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Hannah Orenstein Is Currently Living Her Best Life After Being Clueless About Her Own Love Life

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Photo credit: Elyssa Goodman

Hannah Orenstein is a former matchmaker, the current dating editor at Elite Daily and author of Playing with Matches. Her first novel was inspired by her experiences as the youngest matchmaker at a top dating service in New York.

The Boston-raised author moved to the Big Apple, where she has happily spent the last 7 years. She began dating during her freshman year of college, which is when she fell hard for a particular guy. Let’s just say he ended up dumping Hannah a few months later.

Hannah’s experiences with dating led her to pitch a dating column to her editor for NYU’s student-run blog. Fast-forward a few years, and Playing with Matches was born.

Learn more about Hannah Orenstein below and make sure to buy her book, Playing with Matches!

Photo credit: Elyssa Goodman

1. What types of books do you enjoy reading in your downtime?

“I love rom-coms, campus novels, stories about women with interesting careers, and thrillers. A few favorites currently on my nightstand: I’ll Eat When I’m Dead by Barbara Bourland, Indecent by Corinne Sullivan, and Hey, Ladies! by Caroline Moss and Michelle Markowitz.”

2. What do you do in your free time when you aren’t writing?

“When I’m not writing, I’m usually reading, splitting a bottle of wine with friends and telling ridiculous stories, exploring New York, or spending time with my family in Maine. I also love watching The Bold Type and Younger with my cat.”

3. What is the main thing you want readers to take away from your book?

“I want to suck readers into the world of matchmaking and keep them entertained. That’s all I can ask for. Beyond that, if this book makes you think differently about love, work, and friendship, or makes you re-evaluate your definition of what “happily ever after” means, that would be wonderful.”

4. If your novel were being made into a movie, whom would you pick to play the lead roles? 

“Cazzie David for Sasha, Ross Butler for Jonathan, AnnaSophia Robb for Caroline, Lacey Chabert for Mindy, and Max Greenfield for Adam!”

5. What has been one of your most rewarding experience as an author thus far?

“It’s been amazing to see readers share photos of Playing with Matches from beaches, pools, airports, and book clubs all across the country and all around the world! I worked on this book for three years on my couch. It’s hard to imagine it out in the world, and I’m so grateful to see that so many people are taking time out of their busy schedule to dive into Sasha’s world.”

6. What motivates and/or inspires you?

“I’m not a morning person at all, but lately, I’ve been motivated to set my alarm for 7 am and squeeze in some writing time at a diner before work. I’ve gotten Instagram DMs from readers asking for a second book… so I’m working on it! In general, I’m always so inspired every time I finish a fantastic book. If another author has laugh-out-loud details or a surprising plot twist, that always makes me curious about how I can incorporate those elements into my own work.”

7. Is there anything you are currently working on that may intrigue the interest of your readers?

“I’m currently in the early stages of a second novel. I can’t say anything about it yet, but I promise that if you loved Playing with Matches, you’ll love this, too.”

8. What advice would you like to pass on to aspiring writers who are struggling with their first novels?

“Get your first draft down on paper as quickly as possible, even you think every single word sucks. You can always go back and edit it later. I gave myself a six-month deadline to write the first draft of Playing with Matches and made it in two weeks under the wire. The draft was pretty terrible! But it existed, which meant I could put it away for a few months, return to it with fresh eyes, and revise it into something stronger, smarter, and more charming. If I worried about making the first draft perfect, I never would’ve finished it.”

Let us know your thoughts on Twitter @emceenetwork and @beautyisacyn!

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Cynthia Sanchez is a student pursuing a bachelor’s degree in public relations and advertising. Born and raised in New York—this passionate journalist enjoys writing about music, entertainment, showbiz news, and much more. She has been interested in the entertainment industry for as long as she could remember. Cynthia intends on working in the entertainment industry one day, and will continue to work her way up until she gets there.

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