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.

Introduction

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.