What It Really Takes to Work as a Matchmaker

What It Really Takes

To Work as a Matchmaker

When I first got hired to work as a matchmaker for an elite dating service in New York, I assumed I’d have to transform myself into a version of Patti Stanger. Thinking about her blunt confidence, decisive nature, and occasionally brash tone made me nervous. After a year of dabbling in matchmaking as a hobby — I set up my college classmates and wrote about their blind dates for a column on my school’s student-run blog — I was about to put my skills as a matchmaker to the test in a professional setting. I was terrified. On my first day of training, I was just 21 years old; my most formative romantic experience to date was getting dumped at a grocery store. Did I really have what it took to make it as a matchmaker?

During a series of training sessions, my fears were mostly put to rest. I learned that matchmaking is more of an art than a science, and that every matchmaker approaches it differently. I learned that my boss’s academic background was in communications and her professional background was in the hospitality industry; she was intuitive, excellent at reading people, and had an ultra-soothing presence. Her style of matchmaking was based on understanding people’s energy. Another matchmaker focused on offering coaching services to his clients, to make them feel as confident as possible on their dates. Another was naturally very social and liked to find fascinating matches for her clients while out with friends. The message was clear: as long as I followed a few basic principles of what makes a strong match, I could put my own spin on the job. I just had to figure out what worked for me.

I began the job with a small handful of clients, with the goal of taking on more as my skills progressed. Here’s how it worked at my company: Clients paid $600 a month for two first dates with different matches. Matchmakers were always on-call to offer pre-date pep talks, outfit advice, and post-date analysis. Every time I was assigned a new client, I’d meet with them one-on-one to learn about their relationship history, what kind of relationship they’re looking for now, what their lifestyle looks like, who they’re attracted to, and so on. From there, it was up to me to find potential matches, screen them all to determine which one are a good fit, choose the winners, and arrange the dates. I found matches in our company’s massive database of eligible singles, plus I used up to eight different dating apps and sites at a time, scoured my personal network, attended singles events, chatted up attractive people on the subway, and more.

I won’t lie, matchmaking intimidated me. I’m an introvert, not a people person. I had zero experience tracking down the kind of successful, sophisticated, attractive, and charming people my clients expected me to deliver. I was afraid people would lose faith in my abilities once they realized how young I was.

But I had one asset on my side. Prior to matchmaking, I had studied journalism, worked as a reporter for my school’s blog, and interned at a variety of magazines. I was a solid interviewer. And really, isn’t the process of getting to know my clients and their potential matches deeply just a series of interviews? The skills I used as a reporter — researching my subject, acting approachable, asking smart questions, and listening well — translated directly into my work as a matchmaker. It’s like what I learned in journalism school: You might not know everything there is to know about a topic when you begin reporting a story, but if you ask the right people the right questions, you’ll get there.

It was exhilarating to feel myself learning new things every day, whether that was a list of which hotel bars in Manhattan took reservations and which didn’t, or a profound lesson on love.

I loved matchmaking. It was my window into a new world. Sure, I might have been a 21-year-old who considered an eight-dollar bottle of wine to be a splurge, but my clients were glamorous, well-traveled 30- and 40-somethings with enviable careers. And I loved the adrenaline rush that came from toggling between dating apps, sprinting across the city to interview a match, and the sweet satisfaction of setting up a perfect first date. It was exhilarating to feel myself learning new things every day, whether that was a list of which hotel bars in Manhattan took reservations and which didn’t, or a profound lesson on love.

I also learned the importance of finding a career that suits your personality. As much as I adored my job, I crawled into bed every night feeling drained. Keeping up an aggressive social façade while carrying on dozens of intimate, deeply difficult conversations a day was not my cup of tea. I found myself missing the relative calm of my old life, typing alone behind a computer. Even when I wasn’t working, I didn’t feel like myself. I didn’t have the emotional energy to get through a date (for myself) after spending all day arranging dates for my clients.

Playing With Matches, By Hannah Orenstein

Ultimately, I scaled down my role at the company so I could return to college in the fall, and I left the position that winter so I could intern at a digital publication during my last semester of school. Once I graduated, I pursued work in media, as I had always planned — first, as a writer at Seventeen.com, next (drawing on my matchmaking experience), as the dating editor at Elite Daily. My first novel, Playing with Matches, came out earlier this year. It’s about a young matchmaker who’s in way over her head, drawing from my real-life experiences as exactly that. In the years since- I’ve set up a few couples on a purely recreational basis, but I have no interest in returning to my former career full-time.

I’m glad that I gave matchmaking a chance. It was a once-in-a-lifetime career opportunity and I’m so grateful that I tried something new. The experience truly changed my life. Even if I didn’t stay in matchmaking for long, it taught me a valuable lesson: an amazing job isn’t so amazing if it’s not suited to your personality.

My best match yet? Picking a career — writing and editing — that makes me feel like the best version of myself.

Hannah Orenstein

Hannah Orenstein is the dating editor at Elite Daily and the author of Playing with Matches (2018). Previously, she was the assistant features editor at Seventeen.com. At 21, she became the youngest matchmaker at a top dating service. She’s also written for the Washington Post, Cosmopolitan, Marie Claire, Refinery29, BuzzFeed, and Bustle. Her work has been featured in the Boston Globe, the New York Post, Us Weekly, USA Today, Hello Giggles, PopSugar, and Spire & Co.

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