This reading group guide for In Five Years includes an introduction, discussion questions, ideas for enhancing your book club, and a Q&A with author Rebecca Serle. 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

In Five Years is a striking, moving love story about Dannie Kohan, a high-powered corporate lawyer who has everything planned out. The story opens on the day she interviews for her dream job, nails it, and gets engaged to her longtime boyfriend—all according to her five-year plan. That night, when she and her new fiancé get home, she falls asleep on the couch. But when she wakes up, she’s suddenly in a different apartment, with a different ring on her finger, in bed beside a very different man. She looks over at the muted TV playing the news and sees the date: it’s 2025, five years in the future.

After a very confusing hour, Dannie wakes up again back in her normal life. She tries to shake the dream—or was it premonition?—by busying herself in work. She tells no one about it, not even her best friend, Bella. Then one day, four and a half years later, she comes face-to-face with the man from her dream. This stunning, heartbreaking story will leave you thinking about the unpredictable nature of destiny and make you want to call your best friend immediately.

Topics & Questions for Discussion

1. From the very beginning of the book, we learn that Dannie has rules and plans laid out for everything in her life. Do you believe this helps or hinders her? How does her philosophy regarding keeping everything in its place change over the course of the novel?

2. To Dannie, the law is “like poetry, but poetry with outcome, poetry with concrete meaning—with actionable power” (page 10). Later she describes the law by saying that “everything is there in black and white” (page 142). How does the law empower Dannie? To what extent do you think the law shapes how rigidly she sees the world? As the book goes on, power is often taken out of Dannie’s hands. Do you think her background makes this lack of control harder for her than it might be for others?

3. While Bella is a tragic character, she is not painted simply in an angelic light. Early on in the story, Dannie describes her as being “spoiled, mercurial, and more than a little bit magical” (page 6). Is Bella’s portrayal as a complicated, sometimes flawed character unique given the ending of the book and the typical depiction of the tragic heroine?

4. The scene between Dannie and Aaron in Chapter 3 is mirrored by the same scene in Chapter 41. How did your impressions of the two characters change over the course of the book? Why do you think the author chose to frame the story with two identical scenes that will mean different things to the reader at different points in the story?

5. Bella gifts Dannie a print by the artist Allen Grubesic that reads: I WAS YOUNG I NEEDED THE MONEY. All the characters in the book are well-off financially by the time we meet them. What do you think the print’s message means in the context of the story?

6. Dannie believes that “Bella lives in a world I do not understand, populated by phrases and philosophies that apply only to people like her. People, maybe, who do not yet know tragedy” (pages 44–45). How do you think the death of Dannie’s brother at such a young age affects her outlook? Do you think she envies Bella for not carrying a similar burden, or does she look up to her for it? How do you think the fact that Dannie has already lost someone close to her affects her when Bella’s diagnosis is revealed?

7. Bella introduces her new boyfriend as Greg, but, of course, Dannie already knows him as Aaron and has a hard time referring to him as anything other than Aaron. Why do you think he is introduced to us with two different names? Is Bella’s version of him different from Dannie’s version of him?

8. Dannie visits a therapist, Dr. Christine, once after her dream and once after she meets Aaron in real life. Why do you think she sees Dr. Christine only twice? What decisions does Dannie make after leaving these appointments?

9. How does Dannie and Bella’s relationship change after Bella’s diagnosis? How does it affect the other relationships in Dannie’s and Bella’s lives? Why do you think it’s easier for Bella to be around Aaron than it is for her to be around Dannie?

10. Were you surprised that Dannie and Aaron kissed when he reveals that the apartment is a gift from Bella? Do you think it amounts to a betrayal of Bella’s trust? How does Dannie and Aaron’s connection to Bella intensify their own relationship?

11. Fate is a concept that is played with often throughout the novel. Dannie fights to change the fate she saw laid out in her vision. Aaron told Bella he was fated to end up with her. How do fate and free will interact in the novel? Do you think the book comes down on the side of one over the other?

12. Near the end of the book, Bella tells Dannie that she is meant to have love beyond her wildest dreams because “that’s the way you love me” (page 205). How does the book portray the roles of romantic and platonic love? How did the book subvert the idea that the great love of Dannie’s life would be one of the two men we were introduced to at the beginning of the novel?

13. Were you surprised that Dannie and Aaron did not end up together? What do you think this means for Dannie’s journey and her future relationships?

14. Magical realism is an element of the story but only when it comes to Dannie’s ability to see one evening five years in her future. Why do you think there’s a magical component in this one instance but nowhere else? Did the book’s hyperrealistic premise affect your expectations for how it would end?

