Chatting With Hannah Orenstein at Seventeen.com

By Heather Taylor

When Hannah Orenstein was 15, Gossip Girl offered her a path for her life. No, really—it did! The show inspired her to move to New York City, where she attended NYU, took on internships at glossy mags, and eventually wrote a viral essay on the series for Seventeen.com.

Now, Hannah is an assistant features editor at Seventeen.com and author of her first novel, Playing with Matches. Ed got the chance to chat about her career backstory, what it’s like to include “matchmaker” on a resume, and why you should embrace what sets you apart.

Before you got to college, you were already involved in editorial. Can you tell us about that journey?

I started reading J-14 and tabloids when I was 11 years old. I was instantly hooked—I remember scrawling my own edits and ideas into the margins in purple glittery gel pen. I hoarded magazines and started applying to internships at places like Vogue and Elle when I was in high school. A couple editors were kind enough to write back and encourage me to re-apply in a few years.

In the meantime, I launched my own fashion blog and wrote for my school’s newspaper, but I wanted more. I had heard of a site for college women called Her Campus that had just launched a few months earlier near my hometown in Massachusetts. I cold-emailed the editor-in-chief, Stephanie Kaplan Lewis, asking if I could intern for her. I became the site’s first editorial intern, which was the most amazing experience. Because the team was so tiny back then (just the three co-founders, a graphic design intern, and me!), I got to do a little bit of everything: pitching and writing my own stories, watching Stephanie put together the editorial calendar and manage a team of remote writers, listen to the CEO prep for meetings. I felt so energized, inspired, and at home at Her Campus. It confirmed my desire to work in editorial.

For the next three years, I stayed involved with Her Campus, growing from intern to writer to editor to founder/manager of the high school ambassador program. And during that time, the site grew exponentially! I lucked out.

After Her Campus, where did you go next?

I moved to New York in 2011 to study journalism and history at NYU. In college, I interned at Seventeen, the Huffington Post, Mashable, ELLE, and Cosmopolitan.com. I wanted to get experience at different kinds of publications so I could learn what I liked best. I tried to do everything: I became a master transcriber, learned to do crazy-thorough research, and pitched in to do more than what was asked of me. I was a great intern because I focused on making my bosses’ lives easier.

Right before I graduated, I saw a tweet from a Seventeen.com editor I knew from my internship. She said she looking for personal essays written by college students. I pitched one, she published it, and asked me for more. I wrote three more essays for her, and one, “I Based My Entire Life on Gossip Girl and I Don’t Regret It,” went viral. I was asked to apply for the weekend editor position, which didn’t sound ideal to me, because I hoped to land a full-time job. I did the edit test anyway, and did one trial weekend as the weekend editor. That Monday, half the staff called in sick, so the site director asked if I could fill in. Two days later, she offered me a position as a full-time freelance writer at Seventeen.com.

At Seventeen, you cover a little bit of everything, from teen life to pop culture. You also cover relationships, which is made even more interesting because you were once a full-time matchmaker! What was that experience like? 

I spent the summer and fall after my junior year working as a matchmaker for a dating service. I landed there thanks to connections I made during my Elle internship (the matchmaking company’s founder, E. Jean Carroll, is also the magazine’s famed advice columnist). After a few months, I missed the editorial world, and left matchmaking to intern at Cosmo.com.

I felt pretty confident in my resume when I was applying to jobs, but matchmaking was the secret sauce that made me stand out during interviews. Whenever I had interviews—even informational interviews—people would always do a double-take at that line on my resume and ask tons of questions about it.

My background as a matchmaker doesn’t necessarily help me write about relationships, but it did help me build skills that are crucial for a writer to have: asking smart questions, listening well, thinking creatively, using your resources, and building a network.  

When you first got to Seventeen, what was on your to-do list?

At first, I pitched and wrote around eight news stories a day. My beats included entertainment, real girls, sexual health, relationships, astrology, and viral news. Over the past two years, especially after I was promoted to assistant features editor, the job has evolved into writing features, working with freelancers, starring in videos, managing the site’s Facebook and Twitter, live-blogging award shows, dabbling in our prom coverage, and so much more. It’s not just that every day is different—literally no two hours back-to-back will be the same. I love that I’m never bored.

What’s a Seventeen published piece you’re most proud of right now and why?

Pretty Little Liars was a cornerstone of the Seventeen brand for the better part of a decade, so we knew the series finale last month was going to be a big deal for our readers. I spent the finale night holed up in the office with our social media editor and our editorial fellow watching the two-hour episode and live-blogging and live-tweeting the whole thing. I loved putting together this feature on Emison’s babies as the episode was actually happening. That night was such a rush. My heart didn’t stop pounding even after I got on the subway to go home. I loved sharing that moment with our readers and producing stories I knew they’d care about.

Can you tell us more about your novel, Playing With Matches?

Playing with Matches (Touchstone, 2018) is a workplace comedy about Sasha Goldberg, a 22-year-old professional matchmaker for an elite dating service in New York City. Sasha trolls for pedigreed catches on Tinder, coaches clients through rejection and heartbreak, and dishes out dating advice to people twice her age. At first, it’s fun—but balancing the demands of her quirky clients with her own messy personal life quickly gets tougher than she expected. My time as a matchmaker actually inspired my first novel!

What’s your best advice for anyone who wants to get into editorial?

Can I go with lots of small pieces of advice instead? Read EVERYTHING. Like, literally, everything. Figure out what sets you apart. Build a portfolio of clips—freelance stories, stories you pitched at your internship, pieces you wrote for school or your campus blog, pieces you publish on your own blog or TinyLetter. Follow writers you admire on Twitter. Buy your own domain name. Learn how publications monetize and profit. Read about what’s going on the industry (did you know that some reporters only report on media? You’ll learn so much from their work!). Cold-email that writer you love and ask her out for coffee. Learn how to budget, since entry-level editorial salaries tend to be very low. Learn about editorial-adjacent fields like social media, video, and PR, and consider interning in those fields. Don’t be afraid to email writers or editors with questions. Don’t be afraid to try something new and weird, even/especially if you’re not 100 percent sure you’ll be good at it.

You’re an editor extraordinaire, published author, and you also run an amazing Gossip Girl-inspired Twitter account—whew! What are your tips for figuring out how to handle your work/life balance?

I keep a very regular schedule and I multitask (ex: I write my newsletter every Monday night while watching The Bachelor). I schedule in time to hang out with friends and relax. When I feel drained, I turn off my phone, sit in a hot bathtub, drink a glass of wine, and read a book—it’s like the world disappears for an hour.

I’m working on eating green things and going to the gym and staying hydrated, because I’ve heard rumors that these things will make me feel more like a human and less like a zombie. The verdict is still out.

Follow Hannah on Twitter and Instagram.

Photo: Elyssa Goodman

Heather Taylor is a former entertainment writer turned brand mascot aficionado (and head writer) for Advertising Week’s Icon Blog. She shares her thoughts on pop culture at HelloGiggles and has been published in Brit + Co, The Drum, and BettyConfidential. Chat with her about anything from SNL to the Pillsbury Doughboy on Twitter @howveryheather. GIFs highly encouraged.