Book Review: Playing with Matches by Hannah Orenstein

Sasha, a twentysomething recent college graduate in New York City, lands a job with Bliss, an elite matchmaking service, after an impassioned speech about love and love gone wrong. Her experience with relationships began as she watched her parents marriage implode at a young age, though she now realizes the chance for success is low between a desperate man and a Russian mail-order bride. But it is this very thing that sets her apart from other Bliss applicants and makes her believe she could really make a difference as a matchmaker.

Bliss sounded like the opposite of the way my parents met. Bringing two people together based on a hunch 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 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 guys who handed Mark Zuckerberg his first beer at Harvard, then casually slipped him my business card: Sasha Goldberg, Matchmaker.

Sasha’s new boss, Penelope, wastes no time in throwing her right into the dating scene with her first client Mindy and she quickly realizes how much has changed in the years she has spent by the side of her boyfriend Johnathan, a quintessential workaholic up-and-comer in the New York financial district. So she turns to her best friend and serial dater Caroline to introduce her to the endless number of dating apps and sites she is expected to glean for potential matches.

It is through Tinder that Sasha meets Adam, a seemingly perfect match for Mindy, though she cannot deny the chemistry between them when they first meet. However, rule number one at Bliss is no dating the recruits, which Sasha need not worry about as she is happily taken. That is until Johnathan’s late nights at the office turn out to be something more and Sasha finds out what is truly means to be single in New York. When she eventually crosses that imaginary line with Adam, Sasha is forced to reevaluate her position at Bliss and what it is she truly wants from her life which is beginning to look quite different from what she had ever imagined.

What follows is a quirky romance paired with personal revival as Sasha attempts to find her place within the fast-paced world of matchmaking both as a career and in her own personal life. Written with humor and heart, Playing With Matches draws from the author’s own experiences with her first post-college job and explores the myriad ways uncertainty and success can bleed into the rest of our lives. Shasha’s story follows a jagged trajectory that serves to illuminate how the discordant moments in life ultimately come together at just the right time to lead us down the path meant for us.

“Matchmaking is the most powerful job a person can have,” she muses. “Think about it, what so people really want in life besides love? Success? Maybe. Fame? Not really. Let’s say you go to a party and people ask you 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 se them up, give them advice, teach them what they’re doing wrong. You’ll see. That power is transformative.”


A review copy of this title was provided by Touchstone Books.



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