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What It Really Takes to Work as a Matchmaker

Career

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.

Culture

Why Whiskey Should No Longer Be Categorized As “A Man’s Drink”

I walk into a room full of men and I know exactly what they're thinking: "What does she know about whisky?"


I know this because many men have asked me that same question from the moment I started my career in spirits a decade ago.

In a male-dominated industry, I realized early on that I would always have to work harder than my male counterparts to prove my credibility, ability and knowledge in order to earn the trust of leadership stakeholders, coworkers, vendors and even consumers of our products. I am no stranger to hard work and appreciate that everyone needs to prove their worth when starting any career or role. What struck me however, was how the recognition and opportunities seemed to differ between genders. Women usually had to prove themselves before they were accepted and promoted ("do the work first and earn it"), whereas men often were more easily accepted and promoted on future potential. It seemed like their credibility was automatically and immediately assumed. Regardless of the challenges and adversity I faced, my focus was on proving my worth within the industry, and I know many other women were doing the same.

Thankfully, the industry has advanced in the last few years since those first uncomfortable meetings. The rooms I walk into are no longer filled with just men, and perceptions are starting to change significantly. There are more women than ever before making, educating, selling, marketing and conceptualizing whiskies and spirits of all kinds. Times are changing for the better and it's benefitting the industry overall, which is exciting to see.

For me, starting a career in the spirits business was a happy accident. Before spirits, I had worked in the hospitality industry and on the creative agency side. That background just happened to be what a spirits company was looking for at the time and thus began my journey in the industry. I was lucky that my gender did not play a deciding role in the hiring process, as I know that might not have been the case for everyone at that time.

Now, ten plus years later, I am fortunate to work for and lead one of the most renowned and prestigious Whisky brands in the world.. What was once an accident now feels like my destiny. The talent and skill that goes into the whisky-making process is what inspired me to come back and live and breathe those brands as if they were my own. It gave me a deep understanding and appreciation of an industry that although quite large, still has an incredible amount of handmade qualities and a specific and meticulous craft I have not seen in any other industry before. Of course, my journey has not been without challenges, but those obstacles have only continued to light my passion for the industry.

The good news is, we're on the right track. When you look at how many females hold roles in the spirits industry today compared to what it looked like 15 years ago, there has been a significant increase in both the number of women working and the types of roles women are hired for. From whisky makers and distillers to brand ambassadors and brand marketers, we're seeing more women in positions of influence and more spirits companies willing to stand up and provide a platform for women to make an impact. Many would likely be surprised to learn that one of our team's Whisky Makers is a woman. They might even be more surprised to learn that women, with a heightened sense of smell compared to our male counterparts, might actually be a better fit for the role! We're nowhere near equality, but the numbers are certainly improving.

It was recently reported by the Distilled Spirits Council that women today represent a large percentage of whisky drinkers and that has helped drive U.S. sales of distilled spirits to a record high in 2017. Today, women represent about 37% of the whisky drinkers in the United States, which is a large increase compared to the 1990s when a mere 15% of whisky drinkers were women. As for what's causing this change? I believe it's a mix of the acceptance of women to hold roles within the spirits industry partnered with thoughtful programs and initiatives to engage with female consumers.

While whisky was previously known for being a man's drink, reserved for after-dinner cigars behind closed doors, it is now out in the open and accessible for women to learn about and enjoy too.

What was once subculture is now becoming the norm and women are really breaking through and grabbing coveted roles in the spirits business. That said, it's up to the industry as a whole to continue to push it forward. When you work for a company that values diversity, you're afforded the opportunity to be who you are and let that benefit your business. Working under the model that the best brand initiatives come from passionate groups of people with diverse backgrounds, we are able to offer different points of view and challenge our full team to bring their best work forward, which in turn creates better experiences for our audience. We must continue to diversify the industry and break against the status quo if we really want to continue evolving.

While we've made great strides as an industry, there is still a lot of work to be done. To make a change and finally achieve gender equality in the workplace, both men and women need to stand behind the cause as we are better collectively as a balanced industry. We have proved that we have the ability to not only meet the bar, but to also raise it - now we just need everyone else to catch up.