#SWAAYthenarrative

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.

3 Min Read
Lifestyle

Tempted To Dial Your Ex: 5 Ways To Know Whether Or Not You Should Contact An Old Flame

Thinking of ringing up your ex during these uncertain times? Maybe you want an excuse to contact your ex, or maybe you genuinely feel the need to connect with someone on an emotional level. As a matchmaker and relationship expert, I was surprised at the start of the coronavirus quarantine when friends were telling me that they were contacting their exes! But as social distancing has grown to be more than a short-term situation, we must avoid seeking short-term solutions—and resist the urge to dial an ex.

It stands to reason that you would contact an ex for support. After all, who knows you and your fears better than an ex? This all translates into someone who you think can provide comfort and support. As a matchmaker, I already know that people can spark and ignite relationships virtually that can lead to offline love, but lonely singles didn't necessarily believe this or understand this initially, which drives them straight back to a familiar ex. You only need to tune into Love Is Blind to test this theory or look to Dina Lohan and her virtual boyfriend.

At the start of lockdown, singles were already feeling lonely. There were studies that said as much as 3 out of 4 people were lonely, and that was before lockdown. Singles were worried that dating someone was going to be off limits for a very long time. Now when you factor in a widespread pandemic and the psychological impact that hits when you have to be in isolation and can't see anyone but your takeout delivery person, we end up understanding this urge to contact an ex.

So, what should you do if you are tempted to ring up an old flame? How do you know if it's the wrong thing or the right thing to do in a time like this? Check out a few of my points before deciding on picking up that phone to text, much less call an ex.

Before You Dial The Ex...

First, you need to phone a friend! It's the person that got you through this breakup to begin with. Let them remind you of the good, the bad and the ugly before taking this first step and risk getting sucked back in.

What was the reason for your breakup? As I mentioned before, you could get sucked back in… but that might not be a bad thing. It depends; when you phoned that friend to remind you, did she remind you of good or bad things during the breakup? It's possible that you both just had to take jobs in different cities, and the breakup wasn't due to a problem in the relationship. Have these problems resolved if there were issues?

You want to come from a good place of reflection and not let bad habits make the choice for you.

Depending on the reason for the breakup, set your boundaries for how much contact beforehand. If there was abuse or toxic behaviors in the relationship, don't even go there. You can't afford to repeat this relationship again.

If you know you shouldn't be contacting this ex but feel lonely, set up a support system ahead of time. Set up activities or things to fall back on to resist the urge. Maybe you phone a different friend, join a virtual happy hour for singles, or binge watch Netflix. Anything else is acceptable, but don't phone that ex.

Write down your reasons for wanting to contact the ex. Ask yourself if this is worth the pain. Are you flea-bagging again, or is there a friendship to be had, which will provide you with genuine comfort? If it's the latter, it's okay to go there. If it's an excuse to go back together and make contact, don't.

Decide how far you are willing to take the relationship this time, without it being a rinse and repeat. If you broke up for reasons beyond your control, it's okay. If your ex was a serial cheater, phone a friend instead.

If there was abuse or toxic behaviors in the relationship, don't even go there. You can't afford to repeat this relationship again.

As life returns to a more normal state and you adjust to the new normal, we will slowly begin to notice more balance in our lives. You want to come from a good place of reflection and not let bad habits make the choice for you. Some do's and don'ts for this time would be:

  • Do: exercise ⁠— taking care of you is important during this time. It's self-care and maintaining a healthy lifestyle.
  • Do: shower, brush your teeth, and get out of your sweats.
  • Don't: be a couch potato.
  • Don't: drink or eat excessively during this time. Again, remember to maintain a healthy lifestyle.
  • Do: think positive thoughts everyday and write down the 3 things you are grateful for. Look at the impact of John Krasinksi's SGN. It's uplifting and when you feel good, you won't want to slide backwards.
  • Don't: contact a toxic ex. It's a backward move in a moment of uncertainty that could have a long term impact. Why continue flea bagging yourself?