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Taking a swipe at love, as told by this Needham native

Hannah Orenstein, author of “Playing with Matches.”Elyssa Maxx Goodman

In 1993’s “Sleepless in Seattle,” Annie Reed falls for Sam Baldwin after hearing him on the radio, and decides to write him a letter. Kathleen Kelly and Joe Fox of 1998’s “You’ve Got Mail” first met in an online chat room. Today, in an age when people score dates by swiping through hundreds of potential matches with their fingertips, it only makes sense for apps like Tinder to be part of romantic comedies, says Hannah Orenstein, Elite Daily’s dating editor.

Orenstein’s debut novel, “Playing with Matches,” hit shelves last week.

“I really wanted to write a romance that involves dating apps because that’s just how me and my friends were dating,” said Orenstein, who grew up in Needham. “You can’t really write a millennial love story without focusing on dating apps in some way, and so it felt really gratifying to me to include that in my own novel.”


Orenstein’s “millennial love story” follows Sasha Goldberg, a woman in her early 20s who, like Orenstein, studied journalism at New York University and finds herself working as a professional matchmaker for a dating app in New York City.

Orenstein has never been employed by a matchmaking app, but she has worked as a matchmaker for a dating service. She also created her own matchmaking newsletter in college — one she modeled after The Boston Globe’s “Dinner with Cupid” column, in which two people are set up on a blind date and then share their post-date reflections. Orenstein said she grew up reading “Dinner with Cupid” every Sunday with her dad, and they continued the tradition after she moved to New York.

In “Playing with Matches,” Sasha falls for — you guessed it — a guy she meets on Tinder, breaking her company’s rule against becoming romantically involved with the people they set up with clients.


Orenstein said that while Sasha’s experiences as a matchmaker veer off course from her own reality, she did draw inspiration for the book from her matchmaking days.

“We both started working as matchmakers very young and felt in over our heads,” Orenstein said. “[We were] both juggling a lot of interesting romantic adventures while trying to find love for other people and feeling really not confident in our own love lives.”

In addition to entertaining bartenders and servers at trendy restaurants, dates planned through apps are a perfectly legitimate way to meet a romantic partner, Orenstein said, and she wanted to depict that in her book.

“I think [dating apps are] a continuation of how people have always met,” Orenstein said. “My parents met at a Jewish singles’ mixer, and I’ve been to that same mixer, called the MatzoBall … and when I first went, I had been on dating apps for a couple years at that point, and my only comparison was like, ‘This feels like Tinder in real life.’”

While young people who grew up with the Internet may have the upper hand at navigating dating apps, Orenstein said “Playing with Matches” can appeal to people who have yet to swipe right, too. After giving a copy to her uncle who’s in his 50s, she said she was pleasantly surprised by his reaction.

“He is on dating apps and dating sites, and he got a really big kick out the book,” Orenstein said. “He was like, ‘These lessons in the book are universal. … Don’t count out readers like me.’”


Orenstein will read from “Playing with Matches” and have a conversation with Stephanie Kaplan Lewis, the editor in chief of Her Campus, at Porter Square Books on July 17.

Kaitlyn Locke can be reached at Follow her on Twitter at@ke_locke.