“It’s just that, you know, you’re a matchmaker. Dates are kind of, like, your thing, right? You’ll have to tell me how I’m doing.”
Conversations like this one became routine once I started working as a matchmaker for an elite dating service in New York. You’d think I would take all the wisdom I gleaned from the job and apply it to my own life. I started my job shortly after a breakup and was single for the next three and a half years. My intimidating job title threw a wrench in my dates’ confidence. My so-called insider knowledge of the dating game made me overconfident, but didn’t do anything to boost my actual dating skills. It wasn’t a good combination.
My date that night had started out pleasantly enough — we both made the requisite murmurs of “Oh, cool,” when telling each other how we wound up in New York and our favorite happy hour spots in the neighborhood. I told him I was writing a book: a rom-com called “Playing With Matches,” inspired by my experiences working as a matchmaker. And that was it — game over.
He was suddenly too flustered to make eye contact. He checked in to “see how he was doing on the date” after our first round of drinks and again after our second. I had to repeatedly reassure him that he was fine. I wasn’t interested in seeing him again. His lack of confidence was a turn-off. So back I went to my pool of dating apps, lined up in neat rows on the home screen of my phone.
My experience as a matchmaker had taught me how to craft a profile as broadly appealing as possible to get the most matches; how to write opening messages that caught people’s attention; and how to juggle conversations on multiple apps at the same time. There was never a shortage of dates. I went out with a Ryan Gosling impersonator, a BBC anchor with the soothing voice, a film critic, a cowboy and an actual count. Sometimes, I’d meet my date and recognize instantly that we had no spark. Other times, the chemistry was giddy, electric, delicious. Thanks to my job, I always felt like I had the upper hand. I was smug and loved swooping in to save my date from an awkward silence with a well-timed question. Every date felt promising.
But they all ended up in the same disappointing manner: fizzling out after two weeks or two months. Most of the time, I didn’t mind. But a few of those fizzles stung, and the repetition felt like a rollercoaster — fun at first, but nauseating before long.
More than two years after I left my job as a matchmaker, I met my former boss, Jules, to catch up over sushi. She is the most perceptive person I’ve ever met. Halfway through our conversation, she said, “Can I give you a piece of advice?”
I was suddenly nervous. “Of course.”
“You like to control the conversation,” she said. “You ask a lot of questions. It makes sense, with your background as a matchmaker, but you don’t need to do that.”
Oh. My mind jumped to my never-ending string of dates. Was I ever letting these guys get a word in? If I wasn’t letting them take control of some of the natural lulls in the conversation, I wasn’t really getting an authentic understanding of their personalities. I had assumed that asking a ton of questions was the best way to learn about someone, because that’s what I had learned in my matchmaking training. But I was wrong.
I wish I could say Jules’s revelation changed the way I dated for good. For a while, I pressed my tongue to the roof of my mouth on dates when I was tempted to ask another question. And if a guy seemed particularly nervous, I shied away from mentioning my matchmaking experience. But those dates didn’t blossom into relationships, either.
Instead, one fall night, I found myself standing outside a bar with my head swimming. I was about to enter my third date of the week, and I needed to pull up the guy’s Hinge profile to remember exactly who I had agreed to go out with. Software engineer, Williamsburg, into dogs, I repeated to myself as I pushed open the bar door.
I wound up spilling my past as a matchmaker in under 60 seconds, once he mentioned that he actually worked for Hinge. There was an easy spark between us and I didn’t want to bite my tongue. I wanted to talk to him — so I did. The conversation bounced back and forth like a flawless game of tennis. I didn’t need to be anyone other than myself. And it worked.