Hannah Orenstein: On a Day in Her Writing Life, Working at Elite Daily, First Drafts and Her New Novel, "Meant to Be Mine"
I’ve been following Orenstein’s colorful life on Instagram via @hannahhhorens for a few years now, and her posts have been a constant source of inspiration, encouragement, and writing advice. On Instagram, Orenstein has shared info on her writing process, including how she sometimes enjoys writing longhand, as well as the publishing process. Her transparency of the author’s journey is refreshing and relatable.
I recently interviewed Orenstein in the exciting wake of her new book that launched this week, Meant to Be Mine, a part romance, part multi-generational story that follows Edie Meyer, a 29 year old woman who reaches the day her grandmother, Gloria, predicts Edie will meet her soulmate, and Grandma has never been wrong. Of course we all know that life can’t always be that easy, and Edie encounters some challenges along the way. Meant to Be Mine has generated a lot of excitement from authors and readers alike, so you should definitely grab a copy.
I wanted to speak to Orenstein on some of the highlights of her journey, influencers, challenges, and a few other fun questions.
When did you first become interested in writing? What events led to you deciding to write your debut novel, Playing with Matches?
I've always loved to write since I was a little kid, but I didn't take the idea of fiction seriously as a career until I was older. I went to college to study journalism, hoping to work in magazines after graduation. I had a brief detour working as a matchmaker for a dating service before I landed my first magazine job at Seventeen, and that inspired my debut, Playing with Matches. It's a rom-com about a recent college grad who works as a matchmaker in New York City right around the time that dating apps begin to really explode in popularity, the struggles and oddities she faces while setting up her clients, and her own rollercoaster of a love life.
How would you describe your creative process? I.e. coming up with the idea, writing the first draft, etc.?
With this novel, I knew that I wanted to write something that explored a big, existential question, which turned out to be: Would you want to know the exact day you'd meet your soulmate? I also had a few other things in mind at the time: It was the early days of the pandemic, so I wanted to write something that felt vibrant and glamorous, like an escape, and I wanted to write about a grandmother-granddaughter relationship (and instantly, the character of Gloria felt so vivid, I could hear her one-liners). I outlined heavily and then wrote the first draft within six months. I like to give readers a peek into my process behind the scenes, so as I write, I'm constantly sharing updates about how it's going on my Instagram Stories.
Can you explain your experience with publishing a novel? What were your emotions throughout the process?
I feel so incredibly grateful for readers' support. Without their enthusiasm, I simply would not be able to live out this dream. Period! Publishing a book is a lot of work — even after you finish the final draft, there's a lot that goes on in terms of publicity and marketing — but it all feels worth it when you get to hear from readers and even meet them at events.
Do you ever let your characters take you where they want to go, or do you have a set plot that you don’t deter from?
I stick to my outlined plot, but that outline can change a lot before I dub it "final." With this book, I had a few elements that I kept switching around — who Edie meets on her predicted date, what the tragedy in the middle of the book would be, and how it ended — and it took me a while to figure out exactly how I wanted things to play out.
Are your characters ever based on real-life people? If so, do you ever project your own identity into your characters?
Some are, yes! In this book, Gloria is very much inspired by all four of my grandparents, and I imagined Kiara as a cross between Alexandria Ocasio-Cortez and Lauren Duca. But of course, elements of my own personality and my own personal interests seep into the book in various ways. If readers follow me on Instagram, I bet they can catch a few of those crossovers.
From following along with your Instagram, I noticed you have been writing longhand. What prompted you to do that?
I wanted to be less tethered to my laptop and be able to write outside in the summertime. Elin Hilderbrand writes longhand and so I wanted to give that a try. I wound up loving it. There's something very freeing about just having to keep putting words down on the page; you can't delete lines and rewrite them repeatedly.
What’s the longest bout of writer’s block you’ve had? How did you overcome it?
After I finished my first book, I had a really hard time coming up with the right idea for my second. The road to publishing a first book is harder than the road to publishing any follow-up, so in some ways, it felt like I had achieved something major (just landing a book deal, period, to say nothing of the quality or the success!) and was afraid I wouldn't be able to replicate that feat. I kept pitching ideas to my agent, and writing sample chapters, and nothing was really clicking. Ultimately, I discovered all these hugely Instagram-famous jewelers and was totally fascinated by their work and their lives. I also knew that I was interested in writing about the impact social media has on our relationships. Together, those two ideas led to Love at First Like, a rom-com about a jewelry store owner who fakes her own engagement on Instagram in order to save her business. There's no trick to getting over writer's block, but staying curious is essential. That's how you stumble across new things that intrigue and inspire you, and those are always the best ideas.
Where do the ideas from your novel come from? I.e. dreams, people, experiences, interests, etc.
