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Playing with Matches

A Novel

About The Book

Named a Best Book of Summer by Refinery29, Bustle, and PopSugar

“The best rom-com of the season…overflowing with charm and heart.” —Bustle
“The perfect Summer read—smart, funny, escapist, and bursting with charm.” —PopSugar

In the tradition of Good in Bed and The Assistants comes a funny and smart comedy about a young matchmaker balancing her messy personal life and the demands of her eccentric clients.

Sasha Goldberg has a lot going for her: a recent journalism degree from NYU, an apartment with her best friend Caroline, and a relationship that would be amazing if her finance-bro boyfriend Jonathan would ever look up from his BlackBerry. But when her dream career falls through, she uses her family’s darkest secret to land a job as a matchmaker for New York City’s elite at the dating service Bliss.

Despite her inexperience, Sasha throws herself into her new career, trolling for catches on Tinder, coaching her clients through rejection, and dishing out dating advice to people twice her age. She sets up a TV exec who wanted kids five years ago, a forty-year-old baseball-loving virgin, and a consultant with a rigorous five-page checklist for her ideal match.

Sasha hopes to find her clients The One, like she did. But when Jonathan betrays her, she spirals out of control—and right into the arms of a writer with a charming Southern drawl, who she had previously set up with one of her clients. He’s strictly off-limits, but with her relationship on the rocks, all bets are off.

Fresh, sweet, and laugh-out-loud funny, Playing with Matches is the addictive story about dating in today’s swipe-heavy society, and a young woman trying to find her own place in the world.


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, 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 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 numbers jump out first: she’s five foot two and makes $150,000 a year. I bet she lives in a doorman building with an elevator. She lists her interests as television, painting, astrology, weekends in Martha’s Vineyard, and fund-raising for causes like girls’ education and kids with cancer. Her deal-breakers are “not Jewish (sorry), not ready to settle down, poor hygiene, and bad manners.” And then, in the section about what she’s looking for: “I love my career and I’m great at it, but becoming a mother is the most important thing in my life. Family has always come first for me. I’d hope it would come first for my partner, too.” It could have come across as desperate, but she sounds sincere. I like her.

“Our database is extensive, but let’s say you don’t find Mindy’s perfect guy there right away. Then it’s up to you to search for single men.”

This is what I had imagined—trolling the city’s coolest parties for eligible bachelors and flirtatiously adding their numbers to my little black iPhone. One hundred percent terrifying. I’ve never dated that way. Before Jonathan, I just made out with the know-it-alls in my journalism seminars who seemed to have a lot of opinions about music and drugs and other things they read about in Vice. I had somehow survived four years in New York without ever dipping my toe in the New York dating scene for real.

“I go out and meet people, right?” I ask.

“Well, sort of. You definitely can do that. Georgie—one of the matchmakers you’ll meet later—specializes in that. She had one client who missed her ex’s sense of humor, so she went to stand-up comedy classes until she met the right guy for her. She had another client who wanted to meet a Hindu woman, so she went to a luncheon at a Hindu temple. And last Labor Day weekend, she spent three days hunting around Hyannis Port to track down a Kennedy.”

Holy shit. “Did she find one?”

“A Kennedy?”


She purses her lips. “I mean, technically, he was only a second cousin, but sure. Georgie cares about every client like they’re her best friend, you know? She gets so bogged down in finding them the perfect person.”

“Isn’t that the point of all this?” I’m starting to feel uneasy, like I’m not quite so sure what I signed up for.

“Of course, doll! But there are faster ways.” She reaches for her phone. The lock screen is a white background with the Bliss logo in bright Tiffany blue—two stylized capital Bs facing each other, like two pairs of lips. She unlocks it. “This is the real magic. Look—Tinder, Hinge, Bumble, The League, Raya, Coffee Meets Bagel, OkCupid, Her, BeLinked, JDate, JSwipe,, eHarmony . . . should I keep going?”

“You have profiles on all of them?” I ask, incredulous.

“All of them. And you will, too. That’s one of the reasons we hire matchmakers in their twenties. Young faces are the best bait on dating apps.”

“And the other reason?”

She laughs. “We try to hire girls who have actually had sex in the past decade. Our competitors are all women in their sixties.”

“Oh.” I don’t know what to say to that. I have, in fact, had sex in the past decade. As in, like, yesterday. “I almost wonder, though . . . wouldn’t it be easier to meet people in person?”

