Playing with Matches: A Novel - Softcover

Hannah Orenstein is the author of Playing with Matches and Love at First Like, and is the senior dating editor at Elite Daily. Previously, she was a writer and editor at Seventeen.com. She lives in Brooklyn.

Playing with Matches — 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.

“I heard you’re single,” I’d say in that scenario. “Let me know if you’re interested in a match.”

Then I’d stalk off in a pair of Manolo Blahnik pumps I couldn’t afford now, and pick up a fat paycheck.

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.com. But then she threw me a question I didn’t know how to answer.

“Why should I hire you?” she asked.

I recited my usual answer.

“Well, I’m a very hard worker. And a quick learner. I’m motivated to succeed here. I’m fascinated by the company.”

“Mhm,” she said politely. 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. Up until that moment, I’d been optimistic that I’d get at least a second interview, if not the job. But now I wasn’t so sure, and that hurt. I actually wanted to work here. So before I had time to panic over the consequences, I dropped the Secret Russian Mail-Order Bride Bomb to convince Penelope that I had to be a Bliss matchmaker. She had to understand.

“The thing is, I’ll be a better matchmaker than anyone else you could possibly hire,” I announced, maybe a little too loudly. “Because I know exactly how the wrong match can implode. 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. And that’s what Bliss wants to do, right? Help people fall in love? I can’t think of a more noble thing to do, and I don’t see how anyone else could be as motivated as I am.”

My words were jumbled and breathless; I didn’t have much practice telling people about my family. But it was just bizarre enough to actually work. After Penelope picked up her hanging jaw, she hired me on the spot.



Three days later, I’m at Bliss’s office downtown for my first day of training. 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.

“Darling, come on in! I’m so glad you could stop by for training today.”

She turns and cocks her head for me to follow. The brownstone is the type of place I would sell organs on the black market for. It’s on loan from one of Bliss’s investors. 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. “Want one? They’re a gift from a happy client—he just got engaged.”

I take one. 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.

“Matchmaking is the most powerful job a person can have,” she muses. “Think about it, what do people really want in life besides love? Success? Maybe. Fame? Not really. Let’s say you go to a party and people ask what you do. They’ll all work as accountants or in insurance or something dull. The minute you say you’re a matchmaker, the room will stop and all eyes will be on you. They’ll want you to set them up, give them advice, teach them what they’re doing wrong. You’ll see. That power is transformative.”

I’ve never known that kind of power, but my best friend Caroline has. 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 didn’t know what to make of her at first, but they always wound up enchanted. She’d tell stories about that time she took nude yoga classes during her meditation retreat in Tulum, that time she slept with her barista and he made her latte art the morning after, that time she took a selfie with Kim Kardashian. People widened their circles to let her in. This wasn’t some contrived act; she was really just like that. Once she’d dazzled them with her absurd story du jour, she’d introduce me with a matter-of-fact, “This is my roommate, Sasha. She’s fabulous.” And then it wouldn’t matter quite so much that I was the quiet, awkward one, because Caroline was in, and we were a two-for-one deal.

In this job, though, I have no one to rely on but myself. That scares me.

“How does all this work? How do you know who to match?”

“Write this down, Sasha. This is all you need to know.”

She waits for me to click open the pen and hover it over the pad. I’m hanging on her words and she loves it. She sits ramrod straight with her chin in the air.

“Looks and status,” she says slowly, watching me write it down. “Looks and status. That’s it. If they’re equally as attractive and equally as successful, they don’t need to have anything in common. They’ll want to hop into bed together and they won’t argue about money—the rest doesn’t matter.”

“That’s it?”

She reaches for a truffle, pops it into her mouth, and grins. “That’s it. Simple, huh?”

Looks and status . . . are people really that superficial? I want to believe her, but it seems too easy.

“So, you’re saying personality doesn’t factor in at all?”

“I mean, sure, you could make an argument for that.” She grimaces. “Think of looks and status as the minimum requirements—otherwise, your clients will be offended you even consider them to be in the same league.”

My parents certainly didn’t match up that way. But I guess they didn’t last. 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. He had sandy hair and deep blue eyes that were lit up by his navy blue sweater, so I wasn’t going to say no. I learned that his name was Jonathan Colton, and he was a junior at Columbia studying abroad. He was weirder than his preppy façade let on: he explained he was working on a research paper comparing Hogwarts’ architecture to that of real European castles; he also had plans to see a reenactment of a medieval jousting tournament that weekend. 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. I didn’t want to break away from our conversation even after our beers were drained. He invited me to join him at the jousting tournament, and that became our first date. That was more than two years ago, and we’ve been together ever since.

But looks and status? Don’t get me wrong, I’m pretty enough. Dad chose Mom specifically for her looks, and I inherited some of them—her clear green eyes, her full lips, her hourglass figure. But I also got Dad’s dark, curly-frizzy hair and a nose that’s a size and a half too big for my face. And when it comes to status, well, that’s a joke. Jonathan’s a WASP from Westchester, and an investment banker now. I’m a barely employed girl one paycheck away from moving back home to Passaic County, New Jersey. And not the nice part. I don’t know if I believe Penelope’s philosophy exactly, but I write her words down anyway and underline them twice.

“So, Sasha, the first thing you’ll do when you get assigned a new client is to invite them out for dinner or drinks. The tab is on Bliss, of course. Pick somewhere sexy—hotel bars are great. Not like the Marriott, obviously, but the Bowery Hotel, the Ace Hotel, the NoMad. You know the type.”

I do not know the type.

“It shouldn’t feel like a stuffy meeting. Your clients should never feel like you’re doing business, except for the business of finding love. Don’t just pick the first place off Yelp. You want to treat them, you know? That’s when you do the deep dive into what they’re looking for, their relationship history, who they’re attracted to, the works.”

“How do you get all that?”

“Start off slow, with an icebreaker. Maybe you comment on the weather or compliment something they’re wearing. You know, make them feel comfortable.”

I flash back to last week, when Penelope gushed over the basic black dress I always wear to interviews. Got it.

“But where do we find the matches?”

She pulls a gold MacBook off the table, opens it, and clicks around.

“Here. The first thing you do is go through our database. We had a developer out in Silicon Valley build this for us last year. It contains thousands of profiles of both clients and potential matches. You can filter by gender, sexuality, age, interests, deal-breakers, income, and height.”

Faces flash by, and it’s dizzying to think of how many people are in the database. I catch glimpses of their photos—a guy with a shiny bald head, a girl with loose auburn curls, a guy in a shirtless selfie taken on a sailboat, a girl looking serious in a charcoal suit. Penelope stops and scrolls quickly to the top, and their faces blur into one. She stops at the search bar and types in a name.

“I’m thinking Mindy Kaplan will be your first client. She just signed up, and I have a feeling you two will really hit it off. Similar backgrounds, you know?”

Ah. She means Jewish. Or at least Jew-ish. I haven’t been inside a temple since my Bat Mitzvah almost a decade ago. Penelope pulls up a headshot of a pretty brunette wearing bright pink lipstick.

“Mindy is thirty-five. She’s an executive at a TV network. She just wanted a husband and kids five years ago, you know? Really chic, smart, bubbly.”

I lean forward to examine her profile. The nu...