Playing with Matches
Page 26
“Really?”
“Really. Until now. Your database access will be turned off today and your clients will be transferred to other matchmakers.”
Penelope rises from the couch and smoothes the front of her purple pencil skirt. Apparently this meeting is now over. She grabs her phone and coffee in one hand and extends the other one toward me. I get up and shake her hand.
“Thank you so much for taking a chance on me,” I say.
I follow her out of the wood-paneled study and past the dining room with the glittering chandelier into the foyer. My interview here feels so long ago.
Penelope opens the door to the brownstone. Outside, I can’t help but laugh. In the past three days, I’ve turned down an engagement, gotten dumped, lost my job, and found another. Nothing feels certain anymore.
I take the steps down to the sidewalk slowly for the last time, running my hand along the beautiful wrought-iron banister. There’s nowhere in particular I need to be, no clients to manage, no boyfriends to call on. For a moment, I don’t know where to go or what to do with myself. But then the solution clicks. My feet carry me to Flower Power, where Caroline is working a shift. As I walk, I flick through the dating apps on my phone and delete them one by one. I don’t need them anymore.
— Acknowledgments —
I’m so thankful for my brilliant editor, Kaitlin Olson, whose vision and attention to detail shaped Playing with Matches into what it is today. I love that she immediately understood and embraced what I wanted this novel to be. Every writer dreams of working with an editor like Kaitlin. Many thanks to everyone at Touchstone Books, including Susan Moldow and Tara Parsons.
Thanks to my fabulous agent, Allison Hunter, whose passion, creativity, and energy know no bounds. I’m so lucky to have had her as my advocate, fairy godmother, and de facto therapist through this exhilarating and occasionally stressful process. Thanks to everyone at Janklow & Nesbit Associates, including Clare Mao for her assistance, and Brenna English-Loeb for changing my life overnight by fishing my manuscript out of the slush pile.
I wrote, sold, and edited this book while at Seventeen.com. Special thanks to all my colleagues, especially Troy Young, Kate Lewis, Kristin Koch, Elisa Benson, and Betsy Fast, for encouraging my foray into fiction and pushing me to grow into a stronger, savvier writer. And thank you to my colleagues at Elite Daily and Bustle Digital Group, including Theresa Massony, Kylie McConville, Kate Ward, and Bryan Goldberg, for celebrating this milestone with me.
Thanks to my mentors: Ann Shoket, who’s always inspired me to dream bigger and work harder, and Kaitlin Menza, whose savvy guidance has shaped my career.
Thanks to my professors at NYU, including Jessica Seigel, whose tenacity and warmth I’ll never forget, and Marie-Helene Bertino, who told me to “keep going” when I turned in a fourteen-page short story about a young matchmaker struggling to make it in Manhattan.
This novel would not exist without E. Jean Carroll, Julia Armet, and the rest of the team at Tawkify. They taught me the magic behind matchmaking; I’m wiser and bolder because of it. I’m also grateful to Melissa Schorr for her column “Dinner with Cupid” in the Boston Globe Magazine, which sparked my interest in matchmaking a decade ago.
Thanks to my friends: Roshan Berentes, Morgan Boyer, Annie Kehoe, Kelsey Mulvey, Elyssa Goodman, Emily Raleigh, Dana Schwartz, Devin Alessio, and Emma and Devon Albert-Stone. They each cheered on my early drafts, gave no-bullshit pep talks on days I was ready to give up, and popped champagne to celebrate when I found success. The heart of this story is about friendship, and I couldn’t have written it without them by my side.
The Orenstein, Hart, and Sykes families are far more functional and wonderful than the families portrayed in this book. Their love and support keep me going. I wish that my grandmother Rose Orenstein, who passed down to me her passions for literature and New York, were here to read this.
My sister, Julia Orenstein, was my first and most trustworthy reader. When I began my first draft, I wasn’t confident in my ability to write a novel, but she always was. Julia’s unwavering enthusiasm for the stories told in this book is one of the most meaningful gifts I have ever received.
One million thanks to my parents, Audrey and Jack Orenstein, who instilled an appreciation for reading and writing in me from a young age, modeled the importance of pursuing what you love, and showed me what drive and determination look like. From suggesting the perfectly cheeky title to editing every draft, their influence is woven into every page of this book.
TOUCHSTONE READING GROUP GUIDE
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Playing with Matches
Hannah Orenstein
— 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 or 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?
— 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 o
r 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!”
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.
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!”
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.
— 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.
— About the Author —
Hannah Orenstein is a dating editor at Elite Daily. Previously, she was an editor at Seventeen.com. At twenty-one, she became the youngest matchmaker at a top dating service. She was born and raised in Boston, studied journalism and history at NYU, and lives in Manhattan with her fat cat, Eloise.
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Touchstone
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This book is a work of fiction. Any references to historical events, real people, or real places are used fictitiously. Other names, characters, places, and events are products of the author’s imagination, and any resemblance to actual events or places or persons, living or dead, is entirely coincidental.
Copyright © 2018 by Hannah Orenstein
All rights reserved, including the right to reproduce this book or portions thereof in any form whatsoever. For information, address Touchstone Subsidiary Rights Department, 1230 Avenue of the Americas, New York, NY 10020.
First Touchstone trade paperback edition June 2018
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Interior design by Jill Putorti
Cover art by Sinem Erkas
Author photograph by Elyssa Maxx Goodman
Library of Congress Cataloging-in-Publication Data
Names: Orenstein, Hannah, author.
Title: Playing with matches / Hannah Orenstein.
Description: First Touchstone trade paperback edition. | New York : Touchstone, 2018.
Identifiers: LCCN 2017037051 (print) | LCCN 2017048167 (ebook) | ISBN 9781501178504 (eBook) | ISBN 9781501178481 (paperback)
Subjects: LCSH: Dating (Social customs)—Fiction. | Mate selection—Fiction. | GSAFD: Love stories.
Classification: LCC PS3615.R4645 (ebook) | LCC PS3615.R4645 P58 2018 (print) | DDC 813/.6—dc23
LC record available at https://lccn.loc.gov/2017037051
ISBN 978-1-5011-7848-1
ISBN 978-1-5011-7850-4 (ebook)