This reading group guide for Cobble Hill includes an introduction, discussion questions, ideas for enhancing your book club, and a Q&A with author Cecily von Ziegesar. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.

Introduction

From the #1 New York Times bestselling author of the Gossip Girl series, an irresistibly entertaining novel chronicling a year in the life of four families in an upscale Brooklyn neighborhood as they seek purpose, community, and meaningful relationships—until one unforgettable night at a raucous neighborhood party knocks them to their senses.

Welcome to Cobble Hill.

In this eclectic Brooklyn neighborhood, private storms brew amongst four married couples and their children. There’s ex-groupie Mandy, so underwhelmed by motherhood and her current physical state that she fakes a debilitating disease to get the attention of her skateboarding, ex–indie musician husband, Stuart. There’s the unconventional new school nurse, Peaches, on whom Stuart has a drooling crush, and her disappointing husband, Greg, who wears noise-canceling headphones everywhere.

A few blocks away, Roy, a well-known, newly transplanted British novelist, has lost the thread of both his next novel and his marriage. His wife, Wendy, is not the corporate powerhouse she pretends to be. Around the corner, Tupper, the nervous designer of a ubiquitous surveillance device, struggles to pin down his elusive and terrifying artist wife, Elizabeth. Throw in two hormonal teenagers, a nine-year-old pyromaniac, and a drug dealer pretending to be a doctor, and you’ve got a combustible mix of egos, desires, and secrets bubbling in brownstone Brooklyn.

Witty and sharp, Cobble Hill is a novel about modern families with all their flaws and foibles, a coming-of-age story about grown-ups who feel anything but adult.

Topics & Questions for Discussion

1. There’s a large cast of characters in Cobble Hill, and von Ziegesar portrays both their good and not-so-good qualities. Which character do you find the most sympathetic, despite their flaws?

2. In the past few decades, Brooklyn has become an increasingly prevalent setting in pop culture; how does Cobble Hill compare to your ideas of Brooklyn from other books, movies, and TV shows? What do you think the author wanted to emphasize that other authors or screenwriters haven’t?

3. One big plot point in Cobble Hill is author Roy Clarke attempting to write his novel. Were you intrigued by its plot? Would you want to read the novel Clarke is working on? Do Clarke or his book remind you of any real-life writers?

4. Another creative Cobble Hill neighbor is Stuart, whose song lyrics are strewn throughout the novel—which were your favorite? How did they help you understand Stuart better as a character?

5. Cobble Hill is also concerned with the lives of its younger residents. Are teenagers Liam and Shy a good match for each other? How are their impressions of Cobble Hill different from those of the adult characters?

6. A very dramatic moment in the novel is when Liam and his friends—somewhat accidentally—set the local playground on fire. Do you think the punishment the boys received was fair, or do you think they got off easy?

7. Which of the four couples were you most fascinated by? Inside whose beautiful Brooklyn house would you most like to be a fly, or one of Tupper’s hidden cameras, on the wall?

8. All of the main characters get caught up in telling lies and keeping secrets from each other. Were you amused by their untruths or frustrated that the characters wouldn’t just talk to one another? Can you think of reasons why each character felt like they had to keep their secrets to themselves?

9. Although it’s in the middle of a big city, Cobble Hill has the feel of a small town. What techniques does the author use to make the neighborhood feel like its own confined place and not part of one of the largest cities on earth?

10. Were you surprised by the characters’ reaction to Mandy’s confession at the Bonfire Night party? Why do you think they were so accepting? If you were Mandy’s friend, would you have forgiven her in a similar manner?

11. Why do you think Stuart and Peaches are willing to engage in a flirtation despite being married to other people? What attracts them to each other?

12. Reread the lines from Walt Whitman at the beginning of the novel. What is their significance? How do they set the stage for the story to come?

13. Why do you think so many of the characters in this novel are fascinated by the murders reported in The Brookliner? What role did the murders play in the novel? How did they allow us to learn more about the main characters?

14. Why do you think Peaches is so interested in Elizabeth’s project and performance-art bar? What does “working” at the bar satisfy in Peaches? Why do you think Peaches and Elizabeth get along despite their very different personalities?

Enhance Your Book Club

1. With its glamorous families, trendy location, and year-in-a-life timeline, Cobble Hill seems perfect for a TV or movie adaptation. Who would you cast as the main characters? What challenges do you think a screenwriter would face in adapting the book into a script?

2. Pick another contemporary novel set in Brooklyn, such as Modern Lovers by Emma Straub or Friendship by Emily Gould, and discuss how the characters compare to those in Cobble Hill. Do you wish one of the characters in Cobble Hill could meet one of the characters from the other Brooklyn-based novel you read? How do you think their interaction would play out?

3. Organize a karaoke night with your book club, putting some of the songs from Cobble Hill on the playlist. Whether you want to call it performance art or not is up to you!

A Conversation with Cecily von Ziegesar

Q: You live in Cobble Hill. When and why did you decide you wanted to write a novel about your own neighborhood? Were you at all worried that your neighbors would think you were writing about them?

A: It’s very important to me that my books be set in a real place. The setting is as much a character in the story as the people themselves. But this is a work of fiction. I am very definitely not writing about my neighbors. The characters in Cobble Hill are my own creations. On the other hand, it’s also a love letter to, or at least a letter of admiration for, the neighborhood where my husband and I have raised our children and grown into middle age.

