Magazine’s matchmaker and ‘Gossip Girl’

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By Gianluca Russo
Campus News

“Living the dream” is an understatement when it comes to Hannah Orenstein. As previous Assistant Features Editor of and current Dating Editor of Elite Daily, she spends each day living out her high school fantasies, writing about teen life, pop culture, relationships, sex ed and more. But the real reason we can’t get enough of Orenstein isn’t because of her extremely successful career (okay, her career does play a HUGE part in our obsession), but due to the fact that she is, quite literally, the real-life Blair Waldorf.

That’s right: Blair Waldorf, Upper East Side queen of the CW’s hit show “Gossip Girl.” Like many millennial women and men, Orenstein quickly became a fan of the show when it premiered ten years ago. Soon enough, however, her love for Gossip Girl became an inspiration that would lead her to her dream job.

“I totally fell in love with it!” Orenstein tells Campus News via phone. “I started watching it religiously as many people my age did, but I think what was different about my connection to the show is that I wanted to see if it was real; I wanted to make it into a dream.”

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Following in Waldorf’s footsteps, Orenstein moved to New York City, attended New York University and interned at some of the largest publications in the industry, including the Huffington Post, Mashable, ELLE and During her senior year, an editor at Seventeen put a call out looking for personal essays. Determined to be published there before graduation, Orenstein came up with the perfect pitch: a piece entitled “I Based My Entire Life on ‘Gossip Girl’ and I Don’t Regret It.”

Upon publication on, the piece went viral. “I didn’t expect it, [my editor] didn’t expect it, but it got hundreds of thousands of views.”

Of course, Orenstein was well aware that certain parts of “Gossip Girl” were not exactly admirable, explaining, “Did I move here with the intention of becoming a teenage billionaire, drinking at hotel bars after school? No. For me, and I think for a lot of people, the show provided a life path when we weren’t sure who we really were or who we wanted to become. And the show said that it’s okay to want to move to a city and be glamorous and have this beautiful wardrobe. That’s why I connected with “Gossip Girl” and I think that’s why people still connect with it today.”

After Orenstein graduated from NYU in May of 2015, the editor at Seventeen encouraged Orenstein to apply for a weekend editor position. Yet, after submitting her application, life took an unexpected turn.

Photo by Elyssa Goodman

“That Monday, she said that a bunch of people called in sick and asked if I could please come in and fill in and write for them that day, and I did. Two days later, she offered me a position as a regular writer,” she recalls.

Orenstein worked at ever since then, making her way on up to Assistant Features Editor. The position is one she’s worked toward and dreamed about since she was 11 years old when she picked up her first copy of J-14. Recently, however, she made the switch over to Dating Editor at Elite Daily. But at night, Orenstein has been accomplishing a new goal she never thought she’d make: becoming a published author.

Orenstein’s first novel, “Playing with Matches,” is set to be released by Touchstone Books in June 2018. It is inspired by her short time as a matchmaker in college.

“My senior year of college, I took a creative writing class and I had to submit a short story. I chose to write about matchmaking, and the advice from the professor and other students was to keep going. So with that feedback, I started working on the first draft in May of 2015 when I graduated college.”

Orenstein had worked as an amateur matchmaker for about a year before working professionally with a New York City based company for seven months.

“I was 21 years old when I started working as a matchmaker, and I was setting up people who were in their 30s and 40s and 50s who were looking to me to find them love. It was a really intense experience and I learned a lot. There were a lot of really funny, sad and surprising moments along the way.”

“Playing with Matches” follows the life of 22-year-old Sasha Goldberg, a professional matchmaker in New York City. From trolling Tinder to coaching clients to dealing with heartbreak, the novel is sure to be a must-read. Orenstein is incredibly excited for the book to become available and hopes that audiences will devour and love each word and page.

“I love to connect with readers who care about the same types of stories that I do, and I hope to make this book something memorable.”

For more about Orenstein and to stay up-to-date with news about “Playing with Matches,” follow her on Twitter @HannahOrens or visit

Regular contributor Gianluca Russo is a freelance writer who attended Schenectady County Community College and now attends UAlbany.