“I mean, I guess you could run around the city all day trying to meet men,” she concedes, tilting her head to the side like she’s unconvinced. “But that’s what our clients are doing, and clearly it’s not working for them, either. Dating sites and apps expedite the process. I was chatting with a dozen guys at once when you came in this morning.”

“A dozen?!”

“There’s Joey, the pro-tennis player with a fetish for older women,” Penelope begins, ticking him off on her finger. “That’s a definite no. We don’t want our ladies to feel objectified. Andrew, a lawyer. He seems promising. Maybe a little dull. Raphael might work out for somebody, but it seems like he only goes for real beauties. I’m still sussing out his type, but the size-zero models hanging off his arm in every photo aren’t a good sign. Hold on, I need to get to these,” she says, gesturing to her phone.

She bites her lip, thinks for a second, then taps out rapid-fire messages on an app I don’t recognize. I watch her grin and purse her lips, as if she’s actually flirting in real life. Between her pinup look for a casual Thursday at the office and her quick, dry appraisal of these randos, I feel as if I’ve briefly left planet Earth. Is this my life now? The brownstone is quiet, and suddenly I have visions of lounging for hours a day on this insane velvet couch, typing out messages to older men I don’t know. I can’t believe this is a real job. I run my hand over the velvet and feel the fibers prickle the wrong way.

She cackles loudly over a message. “Raphael claims to have slept with two Victoria’s Secret models. Not with that hairline he didn’t.” She tilts the screen toward me, and sure enough, the top of his head is covered with sparse wisps of dark hair. He’s twenty-seven.


“Don’t feel guilty, you can laugh,” Penelope says. “Most of them are assholes anyway.”

“Don’t we talk to any women?”

“Sure. Our clients are sixty/forty—more women than men—but straight women are harder to reach on online dating sites because all of our matchmakers are women. So the female matches we find tend to be through our own personal networks.”

“Can’t you make a profile as a man and look for women that way?”

“Technically, yes. But we don’t do fake profiles often. When you’re searching for matches, you’re searching as yourself. Your own name, your own face, your own bio. The more real it is, the more authentic it feels.”

She goes back to typing. I hear the front door open and a voice coo “Hello,” then the clacking of heels on the hardwood floor. A few seconds later, two girls appear in the living room. Penelope looks up from her phone and stands up, sauntering over to hug each one. They all exchange greetings. I stand awkwardly, waiting to be introduced.

“Ladies, this is Sasha, our new hire. This is Georgie and Elizabeth.”

Georgie is a tiny pixie of a thing in a men’s pinstriped white button-down—rumpled, like she had picked it up off a guy’s floor that morning—that falls mid-thigh, revealing just the flirty hem of black silk and lace tap shorts underneath, and a messy topknot. She gives me a brief once-over and a half grin—“Nice to meet you”—then turns back to her conversation with Penelope.

Elizabeth is Georgie’s polar opposite: she welcomes me with a firm handshake and a genuine smile. Her coral red sheath dress reminds me of something Anna Wintour would wear to terrify some underfed assistant. Unlike Georgie, she actually speaks to me.

“You’re going to have so much fun here,” she says with the instant ease of a person who knows how to make small talk.

I’m embarrassed to tell her I’ve never actually done this before, but I do anyway. I babble when I’m nervous. She doesn’t seem to care—not about the babbling, not about my lack of experience.

“Look, I dropped out of law school for this. I’ve never looked back.”


“Less money, sure,” she concedes. “But way more fun.”

She’s friendly right away, the way that drunk girls always are at parties, except I get the odd sense she’s actually like this all the time. Georgie gossips with Penelope in a low, throaty voice. Out of the corner of my eye, I see Georgie hold her hands eight or nine inches apart and hear a low giggle. Penelope’s eyebrows shoot up.

The training continues for the rest of the afternoon—we cover how to use the database, what to write to people on dating apps, how to grill each potential match to determine compatibility with clients. Georgie perches on the arm of the couch behind Penelope, and Elizabeth sits with her ankles crossed on the paisley loveseat across the room. They chime in with tips as Penelope talks. By the time I leave, my notepad is full of scribbles and my mind is racing. Penelope tells me she’ll be in touch soon to arrange my first meeting with Mindy.

“She’ll love you, darling,” Penelope calls to me as she leans out the doorframe over the stoop. “Nothing to worry about!”

Nothing to worry about. I can do this. Right? As I leave the brownstone and walk uptown to my apartment, it occurs to me that this whole matchmaking venture could be a total failure. This job requires schmoozing, and I’m not exactly a people person. But I have to make this work, or else it’s back to Mom and my stepdad Steve’s house in Jersey.