Q: Were there any classic New York novels or works of nonfiction that inspired you while writing Cobble Hill?

A: I try not to read anything even remotely like my own writing—any current fiction—when I’m writing. I did some reading about Mars. I reread Virginia Woolf’s Mrs. Dalloway. I read the books my teenagers had to read for school, because I like the idea of being able to talk to them about books (emphasis on the word idea). Edith Wharton’s The Age of Innocence and F. Scott Fitzgerald’s The Great Gatsby are the New York stories I read and reread. Richard Scarry’s What Do People Do All Day? is also a big one for me. It’s my favorite picture book. I never get tired of reading about Busytown. “Jason, the mason, made the foundation in the hole for the house to be built on.” That is probably my favorite line in literature.

Q: Did any of Roy’s struggles mirror your own during the writing process for Cobble Hill? What aspects of writing Cobble Hill came easily? What parts were more challenging? Did you ever want to start over and write a space opera set on Mars instead?

A: This is the first time I’ve written from the point of view of a writer and I don’t think I glamorize writing at all. It’s humiliating and frustrating and lonely and breeds insecurity. I think maybe Roy was my vehicle for addressing a lot of my own angst—is this terrible? What am I doing? But it was also fun showing through him how a writer’s mind—at least my mind—can go off in a million different directions. I still have no idea how I got Roy to Mars, but it made his struggle even more challenging, so I kept going.

Q: Why did you decide to have Mandy go to such extremes in her lie? Why did you ultimately decide to have her completely commit to this outrageous story?

A: Mandy is probably the most complicated person in the book. She’s selfish and smart and she knows she’s beautiful—she was a teen model. She’s wily. She’s restless, in a lazy way. She doesn’t quite know where to put her energy and craftiness, until she comes up with this crazy lie about having MS. I had a lot of fun with Mandy. The weird thing is I think she’s a good mom and a good neighbor. I mean, she’s learning to be a good mom and a good neighbor. She grows up quite a bit through the course of the book. Somehow, faking MS and staying in bed all the time brings her out of herself.

Q: Elizabeth and Tupper’s relationship is perhaps the least . . . conventional . . . of all the partnerships in portrayed in Cobble Hill. How did you come up with these two characters and their artistic pursuits? When did you decide to weave together the murders happening in the background and Elizabeth and Tupper’s artistic collaboration?

A: My husband works with artists, so I hear a lot about the art world. Artists tend to take themselves maybe a little too seriously. They’re fun to satirize. I liked the idea that there’s this news story of a murder that everyone is following and showing how it captivates their imaginations and sort of re-expresses itself through them. Tupper and Elizabeth are the only couple in the story without children. Elizabeth has a disparaging line early on about how in Cobble Hill the children are the art. She and Tupper are successful working artists, but their marriage is their greatest work of art.

Q: What do you love about your neighborhood? What details did you want to make sure to include in your portrayal of it in your novel?

A: In one scene Roy walks out of the neighborhood and then back again and immediately relaxes as the skyline lowers. That’s what it feels like to walk around here. The old butcher shop where I buy steaks for my son (I don’t eat meat) is pretty great. So is the little cinema. And I really can hear the Staten Island ferry’s horn.

Q: There are two events during which almost all the characters convene: the karaoke night and the Bonfire Night party. What did you want to accomplish in these two scenes? Which characters were you excited to have interact and which characters did you want to keep apart?

A: I like writing parties, jumping from point of view to point of view. I like bringing the reader to the party, showing what it feels like to want to be there, or to not want to be there—the awkwardness. A lot can be revealed about a person by the way they behave at a party.

Q: Almost every character is hiding a big secret. Were you ever anxious while writing the scenes when their secrets threatened to—or did, in fact—get out?

A: Everyone has secrets. They’re usually a bigger deal to the person keeping them than they are to anyone else. I think it’s more realistic when the big reveal isn’t so big after all. The people who care about us maybe know us better than we know ourselves. They are also the people we torment most.

Q: Why did you decide to also include the stories of the neighborhood teens and children? What was fun about including their perspectives? What did you find challenging?

A: The adults here are not very mature. The teenagers are pretty wise. I’m interested in the magical moment when we supposedly become adults. There are glimpses now and then, when one of the parents recognizes something in their kids or learns something from their kids. I think maybe that’s what it means to be an adult.

Q: Was there a character you especially enjoyed writing? Do you closely identify with that character, or are they so different from you that it made delving into their perspective a fun escape?

A: I felt very close to Roy, because he’s a writer, but I also felt close to Peaches. She’s sensitive and observant, cocky and insecure at the same time. She’s a frustrated creative person, someone who always thought she’d write, or play in a band. Instead, she’s a school nurse; she just has to come to terms with the fact that she actually likes it and is great at it. She’s also a great mom.

Stuart was probably the biggest escape. We have absolutely nothing in common. Writing his lyrics was fun. Giving him a skateboard was fun, too—there are a lot of grown men on skateboards these days.

I like the irony in the fact that all of my characters are dissatisfied. They live in one of the nicest neighborhoods in Brooklyn, but they aren’t smug; they’re still striving and stumbling. In a way, this book is about making things, or the effort one puts into to making them—art, books, music, marriages, families. There are a lot of parallels between writing books or making art or music and having children. You spend so much time hovering over them. Eventually you have to release them into the world. The best-case scenario is that they stand up on their own and surprise you by being kind of awesome.