The Real Life Carrie Bradshaw: Meet Dating Editor And Author Hannah Orenstein
She's a dating editor. She was a matchmaker. She lives in the Big Apple in an apartment decorated so well it looks like it belongs to one of your favorite New York City TV characters. And she's publishing her first novel, Playing With Matches, a story inspired by her own experience as a matchmaker. Comparing Hannah Orenstein to Carrie Bradshaw is easy. But illustrating the remarkable success she is in her own right? Well, let's just call it inspiring.
By day, Hannah is Elite Daily's resident Dating Editor, a role she took on after being the Assistant Features Editor at Seventeen.com and many semesters of interning at some of the most renown women's media brands in the world. During her college years at New York University, she spent a summer as a matchmaker, enhancing the dating lives of Manhattan residents. It was that experience that inspired Playing With Matches.
Read on to learn how she turned her passion for writing and relationships into an extraordinary career.
Let’s go to back the beginning. Were you always passionate about writing and relationships? What sparked those interests?
My earliest memories are writing short stories in marble composition notebooks with glitter gel pens and orchestrating fake “weddings” with my teddy bears. So, yeah! I guess I’ve always had interests in storytelling and love. Those interests have been pretty consistent, though they’ve evolved over the years.
Why did you decide to come to New York for college?
I was itching to move to New York. In high school, I’d take a bus to New York once a month, stay with family in Brooklyn, and spend the weekend exploring the city. I knew I wanted to live here forever, so why wait until after college?
What was it like to go to college in New York? How did that impact your career?
I didn’t feel like a college student in New York; I felt like a New Yorker who happened to take classes. For me, that was perfect. I organized my classes so I could intern for two or three days a week. I learned more during those internships than I did during my journalism classes — hands-on learning was the best way I could have possibly prepared for a career. I met my two closest, most valuable mentors at Seventeen; a connection I made at ELLE led to my stint as a matchmaker, which inspired my book; my semester at Cosmo.com taught me everything I needed to know about writing for the internet. Going to college in the city gave me access to internships that changed my life. It was a huge privilege.
You interned at very impressive media brands. What’s your secret for landing the internship and standing out once you start?
The reality is that the industry is an incredibly different place than it was just a few years ago. Those internships I mention above that jump-started my career? Those opportunities don’t exist in quite the same way today. Hearst (which owns those publications) no longer hires interns; instead, they have a smaller, more competitive roster of fellows who are paid very low wages. So, first off, I really urge aspiring writers to look realistically at the industry and understand that your path to a job may not look anything like the paths of people who came before you — and that’s OK!
I would recommend seeking out internships on Ed2010 and Indeed.com instead of solely relying on your school’s career center. Follow editors you admire on Twitter and Instagram and engage with their content so they know who you are (and make sure that your own social media is up to par).
If you want to write and edit, work for your school’s newspaper or blog, pitch freelance pieces to sites you like, and collect the clips you’re most proud of so that you can send them as work samples when you apply for internships.
And don’t be afraid to think outside the box. OK, so you might not intern at Vogue. But can you intern for your local paper? Or intern in a site’s social media department or video department? It’s so important to keep an open mind and be flexible instead of giving up when you don’t get that one coveted opportunity you’ve always dreamed about.
After you graduated from NYU, you started as a writer for Seventeen.com, and I love the story for how that role came about. Would you give us some background?
A month before I graduated, I spotted a tweet from a Seventeen editor I knew who was looking for personal essay pitches from college students. I emailed her some ideas and wound up being assigned a few of them. One was called “I Based My Entire Life on Gossip Girl and I Don’t Regret It.” It was an essay about how my deep love for Gossip Girl helped me figure out a life path when I was 15 years old and — like so many teens — feeling majorly lost about who I was and who I wanted to become. It went viral to the point where British tabloids mocked me and (three years later!) my Instagram DMs are still filled with messages from Gossip Girl fans from around the world.
Based on the success of that essay, Seventeen.com’s site director asked me to apply to be the weekend editor. I wasn’t that thrilled about that prospect because I was hoping to land a full-time role somewhere. But I figured it wouldn’t hurt to apply. I did a trial run over July 4th weekend. That Monday, someone on staff called in sick, and so I was asked to fill in for the day. Two days later, I was offered a position as a full-time freelance writer, and I took it.
