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Gershowitz slowly steers the conversation from the stats and the deal breakers and onto Leila’s preferences (“Social guys? When Leila starts to talk about her past relationships, Gershowitz adopts the tone of a therapist.“So you felt he wasn’t making space for a relationship? “I’m wondering if you feel like you can’t relate to those kind of men because you’ve had chapters in your life, and they’re still waiting for that first marriage,” she says at another.

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The crowd gathered around the Gansevoort Park Hotel’s swanky rooftop bar has been invited to “Join Manhattan’s most beautiful young professionals for a one evening only art and jazz event,” but it’s clear that most attendees care more about the beautiful young professionals than the art or jazz.

As they jockey for drink-ordering position, a few narrowly avoid stepping on the three-piece band.

Matchmaking may seem like an odd profession for a millennial, but Three Day Rule has six locations and 19 matchmakers like Gershowitz.

At a time when it has never been easier to meet significant others (or insignificant others) through an app or website, the company is raising money for plans to open 40 offices that offer old-fashioned matchmaking services.

When launched in 1995, it seemed like the matchmaking business was about to have its Amazon moment.“I wondered if we’re going to go out of business,” says Amber Kelleher, a matchmaker who had been working with the enormous database of singles her mother had started building, by hand, in 1986.

Now that anyone could access lists of potential partners online, she wondered if anyone would pay to access hers.Now, she says, she has many clients as young as 28.“As online dating is becoming normalized,” she says, “it’s driving up these niche apps and, at the same time, matchmaking.”“You’re 42?But instead of meeting the fate of local booksellers who battled their online equivalents, the Kellehers’ business grew.“It actually made it kind of cool to be proactive about your love life,” Kelleher says. They got to us faster.” Throughout the next several decades, her team expanded to 20 locations and 50 matchmakers.I agreed to not use her name, but let’s call her Leila.