Reading Group Guide

This reading group guide for Playing with Matches includes an introduction, discussion questions, ideas for enhancing your book club, and a Q&A with author Hannah Orenstein. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.


Sasha Goldberg is a recent college graduate living in New York City with her best friend, Caroline, when she gets an unexpected job offer from Bliss, an elite dating service. Though her only experience with romance is having a successful relationship of her own with her college boyfriend, Jonathan, Sasha is determined to succeed for the people paying for her services, which include a bubbly TV executive, a forty-year-old virgin, and a consultant with a seven-page checklist for her perfect match. As she devotes hours to finding them potential partners, coaching them through tough moments, and hoping everything works out, she begins to realize the cracks in her own “happy ending,” and finds herself growing closer to a writer named Adam, who she’s recruited to date one of her clients.

A classic New York coming-of-age story, Playing with Matches is a funny, fresh, and honest take on dating and relationships in the internet age that asks the ever-important questions: How far would you go to find The One?

Topics & Questions for Discussion

1. Sasha’s secret about how her parents met is revealed in the first chapter, but it comes up again and again throughout the book. How does that origin story influence her views and decisions when it comes to relationships, if at all?

2. How do you think the technological developments in dating (apps, websites, etc.) have changed the process—for better and worse?

3. From the get-go, Sasha knows that she and Jonathan come from different worlds, but says she “feel[s] a thrill” when she thinks about his success and “normalcy,” especially when other people realize they’re together. How much do you think other people’s perceptions of our relationships dictate them?

4. When Sasha first meets Adam, she is setting him up with Mindy, but when it doesn’t work out, she goes out on a date with him instead. Do you think that crosses a line? What would you do in that situation?

5. How do you think men and women approach dating similarly and differently?

6. One of Sasha’s clients, Gretchen, is very specific about what she’s looking for in a partner. What would you expect or hope for when starting a new relationship? What would you be flexible about? Do you think that criteria or chemistry is more important?

7. Playing with Matches is primarily about Sasha’s romantic entanglements with Jonathan and Adam, but are there other kinds of love she experiences? How do those relationships influence her?

8. Sasha has a few key clients—Mindy, Eddie, and Gretchen—for whom she struggles to find matches. Who would you rather have the challenge of setting up?

9. Have you ever set up a friend? Have you ever been set up? Discuss the risks and the rewards.

10. Adam and Sasha have to keep their relationship a secret, as it violates Bliss’s rules on dating clients. Would you be able to conceal your relationship like Adam and Sasha? What are the pros and cons of hiding something like this?

11. Compare and contrast Caroline’s and Sasha’s approaches to dating and relationships. Do you think that one is better than the other?

12. When Sasha considers getting back together with Jonathan, Caroline voices her disapproval by listing the times he has let her down as a boyfriend. Do you think this is appropriate? Is her honesty necessary?

13. At the end of the book, Mindy surprises Sasha with news that she’s pregnant. Sasha’s response changes everything. How would you handle that situation? Do you think Sasha does the right thing?

14. The title Playing with Matches is multilayered, a twist on the expression “playing with fire” and the idea of “matching” with someone on a dating app. Having finished the book, what other subtle meanings or messages do you think emerge?

Enhance Your Book Club

1. Playing with Matches joins the ranks of great romantic coming-of-age stories like Something Borrowed, Good in Bed, and Eligible. Choose one of these books to read in your book club, and compare and contrast their depictions of dating, love, and growing up.

2. Create a menu for your book club meeting inspired by Sasha and Caroline’s favorite girls’ night foods from the novel. Or, if you’re in New York City, visit Hotel Tortuga, David’s Bagels, or Brooklyn Bazaar.

3. Playing with Matches has all the elements of a classic romantic comedy. Poll your book club and see which rom-com is the group’s favorite. Then, as you watch it together, mark down the similarities and differences between it and Playing with Matches.

A Conversation with Hannah Orenstein

You’re a dating editor at Elite Daily, and were once a young professional matchmaker yourself. What elements of those experiences helped you to write Playing with Matches?

I knew that I wanted to write a novel of some kind, but I wasn’t sure what it would be about. The minute I got hired as a matchmaker, I knew I had stumbled onto something really special. My job was a lot like Sasha’s: I spent my days scrolling through a massive database of New York’s singles, swiping through dating apps, and setting up dates.

