Inside the mind of a Philly matchmaker, whose business flourishes when ‘dating app fatigue’ sets in

Michal Naisteter approached a city planner at Reading Terminal Market and bantered with a pediatrician at the Bok Bar rooftop. At a Franklin Institute Science After Hours event, she was intrigued by a young entrepreneur, and she chatted up a Delaware politician at a local coffee shop.

No matter where she meets people, her introduction remains the same.

“Hey, I’m Michal. I’m a married matchmaker," she says. “Are you by any chance single, ’cause I think you’re really cute.”

All those people ended up saying yes to Naisteter, 35, who for two years has worked as a matchmaker for the national company Three Day Rule.

They are soon added to her company’s pool of more than 4,500 Philadelphia singles, most of whom are not paying members but are open to being set up. After a meeting where they have a “heart to heart" with Naisteter, she considers matching them with a client.

While many people may start humming along to the song from Fiddler on the Roof when they hear the word matchmaker, Naisteter’s company emphasizes a modern approach to what may seem like a quaint method for finding love.

There has been demand for matchmaking services as the proliferation of apps has chipped away at the stigma associated with seeking outside help for dating, an IBISWorld report on the growing $3 billion industry shows. Even with free options like Tinder at the fingertips of singles, some people turn to matchmakers for a more personalized, albeit pricey, experience.

People in Philly seem particularly disgruntled with the city’s dating pool, Naisteter said. Though loyal to the city, they say living here is like a small town where they already know everyone. That’s simply not true in the sixth largest city in the United States, she says.

For those who want to work with Naisteter, there is a $5,500 premium membership fee for three months, with higher priced options for six and 12 months. With this payment comes an in-depth meeting about anything from family history and past relationships to the attributes of a potential partner, as well as a professional photo shoot.

Then, Naisteter will search LinkedIn, Instagram, and networking events, or while living her daily life, like grocery shopping, to find people to match with her clients, with a goal of at least one match a month.

Other matchmakers range from national companies like the paid-service It’s Just Lunch to Danielle Selber, who is called the “in-house matchmaker” at the Philadelphia nonprofit Tribe 12, which encourages people to make a $36 donation if they are satisfied with the experience.

The way Naisteter views it, a matchmaker saves her clients time by searching on their behalf and then screening people before a first date to make sure they are representing themselves accurately and are a good fit. Her objective, she says, is getting people on fewer but better dates.

Three Day Rule launched in Philadelphia in May 2016, three years after its founding in Los Angeles. In that time, the company says, it has matched about 550 people in Philly and sat down with more than 1,500 singles. Naisteter has worked with more than 50 paying clients and of her current clients, the youngest is 26 and oldest is 67.

While Naisteter said there is not one metric for success, since not everyone is looking to be married right away if at all, the company said that in the last couple years, 70 percent of its clients overall were still dating one of their matches when their contract ended.

Even if the people Naisteter meets don’t fit well with a paying client, she helps them improve their dating profiles or offers general advice.

“I’m like a cheerleader and a sex therapist and your girlfriend all rolled up into one,” she said.

Three Day Rule CEO Talia Goldstein started listing her colleagues’ recent successes on one of their recent weekly conference calls with matchmakers in 10 cities, including Los Angeles and New York.

“For matching shoutouts, Melissa has two second dates and a third date. Samantha has a third date. Julia has a second date, and a client who went on hold to date her match...."

But when it was Naisteter’s turn, she didn’t highlight a traditional success like a wedding. She told a story about rejection.

He is in his 30s with a healthy career, but no relationship. Any time she sent him a match, he would ask: “What do I say to her?” “What do I text her?” “Where should we go?”

Naisteter has worked on empowering him to make his own decisions. “If you want to meet someone amazing, you have to be amazing yourself,” she would tell him.

So he gave it a try. He took a date to a ping pong bar in Philly and thought it was fantastic. But when Naisteter debriefed the woman after, she said he didn’t talk about things he did outside of work, and she didn’t feel as if he would be interested in what she does for fun, like salsa dancing. Naisteter relayed this to him and told him the woman wasn’t interested in a second date.

“So the next day, he wrote to me, ‘You know what, I think I’m still going to write to her, like I would be down to go as friends. I want to go salsa dancing, or I would come to one of the events that you organized,’” Naisteter told colleagues.

Naisteter considers her job more than just getting people dates. Along the way, she wants them to learn more about themselves and how that reflects what they are looking for in a partner.

In a way, she’d been readying herself to be a matchmaker long before she even knew a job like this existed.

After taking a human sexuality course as an undergrad at Pennsylvania State University, she went on to earn a master’s in that topic at Widener University.

She lived in Tel Aviv for a year, teaching English to children of migrant workers. She also worked in Boston and did HIV counseling on needle exchange vans. After working in public health, she decided she wanted to do more on the education side and learn Spanish.

So she went to South America with a backpack and suitcase and ended up in Medellin, Colombia, for four years. Back in Philly, she wanted a career change that blended her education, experience, personality and life history, and found this job while searching online with a friend one night.

While in Medellin, a friend set her up with her now-husband. The two have an 8-month-old daughter, Hanna Rodriguez.

With clients, Naisteter will tell them about her husband, Manuel Rodriguez. At 31, he is younger than her and from a different religion. “If we were on an app, I could’ve potentially swiped the wrong way.”

But instead of focusing on physical attributes or what was written down, the friend simply said: “You’re a good person, and he’s a good person."

They call that friend “our cupid, or our matchmaker.”

It isn’t likely that matchmaking services like Three Day Rule will overtake the online and mobile dating market, said John Madigan, an industry research analyst at IBIS.

Tinder, PlentyOfFish, and OkCupid are all brands from Match Group Inc., which IBISWorld reports has about 42.3 percent of the industry’s market share. Match Group’s stock has more than quadrupled to about $61 Monday from $15.20 in November 2015.

Dating sites like Match.com, eHarmony, and Chemistry.com comprise half of the market. Mobile dating, which can be found free with apps like Hinge and Bumble, is 31 percent. Matchmaking is just 12 percent. Match Group was an early investor in Three Day Rule in 2014.

But Madigan has noticed that “dating app fatigue” is driving demand for matchmakers.

“People are getting tired of swiping right, swiping left, ‘Do I find this person attractive?’ It’s a very superficial-based connection,” he said. While other matchmaking firms do this work, Madigan singled out Three Day Rule in his report because it has been “growing quite quickly,” doubling in revenue in 2018.

After spending years swiping through five different dating apps, Ed Cahan, 37, an engineer who works in real estate, was losing hope. His friends were married and having their second children, and he felt his time was ticking away.

He got coffee with Naisteter and asked how the premium membership worked.

“I thought about it for a couple days, and then I was like, ‘You know what, I tried all the apps, I tried all these things, Why not? I’ll say yes and I’ll see what happens.’”

So they met up again. Naisteter optimized his dating profile by helping him get new photos and linking his Instagram account to show off his woodworking hobby. She told him his usual date suggestion of coffee around 6 p.m. was just plain bad. Since he doesn’t drink, she suggested going to a nice restaurant at 8 p.m. for dessert and a better ambiance.

Cahan, who lives in Northern Liberties, told her how he was looking for someone who was Jewish like him, adventurous, entrepreneurial, and outdoorsy.

When she sent over his first match, he told her the next day that she nailed it. “You listened to me and you found exactly what I was looking for,” he recalled.

The two went on a dessert date last month at Parc. Even though he said it was a good date, the two haven’t gone on a second.

Now he is waiting for more matches.