Match Made in Manhattan: 9 Questions With Playing With Matches Author Hannah Orenstein

Hannah Orenstein (Photo credit: Elyssa Maxx Goodman )

Hannah Orenstein (Photo credit: Elyssa Maxx Goodman)

By Lindsey Wojcik

In her delectable debut, Playing With Matches author Hannah Orenstein exquisitely illustrates the post-collegiate New York experience. The protagonist Sasha Goldberg contemplates where her friendships, relationship, and career will take her after graduating from New York University with a degree in journalism.

As is often the case, Sasha’s path isn’t linear. At 21, she does not land her dream a job and instead takes a gig as a matchmaker for an elite New York dating service, where she quickly learns to navigate the matchmaking formula. To her surprise, it involves lots of Tinder swiping on behalf of clients and meticulous coaching. She also learns that in order to be successful, she has to be bold.

She’s hopeful that her clients will find the love she believes she has with her boyfriend Jonathan, a workaholic finance-bro. However, when Jonathan betrays her, life becomes messy and she has to find a way to balance her personal and professional lives.

Playing With Matches (out June 26) is a perfect summer read. Orenstein recently answered my questions about her experience as a young matchmaker, dating trends in 2018, and how she found her voice writing fiction after many years with journalism experience.

Lindsey Wojcik: What enticed you about being a writer? Did you always want to write or did something specific inspire you to pursue it?

Hannah Orenstein: I’ve never been able to imagine doing anything else. As a kid, I filled up notebooks with short stories and attempts at novels, mostly written in purple glitter gel pen, because I thought that was cool. When I started studying journalism in college and interning at magazines, I lost confidence in my ability to write fiction; I thought journalism was more my route. I wound up taking a fiction workshop during my last semester of college, and that’s where I wrote a short story about a young matchmaker in New York that ultimately became the basis of Playing with Matches.

LW: Who influenced you early on and who continues to be a source of inspiration?

HO: I’ll never forget reading The Royal We by Heather Cocks and Jessica Morgan. The voice was perfectly dishy, relatable, and funny, and the protagonist was a young woman. That was the first time I thought, "Wait a sec, maybe I can do this whole novel thing." There are so many writers that inspire and influence me in addition to Heather and Jessica, but to name a few: Ann Shoket, Georgia Clark, Jo Piazza, Camille Perri, Dana Schwartz, Amy Poeppel, Andrea Dunlop, Tara Isabella Burton, Jessica Knoll, and Lauren Weisberger. 

LW: What intrigued you about matchmaking and how did you become one of the youngest matchmakers at a top dating service?

HO: I grew up reading a blind date column called “Dinner with Cupid” in the Boston Globe magazine every Sunday with my dad. Essentially, two people are set up on a blind date, and the magazine runs side-by-side interviews with each person following the date. I loved the column so much that I ran my own version for my college’s blog. While I was working on the column, I was also an intern at ELLE. The famed advice columnist E. Jean Carroll also happens to run a matchmaking service. E. Jean is one of my biggest writing heroes, and so when I got the chance to work on a project for her—transcribing a four-hour interview with Erica Jong, it was truly incredible—I told her that I dabbled in matchmaking a little bit. She hired me on the spot. I already had plans to study abroad in Paris, so I’d wake up in the middle of the night to Skype into matchmaking training sessions, which were held at normal hours in New York—but at 2 a.m. my time! Once I got back to New York that summer, I began working full-time as a matchmaker. I was 21, desperately trying to help clients in their 30s, 40s, 50s, and beyond fall in love! 

LW: In addition to matchmaking and writing novels, you’re the dating editor at Elite Daily. It seems like how people date and pursue relationships is constantly evolving. What are some trends that you’re keeping your eye on right now and did any of those trends influence the relationships in Playing With Matches? 

HO: If you're a dating in 2018, you’re likely using dating apps. So it was really important to me to weave the experience of using dating apps into Playing with Matches. My characters have meet-cutes involving Tinder, toggle between multiple dating apps, and at times even feel their thumbs cramp up from swiping all day. 

The other trend, of course, is matchmaking itself. I think people imagine matchmakers to be really old-fashioned, like something you’d see in Fiddler on the Roof. But the truth is that matchmaking services are huge today, especially in big cities. For the subset of people who already hire trainers to help them work out at the gym and send their laundry out, why wouldn’t they outsource dating to professionals, too?  

LW: How do your experiences as a matchmaker compare to what Sasha goes through in Playing With Matches?

HO: Our experiences are similar in a lot of ways. Like Sasha, I was the youngest matchmaker at an elite dating service in Manhattan. I worked one-on-one with clients to find and vet potential matches and set up dates at cool spots. At the time, I was just 21, and I felt so incredibly out of my league. I wanted to help my clients find successful dates and satisfying relationships, but I was still learning what all that meant for myself. Sasha deals with that same kind of impostor syndrome. That said, her character isn’t me. My life isn’t quite interesting to hold up as a novel—but that’s what fiction is for. 

LW: When you were writing Playing With Matches, was there something in particular you were trying to connect with or find?

HO: I wanted to write exactly the kind of book I prefer to read: A juicy love story revolving around a protagonist who cares deeply about her career, her friendships, and her family. I knew I wanted to set the book in downtown Manhattan, where I was living. I hoped it would be the kind of book that made readers feel seen and understood—especially young women. 

More specifically, I wrote the first draft the summer after I graduated from college. I wanted to write something that captured the tiny joys and anxieties and comforts of being 22 years old and sitting on a ratty old couch with your best friend while swiping through Tinder, drinking wine from the sale rack, and worrying about chasing down your dream job. There’s a lot in the book that’s more glamorous, exciting, and high-stakes than that, but those scenes are close to my heart because they feel the most relatable, in my opinion. 

LW: How did your journalism career prepare you for writing and publishing fiction?

HO: Good writing is good writing, no matter the form. I had a tough time finding the voice that came naturally to me as an author. I worried that my voice wasn’t “fancy” or “serious” enough. My style is pretty simple, with the occasional joke thrown in. I think that’s a direct result of studying journalism. My professors hammered home that you don’t need to get flowery to tell a story in a compelling manner. All those years I spent honing my voice in journalism school and later as a working writer definitely helped me develop an authentic sound. 

LW: What’s next for you? 

HO: Right now, I’m really excited to celebrate the launch of Playing with Matches with events in New York, Boston, and Washington, D.C. Beyond that, I’m exploring options for bringing the book to TV. Next up, I’d like to write a second novel. 

LW: What’s the best advice you’ve received and what’s your advice for up-and-coming writers? 

HO: My favorite piece of advice comes from my former boss, E. Jean Carroll. She used to tell us matchmakers, “Fortune favors the bold.” I think about that advice often—it inspires me to take risks and put myself out there. 

For aspiring novelists who have yet to begin their first drafts, I’d suggest this: Marinate in your idea for awhile. Obsess over it while you’re in the shower and commuting to work. Map out the main points of your plot, ask yourself questions about your characters, and write an outline if that’s your style. Once you’ve gathered enough information to write the first chapter, get going. I gave myself a strict deadline of six months to write the first draft, and that really helped me prioritize writing on days when I wasn’t totally feeling it. 

To learn more about Hannah Orenstein, visit her official website, like her Facebook page, or follow her on Twitter and Instagram.