Meeting with Samantha Kessler in the lobby of the W New York Downtown was like meeting with any other girlfriend — if that girlfriend's goal was to match you with the man of your dreams.
"I go in for the hug because it helps me tell how tall my clients are," she said as she released me from a familiar embrace.
Kessler works as a matchmaker for Three Day Rule, a modern matchmaking service that operates out of seven US cities, including New York. I met with Kessler, the matchmaker in residence at the hotel in leading up to Valentine's Day, to see if matchmaking would convince me to ditch dating apps for good — and maybe even help me find love in the process.
I sat down with Kessler and she pulled out her laptop. "This is going to feel half like filling out a dating profile, and half like a therapy session," she said.
She asked me for all the usual information — my age, where I live, my job, and my sexual orientation, as well as my religion, whether or not I want kids, whether or not I want to get married, how many siblings I have, and where I went to school.
She also asked me what I look for in a match, what my deal breakers are, whether or not my parents are still together, and why I think I'm single right now. Damn, this really was starting to feel like therapy.
My meeting with Kessler was an abridged, 30-minute introduction, but the matchmakers' usual initial sessions with clients last an hour.
And it's very extensive, too — from there, the love-seeker decides whether or not they want to become a paid client (most opt for the six-month package which, for $8,000, guarantees you at least six matches) or simply enter Three Day Rule's 60,000-person database.
I asked Robyn Swider, TDR's east coast regional manager, about the price tag for finding love.
"Our service is an investment, but it isn’t the $200,000 service that some matchmakers charge. We wanted something that was more accessible to a normal, successful person," she said. "Generally [our clients] are relatively successful. They’re working a lot, and that’s why they want to outsource their dating life."
But how is a matchmaking service really better than using a dating app?
"In every way," Kessler said emphatically. Given that the matchmakers have access to all the big dating sites themselves, they're not limited just to the people they've added to their database.
But more importantly, she added, "we’re meeting all of those people in person before introducing them to our clients — so we can meet 10, 15 people before introducing even one to our clients, so we’re really doing all the vetting."
That vetting process is very important, to both TDR and their clients. "Say I meet a [potential match] for my client, and they’re kind of socially awkward or a little weird or creepy —how do you define that online? It’s kind of just a gut feeling, and I think all of the matchmakers have really developed instincts for people, you can very much tell."
After six years in business, I asked Swider about the company's success rate. Success doesn't necessarily mean marriage, she pointed out, though there have been a number of those.
"Matchmaking isn’t necessarily pass/fail, so if we set somebody up and they date that person for two years and they don’t end up getting married, that’s still a success," she said.
"But there are also a lot of people who come to us and maybe don’t have a lot of experience dating — maybe they just got a divorce, and the dating environment now is entirely different for them — so our job is to get them confidence, get them that experience, get them out there."
Or, she continued, maybe they meet with a client who has a very narrow idea of what they want, someone who may not exist. "Then it’s my job to open up their mind and maybe test the waters, push the boundaries a little bit, and see if we can find someone that maybe they wouldn’t have chosen for themselves," she said. "That’s a success too."
This was not your grandmother's matchmaking service, that's for sure.
Growing up Jewish, my only reference point for a matchmaker was Yenta from "The Fiddler on the Roof." Well, that, and my Nana trying to set me up with Esther's grandson or Myrna's great-nephew or Hennie's neighbor's son. This, thankfully, was nothing like that.
"I think from a time element, this is absolutely worth it," Kessler said, "especially for busy professionals who are like, ‘I need to meet a person who I’d be willing to be in a relationship with; I don’t want to go to a bar and talk to a guy for 20 minutes and find out he has a girlfriend, or go on a dating app and have a weird dude say weird things to me. I want a quality match, someone who wants what I want.’ That’s what we’re doing."
A better quality, more personal process, resulting in better quality, more personal matches — that's what matchmaking services like TDR are aiming for.
But am I giving up dating apps for good? Not yet; I'm quite happy to join TDR's database of singles, but I'm not at the stage where I can afford to be a paid client. Throwing $6 a month at OKCupid is totally within my price range, however.
But it did feel more personal to me. By the end of our session, Kessler and I were laughing together like old friends. Professionally she goes by Samantha, she said, but I could call her Sam.
"I really become huge fans of everyone I meet," she said, "and I really fall in love with everyone — it’s a problem, because I become emotionally invested in wanting people to find love, and it happens. And when it does, it’s like the best feeling ever."