Not many writers can say that their bestselling series gave rise not just to one hit television show, but two. When Cecily Von Ziegesar started writing the Gossip Girl series in the early 2000s, she expected her books to “fizzle and die on the shelf”—now, nearly two decades later, they’ve been adapted for television a second time over, coinciding with a splashy reissuing of the first three installments.
Though the Gossip Girl series became a New York Times bestseller when the third book hit shelves in 2003, Von Ziegesar credits the CW’s television adaptation, launched to great fanfare in 2007, with transforming her characters into household names. Now a cult classic, the show’s racy tales of sex, scandal, and heartache among the uber-privileged earned the devotion of teens and the outrage of parents, resulting in a bona fide cultural phenomenon. The books were banned in school libraries around the country; meanwhile, the show used the barbs of its critics, like “every parent’s nightmare” and “a very nasty piece of work,” as advertising fodder.
Now, Gossip Girl is poised to captivate another generation on HBOMax, where writer and showrunner Joshua Safran (an alum of the CW show) has rebooted the series, with a twist. Unlike the original series, which teased the identity of anonymous scandalmonger Gossip Girl until the very last episode, this show outs her to viewers right away, casting her as a group of teachers eager to clap back at their disrespectful students. Meanwhile, amid a cultural reckoning about privilege and income inequality, Gossip Girl 2.0 promises to interrogate its characters’ staggering wealth, rather than purely glamorize it.
Von Ziegesar wasn’t involved with the original Gossip Girl series, nor is she involved with the reboot, but all along, she’s been cheering on the shows (and catching the Easter eggs) from the sidelines. At HBO’s premiere party for the reboot, she was shocked to be greeted with reverence by the show’s young stars. “You're coming to talk to me?” she joked. That night, Von Ziegesar and her nineteen-year-old daughter went home with souvenir Constance Billard sweatshirts (by the way, we’ve been pronouncing it wrong all along; Von Ziegesar insists that the emphasis should be on the second syllable, not the first).
Post-Gossip Girl, Von Ziegesar branched out into adult novels. “Every time I write something, I want to write something really new, and not just do the same thing over and over again,” she tells Esquire. First up was Cum Laude, a novel about freshman girls at a Maine liberal arts college; then, she wrote Dark Horses, a psychological fiction about competitive riding inspired by her own background in the sport. Her latest is Cobble Hill, a wry, bittersweet novel about married couples and their children, set in her eclectic Brooklyn neighborhood. Cobble Hill, "a coming of middle-age" novel, marks a new direction for Von Ziegesar, a writer always looking to surprise herself.
Over oat milk lattes at Sant Ambroeus in Manhattan, Von Ziegesar remembered the ups and downs of the early Gossip Girl days, offered insight into the reboot, and dished on her new novel.
Esquire: Take me back to the beginning—when did you start writing Gossip Girl, and how did the series take shape over time?
Cecily Von Ziegesar: You're talking to a doddering old person now. I was 29 when I was writing it. When I finished, I was 30, and it went public when I was 31. I didn't have kids yet, and being in my twenties, I still had almost the same mindset I had in high school, so it really wasn't that much of a stretch for me to be writing the books. I had no trouble remembering what it was like, because I went to a small private school for girls on the Upper East Side. I fictionalized everything, but I based the character Dan on myself, and then I created these other characters based on people that I knew, mixing their personalities and names. The guys are all pretty much fictional, because I didn't really hang out with that many guys.
I was very much writing to entertain myself—to write a book that I didn't think existed yet. I really didn't think anyone was going to read it. I thought it was just going to fizzle and die on the shelf. I think that even the publisher, Little Brown, was a bit nervous about it, because it was racy and irreverent. They did a very small print run. The books didn’t become bestsellers until the third book came out. They came out every six months—the first in spring 2002, then the next in fall 2002, and then when the third was about to come out in spring 2003, it was on the bestseller list before it was actually on shelves. By then, I had an infant. Writing a book every six months was like churning out novels. It was crazy. Then I had another child, and I felt like a machine. On Christmas Day, I'd be like, "Hold on, I'll open presents when I’m done writing.”
It took over my life, but in a good way. When I heard the news that it would become a show in the early 2000s, my first reaction was fear. I thought, “I hope it’s good. Please make it not be terrible!” I was on set when they were filming the pilot. The cast was wonderful and it all looked really good, but I still hadn't seen the final thing. I was really, really thrilled with it. I remember writing the last few lines of the first book and thinking, “This is good.” I had a similar feeling after watching the pilot of the show. It became beyond anything I ever could have imagined.
I wasn't involved in the writing of the show. But it was still my characters, and they would give the books little nods that I felt like only I understood. I just met Josh Safran at the premiere party for HBO’s Gossip Girl; I hadn't met him before. He told me, "We used to all used to pass your books around in the writers room and use little snippets." I made a cameo in one of the episodes, and there was always fun little stuff going on behind the scenes. I used to Tweet during the episodes, but then somebody hacked into my Twitter and took over—one of the fans.
ESQ: That’s a plot straight out of Gossip Girl.
