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An elite matchmaker says executives’ biggest strength at work can make dating harder for them

November 15, 2026
in News
An elite matchmaker says executives’ biggest strength at work can make dating harder for them
Talia Goldstein, Founder of Three Day Rule Matchmaking, sits in chair smiling at camera,
Talia Goldstein, Founder of Three Day Rule Matchmaking, says that successful executives can struggle with dating. Cadie Thompson/ Business Insider
  • Having a high-paying job with power doesn’t necessarily translate to an easy love life.
  • The founder of Three Day Rule Matchmaking said execs can struggle with dating because it requires relinquishing control.
  • She coaches busy leaders to slow down, open up, and trust the dating process.

When it comes to finding love, successful executives often struggle with one thing they can’t control: chemistry.

In business, executives are used to getting what they want, they know what their end goal is, and they know what work needs to be done to achieve it, Talia Goldstein, founder of Three Day Rule Matchmaking, told Business Insider.

But this strength in their professional life doesn’t always translate to dating.

“Some of the executives struggle because you can’t control whether the person’s interested in you, you can’t control whether or not there’s chemistry, and that can be very frustrating for these top executive types,” Goldstein said.

Goldstein said that executives hire matchmakers to help them save time and energy, two things that their job often gets the best of.

But she said that her firm, which charges clients anywhere from $6,300 to roughly $100,000 depending on the membership, also provides its clients coaching to help them level up their dating game.

“A lot of what we teach them is to slow down and to get vulnerable and trust the process,” she said. “And that can be challenging for people who are so used to controlling their destiny.”

As part of this coaching, her firm also collects feedback from both parties after the date and uses that information to better understand how the client is perceived by matches.

Without feedback, people repeat the same patterns and are left wondering why they can’t land that second or third date, said Goldstein, whose firm’s clients are split roughly evenly between men and women.

“With matchmaking, we know exactly why. So it ends up making the process more enjoyable. And also you learn so much about yourself in this,” she said. “I think it’s the most valuable part of the service.”

Goldstein shared an example of a successful entrepreneur her firm worked with where every date he came back from the women would express liking him, but would then say the interaction felt more like one with a friend. Goldstein said the team was stumped as to why none of the women they were setting him up with were working out.

Thanks to the feedback sessions, they soon learned their client was ending each date with a handshake instead of a hug.

“That just felt like a business transaction and nobody was interested,” she said. “And that one small change made such a difference. But on your own, you would never have figured that out.”

Read the original article on Business Insider

The post An elite matchmaker says executives’ biggest strength at work can make dating harder for them appeared first on Business Insider.

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