If you’re a person who can afford to hire a matchmaker, you’re likely in your thirties or older. I was just twenty-one at the time, and so I was never interested in any of my clients or matches. But people kept asking me what would happen if I wanted to date one of them. That question became one of the central conflicts of Playing with Matches.

In my own experience, even if I had met someone like Adam, it wouldn’t have been an issue. I recall my boss saying, “If a hot, successful man lands on your desk and you don’t take him for yourself, there must be something wrong with him!”

What was the most rewarding part of being a matchmaker? The most stressful? Any fun stories you can share?

There’s no better feeling than a client telling you that she or he had an amazing date. Matchmakers really do have the power to change a person’s life. On the flip side, it was always crushing to tell a client that their date didn’t want to see them again.

One of my most entertaining experiences was working with a woman who loved fitness. I wound up taking her to a Fifth Avenue rooftop yoga class that doubled as a Jewish singles’ mixer. We didn’t want to tell anyone that I was her matchmaker, so I said I was her friend—and during the coconut-water cocktail hour after the class, I acted like her wingwoman.

Sasha expects that when she starts working at Bliss, she’ll be attending exclusive events and pounding the pavement to find potential clients and matches. Instead, she learns that a lot of the job is being on apps and recruiting people that way. How did you think to put that twist on the process?

I think most people would be surprised to learn two things about matchmakers: first, that there are so many of them; second, that a lot of them use dating apps! Every matchmaker works differently, and not all of them are on Tinder, but I certainly was. (And on Bumble, Hinge, Coffee Meets Bagel, JSwipe, etc.) I spent hours a day swiping, conversing with matches, and meeting men for coffee to screen them for my clients. Most guys assumed I was either a bot, trying to sell them a membership, or using matchmaker as a “cover” and really just on Tinder to score dates for myself.

There’s a long tradition of young female coming-of-age stories set in New York City, on-screen and in books. Were there any influences you drew on during your writing? How much did you want to draw on them, if at all?

Oh, absolutely! The Devil Wears Prada by Lauren Weisberger was certainly an influence. Her protagonist Andy Sachs inspired so many people to aspire to the magazine industry. It would be incredible if Sasha Goldberg could do the same thing for matchmaking. There were other books that I devoured and admired the same year I wrote Playing with Matches that probably had some influence—all either female coming-of-age stories, stories set in New York, or both: The Royal We by Heather Cocks and Jessica Morgan, Luckiest Girl Alive by Jessica Knoll, Normal Girl by Molly Jong-Fast. And on-screen, I loved how unapologetically millennial Girls, Broad City, and Trainwreck were. That was something I consciously wanted to incorporate into my own work.

You seem to have a lot in common with Sasha, but are there any other characters in the novel that you relate to?

I can empathize with every character in the book to a certain degree—even Jonathan. But I feel closest to Caroline. Like her, my first summer after graduation from NYU was tough. My friends were landing amazing jobs and were dating great people, whereas I was unemployed and single (and writing this book). I felt somewhat lost and lonely after graduation, and I hadn’t expected to feel that way. Caroline certainly goes through a similar experience.

There’s a tendency in pop culture to portray young women like they “have it all.” Sasha seems to on the surface, but is really just trying to figure it all out. What did you like about writing a female protagonist at this age and stage of her life? What was most challenging?

I wrote the first draft when I was twenty-two, and a lot of mundane details about Sasha’s life were pulled directly from my own: like her, I made friends with the owner of the wine store to get sale-rack bottles for even less money, I was really impressed by people who could afford (and have room for) dining tables, and I used a “No Scrubs” lyric in my Tinder bio.

And like Sasha, I ate pork nachos at Hotel Tortuga, ate breakfast at David’s Bagels, played Skee-Ball at East Village dive bars on dates, hung out at Think Coffee and the Strand, and shared an apartment on First Avenue and Eighteenth Street with my best friend from college. I wanted this book to feel like a love letter to all my favorite places in New York.

The challenging piece of that was to accurately portray someone struggling to pull her life together as a twenty-two-year-old recent college grad in New York . . . while I was trying to pull my life together as a twenty-two-year-old recent college grad in New York. During my first conversation with my agent, she was like, “Adam is so obnoxious because he’s this older guy stringing along this younger girl.” And I was thinking, “Oh, that’s obnoxious? I didn’t realize that!”

Social media in its many forms plays a huge role throughout Playing with Matches, and it feels completely natural, because it’s such a presence in our everyday lives. How do you think social media is changing our approach to telling—and writing—stories?