You wrote so many standout pieces for Seventeen during your time there. Was there one or a series of articles that you felt especially connected to?
First off, thank you! My favorite part of my job was bringing teen girls’ stories to life. I worked as a ghostwriter for personal essays, and it was such an honor to tell those girls’ stories. Some memorable favorites were “I Gave Up College to Get Married — Now I’m 19 and Divorced,” “I’m 19 Years Old and Raising Two Teenagers,” and “Convincing My School to Change Its Sexist Dress Code Helped Me Discover I’m Agender.”
I was also really passionate about writing guides that hopefully empowered readers to feel more in control of their sexual health. I did a lot of stories about birth control, safe sex, STIs, and consent. That work felt really satisfying to me, especially in a time when abstinence-only sex ed is common and only 13 states require their schools to teach medically accurate sex ed.
You became the Assistant Features Editor for Seventeen.com, and you published articles on everything from relationships to celebrity news to personal essays. What is your advice for succeeding in a role so that you can get to that next step in the company?
Don’t be afraid to have honest conversations with your boss about what your goals are. Even if you get shot down for a promotion or raise once, you should still continue to advocate for yourself. And whenever you get a chance, ask your boss for concrete feedback on areas where you can improve, because that’ll make you a better worker now and a stronger candidate for jobs in the future.
(This is a #HearstElevatorSelfie!)
Did writing about relationships for Seventeen inspire you to take an even deeper dive into the world of dating content?
Definitely! I was writing about crushes, relationships, hookups, prom dates, and sexual health, and I found I really enjoyed that work. I loved writing for teens, but I was ready to make a change and write for slightly older readers.
After Seventeen, you became the Dating Editor for Elite Daily. That second job can often be tricky because you’re trying to start to pave a career path. What made you decide to specifically become a dating editor?
I started writing about dating in college. I had a column on my school’s blog called “Now Kiss,” in which I’d set up my classmates on blind dates and write about their experiences. A year after I launched the column, I pitched myself to the founder of a professional matchmaking service in New York, and she hired me on the spot. I started working full-time as a matchmaker when I was 21, during the summer after my junior year. That job became the inspiration for Playing with Matches.
So, between writing about sexual health at Seventeen.com, working as a matchmaker, and writing a book about twenty-something girls who are in complicated relationships and swiping through dating apps, I felt like I could bring a pretty well-rounded perspective to my role as a dating editor. When I heard Elite Daily was hiring, I was thrilled!
What does it look like to be a dating editor?
I work with a team of hilarious, smart, savvy writers to create stories about single life, dating, dating apps, relationships, breakups, sex, and sexuality. It’s my dream job.
You’ve had an article you wrote about yourself go viral, and that had some positive and negative repercussions. Tell us about that experience and how you learned to deal with internet trolls.
I’m lucky that the response to the Gossip Girl piece was mostly pretty positive. But other pieces I’ve written have led to avalanches of hateful tweets, Instagram comments, and emails — I’m talking about incredibly appalling, anti-Semitic death threats and rape threats after expressing slight criticisms of certain celebrities. I won’t lie, those experiences are draining and hurtful. And I know that other writers, especially writers of color and LGBTQ+ writers, have it much worse.
Okay, let’s talk about your new book! What was the inspiration behind Playing With Matches?
I was searching for a novel that captured exactly how I felt in my early twenties — the crushing sensation of impostor syndrome that comes along with your first job, how dating can feel both exhilarating and exhausting, and how comforting it is to drink cheap wine and swipe around through Tinder with your best friend. I couldn’t find one that summed up all of those things in a way that felt relatable to me. So I wrote it myself. I also wanted this novel to illuminate what it’s really like to work as a matchmaker. And finally, I wanted this book to be a love letter to all my favorite places in New York. The city changes so rapidly, but I think this is a pretty accurate depiction of what life was like for a certain group of people in downtown Manhattan during the summer of 2015, when I wrote the first draft.
