Playing with Matches

A Novel

Playing with Matches

Named a Best Book of Summer by Refinery 29, 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.
  • Touchstone | 
  • 320 pages | 
  • ISBN 9781501178481 | 
  • June 2018
List Price $16.00 (price may vary by retailer)
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Read an Excerpt

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 see more

About the Author

Hannah Orenstein
Photograph by Elyssa Maxx Goodman

Hannah Orenstein

Hannah Orenstein is the author of Playing with Matches and Love at First Like, as well as the dating editor at Elite Daily. Previously, she was a writer and editor at She studied at NYU and lives in Manhattan.