CVZ: She was pretending to be me. Eventually I got my Twitter back, but funnily enough, I'm not really a big social media person. It’s just not really my thing. I got my Twitter back and got verified by Warner. They were so apologetic that this had happened, and then I never used it. Then I was talking to my nephew and he said, "You're verified—that's so cool." I was like "Is it? Do you want to use it?"
Esquire: Did you ever expect Gossip Girl to get this big?
CVZ: Not at all. Actually, I feel like the books were never that big—it was all the show. I never expected Gossip Girl or the names Serena, Blair, Nate, and Chuck to become household names that everybody would be talking about. It was crazy.
ESQ: How do you feel New York City has changed since you first started writing the books?
CVZ: Gossip Girl is very much of this specific place. It's almost like a time capsule. When I was writing them, I didn't feel like the Upper East Side had changed very much since I’d gone to school there. I've actually never lived on the Upper East Side; I grew up on the Upper West Side, and now I'm in Brooklyn. But now, the Upper East Side has drastically changed. That was what was so nice about people who did live on the Upper East Side. When the show came out, people recognized icons of the Upper East Side, like the 75-year-old woman dressed head-to-toe in Chanel. I feel like now is a very specific time or everything has changed, but I don't think you could say that about the time that I was writing the books, or the time of the first show. I think that's something about this current iteration of Gossip Girl—they were very much aware of that. The entire city has changed. The entire world.
ESQ: It seems they’ve written that into the new show—the students are all excited to return to school after a year in lockdown.
CVZ: That was a surprise to me. I thought it was brave to do that, because I think a lot of people want to brush the pandemic aside and say, "Well, that never happened." But if you're a younger person, it’s a huge portion of your life. My son is 16. He just spent more than a year of his life going to Zoom school. That’s huge.
ESQ: The Gossip Girl books were frequently banned or challenged in school libraries. What was it like to be at the center of such a hotly contested debate?
CVZ: I actually thought it was really exciting to be on the banned books list, because Gossip Girl was right up there with books like The Catcher in the Rye and To Kill a Mockingbird. These books are so valuable. When I heard it was banned, I was like, “Alright, that’s great news.” They wouldn’t carry my books in Walmart stores or in the Bible Belt. But as soon as anything becomes contraband, teenagers become interested. That was fine with me. The National Coalition on Censorship ended up reaching out to me and I did a bunch of stuff with them, because I think they're a very cool organization.
ESQ: In addition to the HBO reboot, the first three Gossip Girl books have been reissued. What’s so enduring about these stories that they’ve been rediscovered for a new generation?
CVZ: I hope they don't feel too dated. I know there's a PalmPilot in one of them—nobody knows what a PalmPilot is anymore. Gossip Girl had her column; the word “blog” didn't exist. Even that’s already gone. When I was writing, I was aware that I wanted the books to be lasting. This was before social media, but it was basically the beginning of that. How does everybody know everything about everything? That's a very recognizable feeling, these days. Through Gossip Girl, every single character in the books instantly knows—or thinks they know—what's going on, what the gossip is, or what people are saying about somebody. It turns out that's what’s happened with all of social media. But what I hope I’ve done well in these books is bring you inside of characters who seem totally unapproachable—people who seem to be so privileged and gorgeous and untouchable. I think I make them feel very much human. That was my intention, anyway.
ESQ: How is it different to be a young person in 2021, as opposed to what it was like for Blair and Serena to be young in the early 2000s?
CVZ: I've been thinking about this, because I do have teenagers and I like to observe them. I've been paying attention to what they'll say. They don't correct me, or tell me what I can and can’t say. Their generation is more sympathetic. I think there's a difference between the people who are in their twenties and thirties now, and the ones who really are teenagers now. I think real teenagers now are really nice. That’s how I felt at the HBO premiere party, when I met the new cast members. I was just like, “You're coming to talk to me?” I feel like they're a little more open. They've also been exposed to a lot in a short amount of time. They’ve had to grow up quickly and be resilient.
For my generation, it was funny to be bitchy. This younger generation doesn’t necessarily find that funny at all. I appreciate that about them. But I like irony, and I have this terrible fear that everyone's losing their sense of irony. Maybe it dates me, but I’m not losing that.
ESQ: Much ink has been spilled about how Gossip Girl 2.0 intends to question the characters’ staggering privilege. How do you feel about that change?
CVZ: That feels very familiar to me, just going to school where I did and being a sensitive person. I don't think that's necessarily of the current moment; it also has to do with personality. Blair, Serena, and Nate didn’t give a shit. In this day and age, you can have somebody who doesn't give a shit, but you have to have contrast. I think it makes a lot of sense. You want to have sympathetic characters, and it’s an interesting comment on the times.
ESQ: The other big change with the reboot is exposing Gossip Girl’s identity right out of the gate, rather than teasing the mystery throughout the entire series. What do you think of that?
