I Was A Professional Matchmaker & It Was The Best Career Move I Ever Made

I can't remember a time I didn't want to write for magazines. In middle school, I scrawled editorial suggestions in glitter gel pen in the margins of J-14, and I cut up issues of Teen Vogue to make collages to hang on my bedroom walls. So, when I got to college, majored in journalism, and landed internships at Seventeen and Elle, I felt like my life was finally coming together the way I had always hoped. But during my junior year, I didn't get the coveted magazine internship I really wanted — so I took a risk and started a weird job instead. I wound up working as a matchmaker at a dating service, and it completely changed the course of my life.

I wasn't always so open to making that leap, though. While I had set up some college classmates on dates, I considered matchmaking more like a hobby than a career path. During the fall semester of my junior year, I interned at Elle, where I met the magazine's advice columnist E. Jean Carroll, who also happened to run a matchmaking service. After I completed a magazine project for her, I struck up a conversation and mentioned that I dabbled in matchmaking, too. She offered me a job on the spot — but I didn't say yes right away. I told her I had to finish up my junior year. But in the back of my mind, I assumed I'd never really take the gig.

During my spring semester, I studied abroad in Paris. While I loved practicing French, exploring museums, and personally taste-testing every type of cheese the city had to offer, I admit I spent too much energy applying to that prestigious magazine internship I really wanted. I sailed through the Skype interview and couldn't stop thinking about how incredible the internship would be. I refreshed my email constantly, waiting for the acceptance letter. One sunny afternoon, while admiring paintings at Centre Pompidou, the modern art museum, I had a fully fledged panic attack because I was sure the email should've arrived already. I left the building in tears. Soon after, I found out I didn't make the cut.

Hannah Orenstein

Rejection felt like a splash of cold water — shocking, but not as bad as I had expected. More than anything, I simply wanted a plan. So in March, I emailed E. Jean and asked if the matchmaking job was still available. Luckily for me, it was. In April, I completed my matchmaking training via Skype by waking up at 2 a.m., Paris time, to study the mysterious, magical techniques of determining compatibility and chemistry. When I returned to New York in May, I began working as a matchmaker.

There's truly no one typical day in the life of a matchmaker, but the common denominator is that every day is busy. It takes way more effort than you might expect to set up a single date.

Each of my clients paid $600 a month for two blind dates. It was my job to get to know each of my clients on a deeply personal level, scout out the most exciting, interesting matches possible, and plan delightfully creative, romantic, and memorable dates. I had anywhere between four and 14 clients at a time; I worked on commission, receiving $120 for each date I set up.

There's truly no one typical day in the life of a matchmaker, but the common denominator is that every day is busy. It takes way more effort than you might expect to set up a single date. Every time I was assigned a new client, I'd meet him or her for lunch or drinks. We'd do a deep dive into their relationship history, their dating dealbreakers, and what they truly wanted in a partner. Next, I scrolled through my company's database of thousands of eligible singles to see if anyone seemed like a good match. If so, I'd confer with my colleagues to get the scoop on what the person was really like. If not, it was time to turn to the eight dating apps I kept active on my phone. I swiped and chatted for literally hours a day, every day. Every time I found a potential candidate, I'd set up an interview to learn more about them. I also made an active effort to go out often and meet new people everywhere. Once, I even served as a wingwoman for an athletic client who wanted to meet someone who shared her Jewish faith. I brought her to a yoga class that doubled as a Jewish singles' mixer held at sunset on the rooftop of a Manhattan penthouse; after the workout, we mingled and flirted.

Hannah Orenstein

Every night I had a client on a date, I stayed glued to my phone in case he or she needed a last-minute pep talk. Those were always fun! It feels great to ramp up a person's confidence — I genuinely loved my clients and it felt like important work to help them find love. The hardest part of my job was always the morning after each date, when I called my client and their date to see how the night had gone. Matchmaking is incredibly tough, and I didn't always get it right; I struggled with the hard conversations when I had to break the bad news that the match didn't want to see my client again.

While I felt like an awkward, unqualified fraud on day one, I soon felt more poised and professional than ever before. I could feel myself growing up in a way I never did when I sat in a cubicle at a magazine's office.

At the time, I was just 21 years old and knew basically nothing about what a happy, healthy relationship looked like. The most significant moment in my love life at that point was getting dumped at a grocery store. I was terrified that if my clients knew how old I really was, they wouldn't trust me to find them love — and why should they? I mean, what did I really know? I didn't want to outright lie, but I cut my hair into a mature-looking bob and vaguely nodded along to their jokes about growing up in the '80s, as if I could relate. I also worked harder than I ever have in my entire life. And it paid off: While I felt like an awkward, unqualified fraud on day one, I soon felt more poised and professional than ever before. I could feel myself growing up in a way I never did when I sat in a cubicle at a magazine's office.

The summer flew by. Despite my initial hesitation about the job, I found that I didn't want to let it go. I scaled back my client list so I could keep working part-time during the fall semester of my senior year. Ultimately, though, I knew my heart was still in magazines. I said goodbye to the job over the winter holidays, so I could have time to intern at Cosmopolitan during my final semester of school the next spring.

Playing With Matches

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I'm so deeply grateful that I broadened my horizons by testing out a different career path. It truly changed my life in two enormous ways I never could've imagined in my wildest dreams. First, I wrote a novel about a young matchmaker working at a dating service in New York. It's called Playing with Matches and it was published last summer. I'm still pinching myself; this was the coolest bucket list item imaginable, and I can't believe my book is really out there in the world. And second, my brief jaunt into the world of the dating industry opened my eyes to how fascinating the search for love really is. It changed the direction of my writing for good — and now, I'm the senior dating editor here at Elite Daily.

I used to cling so tightly to my five-year plan. But five years have passed since I took that matchmaking job, and now I can safely say that taking a risk was the best career move I've ever made.