Before Hannah Orenstein became a women’s lifestyle editor and a published author with five books under her belt, she was navigating the wild world of post-grad life in New York City — juggling internships, deadlines, and, unexpectedly, a job as a professional matchmaker. The gig wasn’t glamorous, and it definitely wasn’t her dream job, but it ultimately launched her into the writing career she hadn’t yet imagined for herself.
“Zero marriages, zero relationships, zero situationships — like, I did absolutely nothing right,” Orenstein tells Her Campus about this time in her life, laughing. “But I really credit that job for helping with my career, even though it was in a totally different field.”
The gig happened upon Orenstein after she met E. Jean Carroll, the famed writer and advice columnist who had just started a matchmaking company. “She’s such a fantastic writer, and I was obsessed with her, dating back to high school,” Orenstein says. “So when the opportunity came up, I was like, I would be an idiot to pass this up.” So, Orenstein spent a summer working as a matchmaker, thrown into a role that forced her to show up with confidence, even when she felt completely out of her depth. “At an internship, you’re expected to just be learning the ropes,” she says. “But here was a job where I really had to push myself because I was supposed to help someone find the love of their life.”
The job didn’t result in any romantic success stories, but it gave her something even better: a beat. “At my job at Seventeen, my editors were always like, ‘If there’s a story about dating, love, sex ed — give it to Hannah.’” That beat would go on to influence her entire career, from her editing roles at top media companies to her work in fiction.
These days, Orenstein is the deputy lifestyle and wellness editor at Bustle and the author of five novels, with her latest, Maine Characters, hitting shelves May 13. “This one is about two half-sisters who meet for the first time as adults after their father dies,” she says. “I’m calling it a grown-up Parent Trap — it’s messy, complicated, and I’m really excited about it.” She’s already working on a follow-up that digs deeper into the same genre.
Though Orenstein maintains that her books are always pure fiction, there are elements of her life sprinkled throughout them. “All of my books are set in places I’ve lived,” she explains. “And there’s one thing I love about fiction — everything happens, none of it is true. The feelings are true, but the actual events are made up.” Her stories also reflect her cultural identity — especially her experience as a culturally Jewish woman. “It’s not really a conscious decision,” she says. “It’s just like, this is the world I live in, so my characters live in it too.” For her, it’s about representation that feels real, subtle, and rooted in lived experience.
When we speak, Maine Characters is mere weeks away from hitting shelves, so Orenstein is focused on getting the word out about it. But when she’s actively writing or editing a book, it’s all about balance (because let’s not forget she’s *also* a full-time editor at a mahor media company). During the summer, she writes lakeside in Maine. “There are no friends, no restaurants, no workout classes,” she says. “So I just sit outside after work and write for about two hours.” The rest of the year back in Brooklyn, she swears by her “brunch shift,” a non-negotiable weekend writing block from 11 a.m. to 3 p.m. It might sound intense, but it works!
Looking back, Orenstein fondly remembers those early days when her career was just a twinkle in her eye. “When I landed my first internship interview, I was so nervous. I decided to listen to “Suddenly I See” by KT Tunstall because of The Devil Wears Prada, and it just became a tradition. Every time I went to an interview, I played that song,” she says. “When I landed the internship, I thought, ‘You’re on track. This is really happening.’”
And it still is.