CVZ: Exposing her identity for the viewer, but not for the students, is a really interesting tactic. The teacher plot is fun and would never have occurred to me. In the books, the adults are largely absent. Nate's parents were always described as in Europe or at the opera. Rufus Humphrey was the only present parent. The teachers being second class citizens of the school is so accurate. Even in my time, in the eighties, that was accurate. It never occurred to me what the teachers thought of us. It’s so funny to show that perspective.
ESQ: Your latest novel is Cobble Hill. Where did that book begin for you?
CVZ: I’ve been gathering string on this idea for ages, because I was writing notes and collecting chapters over the course of four or five years. I kept starting and stopping the book. I had mom friends who said, “You should write the bitchy mom book.” I was like, “Absolutely not—I’m not going to write that.” That’s like Gossip Girl in Brooklyn, but not. Every time I write something, I want to write something really new, and not just do the same thing over and over again.
The book became more and more about writing itself, because it was hard for me to even get it done. We see Roy’s struggle with writing a book; that was my struggle with writing this book. I got really angry with myself. What's your problem? Just do it!When my in-laws came to visit from England, I joined the Brooklyn Writers Space, because I didn't want them to see me at home doing laundry instead of doing work. After that, I hammered out a first draft in two months. It was sitting in my head all along; I just needed to make myself sit down and write it. I came home one day and we were sitting around the dinner table. My son, who knew I’d been writing a book called Cobble Hill for years, said, "How's Cobble Hill?" I said, "I finished it.” He said, "Yeah, right.” I said, "No, I really did.”
I wrote Cobble Hill like I did Gossip Girl, in some ways. I was trying to borrow from my experience raising my kids in Cobble Hill and living there, but also having these weird fantasies. Meal kit boxes would arrive in our building and I’d think, “Whose are these? Why are they sitting here forever? I'm going to take them.” I never did, but… what's in there? I had a lot of fun creating what was in the food boxes that Mandy steals.
I feel like every thought that I ever had for five years has all gone into the book. But the main thing for me was writing a book that’s entertaining and funny and that you can read in one sitting if you want to. That’s what I think I’m meant to do—not to write a ponderous novel. Even though it took me forever to write the book, it shouldn't take forever to read it. It should be just as entertaining as streaming a great TV show. It's very much a middle-aged book, which takes people by surprise, because I'm supposed to be eternally Gossip Girl-age. But for me, it was very much a coming-of-age—a coming of middle-age.
ESQ: It’s such a contrast to Gossip Girl in that so much of the book is people going to school, picking up from school, hanging out, and cooking dinner. It’s a real departure from the constant cycle of parties and events in Gossip Girl. I loved the quiet domesticity of it.
CVZ: Well, that's kind of that's my life. Whenever people ask me about how to become a writer, I say, “You have to be willing to not do very much.” You’re alone in your house with yourself most of the day. Roy’s day consists of making toast and staring at the computer screen.
ESQ: Roy spends so much time worrying about how to live up to the blockbuster series he wrote. Is that an anxiety you have, or a pressure you feel?
CVZ: He’s much more conscious of it than I am, but I always have the sense that everybody else has some sort of expectation of what I will write or should write. I want my writing to happily surprise them. I want to produce something that nobody expected rather than churn out something that feels like a kind of imitation of something else. I couldn’t write Gossip Girl now, but I couldn't have written Cobble Hill then. I always want to push myself. That said, Roy’s struggle is my struggle.
ESQ: How do you feel you’ve progressed or changed as a writer, from Gossip Girl to Cobble Hill?
CVZ: I don’t know if I’ve actually progressed. I wish I was as productive as I was in my Gossip Girl days. I wish I was as fast. I didn’t have any expectations and there wasn’t any pressure to produce something wonderful. I didn't think anyone was going to read them. I was completely carefree. I didn’t think; I just wrote. I wish I could do that now.
Back then, I had a team of editors. I had to submit outlines and plots. I didn't actually follow any of the outlines; I hated outlining. I would write one out and submit it, then doing something completely different. But it was nice to know that people were waiting for what I was writing, whereas now, it's like writing into a void. But I do think Cobble Hill has more depth. There’s a lot going on in their lives. I have a different worldview than I once did. Perhaps ultimately, my experience hasn’t been for naught.
ESQ: Are you working on another novel?
CVZ: I started writing something and then put it to the side. There’s a line in Cobble Hill where Roy describes writing as like a dusting—it’s like snow piling up on cars. I've been trying to be patient with myself. I'm hoping that sooner, rather than later, the same thing will happen, where suddenly it'll all come out in a big rush. But for some reason, I need to keep stewing on it.
Most days, I go running. I'm thinking while I'm running. I can't listen to music or anything when I'm running, because that's when it's all the thinking gets done. That’s always been true. I’d be running or taking a shower; then I’d have a breakthrough, and I'd run to the computer. That’s the most fun for me, as a writer. The whole book is in your head and the whole path lies ahead. That was the fun of writing a series. It's like the whole cast of characters is alive in my head. I just have to figure out what’s going to happen to them next.
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Cecily Von Ziegesar on 'Gossip Girl' 2.0, What's Changed Since the Book, and Her New Novel - Esquire.com
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