online dating rather than seeking to replace it.

"People sign up to date with me because I make dating fun, and I help people be themselves more," Silberberg told me. "If you're not acting from your most authentic self during the dating process, you're going to have a really hard time with what you're actually looking for."

Today's millennial matchmakers (many don't even call themselves matchmakers, but use "dating coach" or "wingwoman" instead) are more like objective friends. Some, like Laurie Davis of eFlirt, surf clients' online profiles to help them find preliminary online matches, while others, like Sofi Papamarko of Friend of a Friend Matchmaking, work exclusively offline, matching clients with her own acquaintances or other clients. Silberberg, who used to be a Lyft driver in San Francisco, sometimes set up the people she drove.

"They usually picture an auntie being a matchmaker, not their cool, slightly older friend." — Sofi Papamarko

"Millennials want guidance," said Christina Weber, matchmaker and founder of Underground Unattached, an intensive three-hour, no-phones-allowed, small group dating experience. "I think that we're not taught how to have relationships with people. That's something that's deeply lacking in our education curriculum. [Millennials] are a little bit confused with how they navigate the relationship while they focus on building their careers. They want close relationships but don't know how to do it."

Like old-school matchmakers, they consult their client databases and send you on dates, but the focus is less on marriage and money and more on finding someone you just really like hanging with first. Millennial matchmakers also use a combination of intuition and logistics, such as location and interests. Are you Tumblr famous and love "dank memes"? Watch Huang's World and play Neko Atsume obsessively? These younger matchmakers have a lover to complement you in all your quirkiness, while older matchmakers don't even know what Snapchat is.

Of course, to most millennials, hiring a matchmaker seems old-fashioned and unnecessary. We're used to taking matters into our own hands (and iPhones)—hiring cleaners with Handy, finding somewhere to sleep with Couchsurfing, renting cars with Car2Go. Matchmaking services can be costly (a year with Papamarko starts at $249 for men and $349 for women; Silberberg's packages of services start at $1,000) while apps like Bumble and Scruff are free.

But Silberberg and Weber stressed that navigating the dating world on your own can be overwhelming, and plenty of young people aren't even sure what they're looking for in a match.

"Millennials are educated and they've spent all this time perfecting how to think with their brains, but dating is tapping into your feelings and emotions," Davis told me. Davis, who says she has successfully matched more than 100 couples (including some who have married), said having a coach around can give millennials the tools and the data to find the person they're looking for, whether through dating apps or in real life.

One of OKSasha's dating events. Photo courtesy of Sasha Silberberg

Dates set up by matchmakers can also feel safer than ones arranged by, say, Tinder. You're less likely to be ghosted or homme fataled by a match brought to you by a matchmaker, because there is a higher standard for personality and accountability.

Lisa Marion, who found her current boyfriend through a millennial matchmaking service, told me the prospect of a matchmaker seemed strange at first. "It seemed old, stuffy, hella expensive, and scary," she said. But when she found out about Papamarko and Friend of a Friend Matchmaking, she started to see it more like being set up by a friend. "She was affordable for a young person like me and just seemed like a great person."

"I'm sure there are some open-minded, intuitive, brilliant older matchmakers. But those aren't the stories I'm hearing," said Papamarko, who is 35. "People seem to find my relatively young age refreshing. They usually picture an auntie being a matchmaker, not their cool, slightly older friend."

Adam Anklewicz and Melina Condren were both struggling to date when they hired Papamarko. Anklewicz had been bringing a wingman to bars to no success. Condren was disillusioned with the online messages she was receiving, half of which were "creepy and gross," and the other half of which "seemed like generic messages men send to every woman under 35 in the hopes of getting a response from anyone."

Anklewicz signed up in December 2013 and met Condren in June 2014, after several other dates set up by Papamarko. The couple has been together ever since.

"The entire process was fun and easy," Condren told me. Anklewicz said that he "trusted her because she and I knew each other, and I'm friends with some of her other matches. But it wasn't a big investment, and the payoff could have been—and was—huge."

Marion added that "because of the financial barrier to entry, I think a matchmaker like Sofi has more serious and high-quality people in her roster. She sorts through the chaff to find the wheat for you."

And although many have suggested that dating is dead among millennials, the matchmakers see things differently.

"If you see surveys on millennials, I think you see a great deal of hope for wanting a partnership," said Jasbina Ahluwalia, who runs the matchmaking service Intersections Match by Jasbina. Ahluwalia pointed out that millennials are the children of boomers, the generation with the highest divorce rate.

"I can see why they would be jaded," she told me. "But love is something the vast majority of people seek—to be connected, to feel like someone has your back when you go to the doctor and you fill out that emergency contact. I think that's a universal thing. I don't think millennials are exempt from that."

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