Manual Playing With Matches

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  1. Playing with Matches: Global-Z Team Learns All About Data Matching
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  5. WORD Presents Hannah Orenstein for PLAYING WITH MATCHES

I was afraid my clients would lose trust in me if they learned the truth about my age. But on the other hand, my youth was a professional asset. I had grown up with social media and online dating, which put me at an advantage to older matchmakers.

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Orenstein says that she used her matchmaking experience only as a jumping-off point: "Some elements have roots in reality, like the nuts and bolts of what it's really like to work as a matchmaker, but everything is fictionalized. Even though, like Sasha, I also worked with clients to find their life partners when I was barely old enough to drink and feeling totally lost about what a satisfying relationship should look like I first applied to intern at Vogue when I was 15 years old — a very kind editor wrote me back to explain she could not hire a high school student who lived in suburban Massachusetts," Orenstein says.

After a year of running the column, I met E.

Playing with Matches: Global-Z Team Learns All About Data Matching

Jean Carroll while interning at Elle. She's the magazine's legendary advice columnist, and she also runs a matchmaking service. I really idolized [Carroll's] magazine work, so I emailed her a note that mentioned my matchmaking experience on campus. She wrote back in two minutes to ask if I would come work for her.

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I was scheduled to study abroad the following semester, so I went to Paris and applied for a prestigious magazine internship I was dying over. When I didn't get the internship, I took [Carroll] up on her offer. And as much as Playing With Matches is about that truly relatable early-twenties career confusion, it's also a rom-com, filled with tons of drama, missed connections, and first-dates-gone-wrong.

A lot of this, of course, stems from Sasha's work at Bliss, but it also comes from her own life and the life of her best friend, Caroline. She liked that he owned a car with a cassette player. Mom had me at twenty-two and divorced Dad by thirty after she became a naturalized U. Bliss sounded like the opposite of the way my parents met. Bringing two people together based on a hunch that they would click sounded romantic.

I wanted to be a part of it. I sat up in bed in the middle of the night to apply for the job right away. I fantasized about befriending successful, handsome, well-traveled people at Ivy League mixers, gallery openings, and charity galas and making them all fall in love. In those visions, I had a sleek blowout, a less obvious nose, and the toned legs of someone who actually goes to the gym.

I laughed at some story from the guy who handed Mark Zuckerberg his first beer at Harvard, then casually slipped him my business card: Sasha Goldberg, Matchmaker. The card was thick with sharp corners. At my interview four days later, Penelope instantly made me feel at ease. She looked like a modern Marilyn Monroe—platinum curls and a splash of red lipstick and curves poured into a navy dress, with colorful tattoos snaking out from under her sleeves.

I thought the interview was going well; she seemed genuinely interested in hearing about my journalism degree and my internship at People. I recited my usual answer. And a quick learner. She looked bored.


It was so goddamn hot in the brownstone. A dribble of sweat formed behind my knee and snaked its way down my calf.

I actually wanted to work here. She had to understand. My mom was a mail-order bride from Russia. My dad picked her out of a catalog. They were married for a decade, but they never loved each other. Help people fall in love? But it was just bizarre enough to actually work.


After Penelope picked up her hanging jaw, she hired me on the spot. The office is off the Bowery, around the corner from Whole Foods and Intermix—a stately brownstone with curved wrought-iron railings on either side of the stoop and a heavy brass door knocker. I heave it against the door and hear a flurry of heels clicking against wood inside. Penelope opens the door. I reach for a handshake, like I did last time, but she clasps my hand in a red-taloned grip and leans in to kiss my cheek. The brownstone is the type of place I would sell organs on the black market for.

A marble staircase rises from the foyer and the dark wood floors creak as we walk. Penelope leads me through the dining room—decorated with a massive, glittering chandelier and a deep-red Oriental carpet edged with fringe—and pushes open a door to the study.

An emerald green velvet couch rests along one wall and a packed bookcase stretches from floor to ceiling on another. Penelope slips off her white pumps, folds up her legs to sit birdlike on the couch, and points to a tray of Godiva chocolate truffles on the glass coffee table. Penelope hands me a pad of paper and a red pen, then sinks back into the couch, touching a long, pointed nail to her lips.

Not really. That power is transformative. When we went to parties together in college, whatever small talk I attempted with the basics and the bros fizzled. But they all instantly fell for Caroline, because she has this bright, fearless thing going for her. People widened their circles to let her in. In this job, though, I have no one to rely on but myself. That scares me.

How do you know who to match? This is all you need to know. She sits ramrod straight with her chin in the air. Simple, huh? I want to believe her, but it seems too easy.

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Sometimes, I wonder if my boyfriend, Jonathan, and I are in the same league. We met when I was a sophomore studying abroad in Paris. I was at a wine bar in the 16th Arrondissement with Caroline when this American guy knocked over my drink. He asked if he could buy me a new one to make up for it.

I learned that his name was Jonathan Colton, and he was a junior at Columbia studying abroad. I was surprised to learn he was an econ major. Even he looked a little bored telling me about the investment banking internship he had lined up for the summer. He invited me to join him at the jousting tournament, and that became our first date. But looks and status?

WORD Presents Hannah Orenstein for PLAYING WITH MATCHES

Dad chose Mom specifically for her looks, and I inherited some of them—her clear green eyes, her full lips, her hourglass figure. And not the nice part. The tab is on Bliss, of course. Pick somewhere sexy—hotel bars are great. You know the type. You want to treat them, you know? You know, make them feel comfortable.

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