I was a matchmaker, but lousy at dating

WASHINGTON • "I'm sorry, I'm just a little nervous," my date told me while fiddling with his glass of scotch.

I blinked. He was older and more educated than I was and probably made three times as much money. After going on what felt like a thousand first dates, I didn't get nervous anymore - but if anyone should have been nervous, it should've been me.

"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.

I started my job shortly after a break-up and was single for the next 31/2 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.

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.

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 favourite happy hour spots in the neighbourhood.

I told him I was writing a book - a romcom 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. Sometimes, I'd meet my date and recognise 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 roller coaster - 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.

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? I had assumed that asking a ton of questions was the best way to learn about someone because that's what I had learnt in my matchmaking training. But I was wrong.

I wish I could say Jules' 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 night in autumn, 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.

WASHINGTON POST

• The writer is the dating editor at Elite Daily.

A version of this article appeared in the print edition of The Sunday Times on July 08, 2018, with the headline 'I was a matchmaker, but lousy at dating'. Print Edition | Subscribe