I’ve been writing fiction on and off since I was a kid. When I was in middle school, I tried to write a novel entirely through AIM messages. I can’t imagine writing something about people my age that doesn’t incorporate social media and the internet. If you’re publishing a book about dating in 2018, it would be weird if it didn’t heavily feature dating apps.

Mindy’s surprise news at the end of the novel is quite a twist. How did you think of it? Did you know the ending when you started writing the book?

I did. I had the whole book mapped out chapter by chapter before I started writing it. It was really important to me that Sasha ended up single. She’s young! She doesn’t need to settle down! In her next phase of life, I can imagine her focusing on her career as a writer and simply enjoying her early twenties in New York. I wanted at least one character to have a happily-ever-after, and I loved giving those to Mindy and Eddie. Mindy winds up in a place she didn’t necessarily expect, but I think that ultimately, she got what she wanted.

Now that you’ve written your first book, do you have any ideas or plans for others? What subjects, situations, or characters would you like to tackle next?

Yes! I’m always interested in women’s careers, relationships, and friendships, and how they all intertwine.

About The Author

Photograph by Sylvie Rosokoff

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

Product Details

  • Publisher: Atria Books (June 26, 2018)
  • Length: 320 pages
  • ISBN13: 9781501178481

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Raves and Reviews

“Struggling post college, Sasha takes a job as a matchmaker. So what if she lacks expertise? But when she falls for a client, she’s thrown into it’s complicated limbo. Hannah Orenstein’s debut is a hilarious look at dating – and swiping.”
Us Weekly

"Funny, sexy, and absurdly entertaining."

"Millennials looking for their perfect beach read this summer need look no further than this delicious romp through the madness of dating in your twenties."
—Jo Piazza, co-author of The Knockoff

"A smart, feel-good rom com . . . . Reading Playing With Matches will give you butterflies of your own."

"The perfect Summer read — smart, funny, escapist, and bursting with charm."

"The best rom-com of the season . . . . overflowing with charm and heart."

"Playing With Matches is a fun, drama-filled, behind-the-scenes look at the life and love of an elite New York matchmaker—from a former insider who’s lived to tell the burning tale."
—Camille Perri, author of The Assistants and When Katie Met Cassidy

“It only makes sense for apps like Tinder to be part of romantic comedies . . . . “Playing with Matches” can appeal to people who have yet to swipe right, too.”
—The Boston Globe

"This rom-com is sure to brighten your summer."

"Playing with Matches is the fun, fast-paced summer read you’ll devour regardless of your relationship status."
—Hello Giggles

"Delightful. A fun and relatable rom-com for the Tinder age. Get ready to swipe right!"
—Georgia Clark, author of The Regulars

“Hannah Orenstein is one of this generation’s most essential voices on love. Everything her characters go through will stay with you for your twenties and beyond.”
—Dana Schwartz, author of Choose Your Own Disaster

"If you grew up with Gossip Girl and you obsessed over Devil Wears Prada, this is the book for your life now! It’s smart, fun, sexy, and deeply relateable for every Badass Babe!"
—Ann Shoket, author of The Big Life and former editor-in-chief of Seventeen

“Sasha, a likable heroine with a quick wit and a self-destructive streak, will appeal to fans of Marian Keyes, Helen Fielding, and Sloane Crosley . . . . a realistic yet romantic portrait of modern dating.”

"Love in the age of Tinder is confusing, weird, and often hilarious—at least it is when told by. . . Hannah Orenstein. . . . [A]n addicting story of love lost and found on the dating scene’s latest frontier: the Internet."
—Boston Magazine

"A laugh-out-loud work that singles, marrieds, suburbanites, and urbanites all will clamor for . . . . With an ending twist that will hit readers like a splash of vodka and tonic in the face of their blind date, this novel is one to pack in your beach bag.”
Library Journal

"Charming, funny, and probably all too relatable if you're facing the modern dating scene. Don't swipe left on this story."
—Elite Daily

"A breezy story that will go perfectly with a margarita on the beach . . . . satisfyingly realistic."
—Jewish Exponent

"An engaging tale . . . . you won't be ready to say goodbye."
—DC Refined

"Addictive and zinging, this novel will have your Tinder matches languishing as you rush to the end."
—Read It Forward

"Engaging . . . . A fun, fast read about dating in the city."
Kirkus Reviews

"Playing with Matches is pretty much a novel about what you think your life is like . . . . Hate to break it to you, but ghostwriting your best friend’s text to her boyfriend does not qualify you as a relationship expert, and this novel will help you understand why."

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