@danaschwartzzz always knows the right thing to say, so I’m just stealing her ridiculously kind IG caption: “The first time I met @hannahorens, we sat on barstools in Manhattan and revealed that we were each working on novels. Our friendship continued through writing dates in Brooklyn and I saw this brilliant, hilarious, deeply clever and devastatingly true to life novel come into the world in real time. Everyone should read it, immediately.” 📷: @danaschwartzzz 😍
Can you give us a glimpse into the process of writing a novel?
If you’re writing fiction, you have to complete the entire manuscript and whip it into pretty good shape before an agent or editor will even consider working with you. So I spent a few months daydreaming about characters and plot, wrote myself an outline of each chapter, and then set a six-month deadline for writing the first draft. After that, I spent almost another year editing and revising. Next, I queried agents, which means emailing agents sort of a cover letter about your book along with the first few pages. Once I signed with my agent, I worked on two rounds of revisions with her, and then she submitted the book to about 20 editors for consideration. One of them loved Playing with Matches and offered me a book deal! That was 16 months ago; since then, we’ve been editing, selecting a cover, and working with my publisher’s talented marketing and PR departments.
You wrote Playing With Matches while you were working full-time as an editor. How did you manage your free time to make this huge goal happen?
I started writing after I graduated college, before I had a full-time job! I spent hours a day applying to jobs and freelancing to make some money, but I still had more free time than I knew what to do with. So I wrote the book. I couldn’t foresee a period in my life where I’d have that much time to write fiction ever again, so it was important to me to write as much as possible. I had about 100 or 150 pages down when I got my job offer at Seventeen.com. I wrote the second half of the book mostly on weekends. As much as I wanted to write after work, my brain felt fried from writing eight or nine hours a day at my job. I couldn’t string together sentences by the time I could home.
By the time I hit 50 pages, I couldn’t imagine abandoning the project. It was like, you’ve come this far, why give up now? Keeping that thought in mind gave me the motivation I needed to finish writing the book.
So much dedication and hard work went into this book. What do you hope readers take away from it?
I hope you’re entertained! That’s all I can ask for. Beyond that, I hope you’re transported into a believable world in which you learn something new about matchmaking, love, friendship, or New York. There’s a big twist at the end that sends a strong message about how I personally feel about dating in your early twenties, and I hope that resonates for some people.
Finally, I’m obsessed with the cover. Pardon my bragging, but it’s pink and pretty and punchy and looks amazing on Instagram. It’s already all over my feed. I wouldn’t be mad if it was all over yours, too.
Behind the Scenes
What books are you reading this summer?
- Choose Your Own Disaster by Dana Schwartz
- Social Creature by Tara Isabella Burton
- The Bucket List by Georgia Clark
- Charlotte Walsh Likes to Win by Jo Piazza
- Hey Ladies! by Caroline Moss and Michelle Markowitz
I can’t remember the last time I’ve read a book by a man.
If you could brunch with your favorite fictional character, who would it be?
Honestly? Sasha and Caroline from Playing with Matches. When I finished the final draft, I felt sad because I didn’t have their voices bouncing around in my head anymore. I miss them! And I bet they’d take me to a killer brunch spot.
Who is on your power playlist?
Britney Spears, Betty Who, and the Gossip Girl soundtrack.
What place in New York City inspires you the most?
Washington Square Park! The closest thing NYU has to a campus. There’s nothing better than listening to live music on a sunny afternoon in that park.
Four years ago, I moved to New York. That anxious, wide-eyed freshman grew up. I have to thank the best city on the planet for teaching me how to hail a cab, navigate the subway, locate pizza in any neighborhood after 3 am, keep a cat alive, write, find $6 Chinese takeout that does not give me food poisoning, go from intern to writer at my favorite magazine, fend off cat-callers, get everything (drinks, plane tickets) for free, fall in love, and transform my friends into family. New York, you'll only see the last of me when I'm carried out in a casket.
Do you have a personal mantra?
Fortune favors the bold. I first heard that from my matchmaking boss, E. Jean Carroll, who also happens to be the incredibly wise advice columnist at Elle. That phrase always gives me the push I need to take a risk and put myself out there.