Playing with Matches

By: Hannah Orenstein

For my family, Audrey, Jack, and Julia Orenstein





— Chapter 1 —


I can count on one hand the number of people I’ve told about my family’s mortifying secret. There’s my boyfriend. My best friend. That girl I trusted in high school who leaked it to my whole class. And now, my new boss, Penelope Winslow, founder and CEO of Bliss. I had to tell her to get hired; it was the only way I knew I’d land the job for sure. Anywhere else, the secret makes me a leper; at Bliss, it won me the job. Penelope says it’ll make me a star.

I hadn’t planned on telling her at all. I just really, really needed a job, and I had a hunch that spilling the secret would work in my favor. Up until two months ago, I had expected that People.com, the site I interned for in college, would hire me as an editorial assistant. I had imagined a future blogging about the Kardashians or The Bachelor—not exactly my passion, but it would set me up for a life as a writer. But the week before graduation, my boss pulled me aside. She didn’t have the budget to hire me. I didn’t have a Plan B.

For the next two months, I barely slept—I refreshed Craigslist and NYU’s job board every fifteen minutes and sent out dozens of desperate applications. I wasn’t looking for just any gig. You don’t get a decent scholarship to study journalism at NYU and still take out a sickening number of loans like I did just to fold T-shirts at the Gap. I spotted Bliss, the matchmaking service, during a Craigslist dive one sweltering night in early July.

“Seeking MATCHMAKERS!” the listing exclaimed. “Let us arm you with a quiver full of Cupid’s arrows.”

ABOUT BLISS: We’re an elite matchmaking service that connects New York’s most eligible bachelors and bachelorettes. Our clients are tired of meeting the wrong types of people online; they’re ready to seek our expert knowledge of the dating world and access to our unparalleled roster of clients, which includes successful entrepreneurs, politicians, lawyers, and artists. Our matchmakers will do whatever it takes to find the right match. If a client is a theater aficionado, a matchmaker might visit the after-party for a Broadway show to get the leading actor’s number. If a client needs a brainy intellectual for sophisticated pillow talk, a matchmaker might drop by a MENSA meeting. We’re not your grandmother’s yenta. Our method is highly individualized, brazen, and bold . . . and it works! Since our launch three years ago, a handful of clients have already sent us wedding invitations.

Matchmakers should be intuitive, creative, and above all, passionate about the quest for love. This isn’t your typical desk job. Instead, you’ll work around the city, in our downtown office, at home, or out on the town. You’ll be dreaming up exciting dates by day, and finding Mr. or Ms. Right by night. (We would never set up a potential couple to meet over dinner and drinks. How dull!)

Skip the traditional, boring cover letter and send us a photo of yourself and a note explaining why our clients should entrust you with the responsibility of finding love.

I stopped cold when I read the description. It reminded me of my family’s most shameful secret. Here it goes: My parents didn’t meet at a bar, or in college, or through friends (all of which I’ve claimed). There’s no reason a man from the commuter suburbs of New Jersey would ever bump into a farm girl from three hours outside Yekaterinburg, Russia. Not by chance, not through fate, not in some rom-com meet-cute.

My parents met through a certain kind of matchmaker. Dad was lonely, so he chose Mom out of a catalog and paid six thousand dollars to bring her over from Russia back in 1991. The few English words she knew came from Beatles songs. He liked that she was twenty years old, blond, and had boobs too big for her skinny frame. She liked that he owned a car with a cassette player. They weren’t exactly soul mates. Mom had me at twenty-two and divorced Dad by thirty after she became a naturalized U.S. citizen and he found an even younger blonde with bigger boobs. So, that’s it—don’t judge me.

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. Zuckerberg’s friend was a Patrick Bateman–type who’d appreciate it.