Each book is a chance to dip into a different world. With Playing with Matches, I was inspired by my own experience working as a matchmaker, and my interest in the dating industry as a whole. I wanted to take readers behind the scenes of that world. Love at First Like came from my interest in jewelers and social media. Head Over Heels, my rom-com set in the world of Olympic gymnastics, was inspired by the 15 years I spent as a gymnast during my childhood and my fascination with how elite athletes navigate life after leaving their sports. Meant to Be Mine originated with that single question — would you want to know the exact date you'd meet your soulmate? (I initially thought I'd want to know, but as I wrote the book, I changed my mind.)
How much research goes into writing a novel?
It depends! I like to do a few interviews and have some experts on call. For Meant to Be Mine, I interviewed a fashion stylist in New York City, since that's exactly who my protagonist is. I wanted details about what that career really looked like. I already knew a fair bit about the fashion industry (having interned for a womenswear designer and several fashion magazines, and having written about the fashion industry as a journalist) but that interview took my knowledge a step further. There's also a political plot line in the book, and speaking to a campaign organizer was incredibly insightful. I also had a small roster of family and friends with expertise in various fields (everything from indie rock music to cardiology!) who were kind enough to give me insight as I needed it.
How do you know when to stop writing? Do you have an outline of the characters or the plot first?
Like I said, I outline before I write the first draft, so it's easy to know when I've hit the end. I sort of outline the plot and characters at the same time, or at alternating times, as ideas come to me in pieces.
How much does living in NYC affect your stories?
Very much so! This is my second novel set in my neighborhood — Williamsburg, Brooklyn — and my third set in the city. I want my books to transport readers somewhere new, so I pack in lots of descriptions and details of real places: restaurants, bars, parks, and more. The city has a lot of natural characters and I'm constantly wishing I had more time on my hands so I could write about them all.
You currently work full-time at Elite Daily – what is it like juggling this along with writing, dating, friends, family, etc.?
Busy! I'm a big believer in routine and that helps the juggling feel less chaotic. I wrap up my Elite Daily work at six every day, write mostly on weekend mornings and afternoons, and fit in dating, friends, and family around that. It's also really important for me to schedule some down time where I'm just reading books or the paper.
Describe a day in the life of Hannah Orenstein.
9 am: My day starts at Elite Daily. I like to have a caramel latte from Dunkin Donuts while I scan the internet for what's going on and catch up with the editors and writers on my team.
2 pm: After editing some stories and looking at our traffic, I usually have a few meetings.
6 pm: Lately, I've been recording podcasts and doing interviews to promote the book.
7:30 pm: I recently joined an amazing yoga studio, and to unwind, I'll take a class, then read in the studio's backyard hot tub.
9:30 pm: I'll grab a slice of my favorite hot honey pizza on the walk home.
11:00 pm: One or two old episodes of RuPaul's Drag Race and I'm ready for bed.
Out of the entire process (idea to execution to publishing), what’s your favorite part?
It's a tie between the excited jitters of just beginning to piece together a new idea and feely really deeply immersed in writing a first draft. Editing challenges me the most, and promotion is a lot of fun.
What’s your all-time favorite book? Favorite genre?
What a question! I can't pick just one, so I'll go with 28 Summers by Elin Hilderbrand, Red, White & Royal Blue by Casey McQuiston, Detransition, Baby by Torrey Peters, and The Invisible Life of Addie LaRue by V.E. Schwab.
Is there a specific book or person that you can credit your inspiration to?
I've always been an avid reader, but I often think of my grandmother, Rose, who grew up in a small farm town in rural Pennsylvania during the Great Recession. She loved to read as a little girl, but her town's entire library only took up a single shelf. That really stuck with me as a kid — how lucky I was to have nearly unlimited access to all kinds of books. (Also, Rose's childhood neighbor was E.L. Kongisburg, who grew up to write The Mixed Up Files of Mrs. Basil E. Frankenweiler. Two of the characters in that book are named after my uncles. I never met her, but maybe the idea of having a working novelist well within six degrees of separation planted a seed of inspiration for me.)
What piece of advice would you give to aspiring writers today?
Set a deadline to finish your draft and force yourself to stick to it. Maybe you track your weekly word count goals in a spreadsheet, or you share your progress publicly on social media — whatever you need to do to hold yourself accountable. Finishing the first draft is the most daunting step, but it's also the most important!
Hannah Orenstein is the author of Playing with Matches, Love at First Like, and Head Over Heels, and is the deputy editor of dating at Elite Daily. Previously, she was a writer and editor at Seventeen.com. She lives in Brooklyn.
About the Interviewer
Laura Beth Eason is an aspiring author, lifestyle blogger, and editor living in Raleigh, NC, and has also worked in English education. She is an alumna of The University of North Carolina at Charlotte and holds a B.A. in English Language and Digital Technology. Laura has a passion for mental health awareness, is a proud lover of the romantic comedy genre, likes dessert over dinner, and is a wine connoisseur. You can read her blog at https://essential-eloquence.com/ and find her on Instagram @laurabetheason