Enhance Your Book Club

1. Iconic New York City locations, restaurants, and shops are mentioned throughout the novel. Next time you visit New York City, take a walking tour to some of them, including the Rainbow Room, Buvette, Bryant Park, and Rubirosa. Find a full guide in the illustrated reading group guide on the author’s website, rebeccaserle.com.

2. In Five Years often plays with preconceptions and blind spots when it comes to fate, love, and friendship. Consider your own opinions on the themes discussed in the book: Do you believe in fate over free will? Are any of the strongest relationships in your own life with someone other than a romantic partner? Where do you see yourself in five years, and how fixed is that vision of the future?

3. Read The Dinner List with your book club (if you haven’t already!) and compare how the roles of love, friendship, and magical realism come into play in both of Rebecca Serle’s recent novels.

A Conversation with Rebecca Serle

Q: In Five Years and The Dinner List both take place in New York City, and the city is a central feature of both novels. How did you create such a sense of place for your books? Is the NYC of The Dinner List different from the one in In Five Years? Will you continue to write novels based in NYC, or will they be set elsewhere?

A: I have been in love with New York City since I was a little girl—Manhattan has always been almost a person to me. It’s romantic, mercurial, and specific. The city is also the ideal place to set a book because it’s so full of connection—street corners, cramped apartments, and subway cars. It’s so easy to smack up against someone else’s humanity there. Sabrina’s New York in The Dinner List is less privileged than Dannie’s and probably mirrors my early years in the city better. Both novels have lots of my old haunts, though! You’ll find my favorite restaurants, coffee shops, and bars where I, too, have experienced heartbreak on every page. I lived it before I ever wrote about it, and I hope that comes through in my work.

I moved to Los Angeles this year, and my new novel takes place, in part, in California. I could see setting subsequent work in my new (very sunny) home.

Q: Dannie and Bella are such distinct characters. Why did you choose to portray them so differently? Do you think they help balance each other out? Who do you think you have more in common with, the pragmatic, by-the-numbers Dannie or the artistic, free-spirited Bella?

A: I knew that in order for the conceit to work, Dannie would have to be someone with an airtight life plan. She would have to know exactly what she wanted and was building toward. Dannie comes by her uptight nature honestly. She lost her brother when she was young and has had the need to control her life since, to make sure she is never struck down by tragedy again. I also knew I wanted to give her a counterpoint in Bella. Bella does not have any of Dannie’s rules about life—she is open, creative, and impulsive. In many ways, Dannie’s journey over the course of the novel is to embrace her own Bella-ness. I think I’m a pretty clear mix of the two, but, gun to my head, I’d say I’m more like Dannie.

Q: Is the relationship between Dannie and Bella reminiscent of any of the friendships in your own life?

A: The female friendships in my life are of paramount importance. They are my great loves. I think in some relationships I’m the Dannie and in some I’m the Bella. I turn to my friends for everything, like relationship advice and work input. I moved across the country this year and could never have done it without their support. I feel extraordinarily lucky to have them.

Q: The novel spans five years. How did you choose what to show us and what to summarize?

A: The plot doesn’t really accelerate in a significant way until Dannie meets Aaron again. So I knew that what happened in the years between, while maybe being interesting for Dannie’s life, would not be particularly interesting for the purposes of our story. From there, I needed about six months to tell the story I wanted to tell, and to earn the emotional arc.

Q: Why did you decide to have Dannie be a lawyer? What research into law did you do in order to write about her career? Was it important to you to portray your two female lead characters as having high-powered, successful careers?

A: I am lucky enough to have a lot of super successful women in my life, some of whom are corporate lawyers. I turned to them for advice, and also did research into the firm where Dannie works. Before Dannie, I had never written a character who was so unapologetic about her desire for financial success. I found her voice very satisfying—and surprising!—to write. I love that about her, and a lot of her ambitions mirror my own.

Q: Neither Dannie nor Bella is particularly close with her parents, and there is an emphasis on chosen family—especially when it comes to their lifelong relationship with each other. Are these kinds of essential friendships something you’ve explored in your past novels? How is chosen family important in your own life?

A: I’m my parents’ only child, and I think, as any only child knows, you need your friends to be like family. My girlfriends are my sisters, and they show up for me the way any blood relative would. I wanted to give Dannie and Bella that tie. Bella has been the great love of Dannie’s life. I relate to that level of loyalty and heart connection. I believe very strongly in chosen family.

Q: Speak to your exploration of fate versus free will in your novel. Did you know from the beginning that Dannie’s premonition would come to pass?

A: All of my novels since my very first book, When You Were Mine, are about the dialogue between choice and destiny. To me the most interesting question of our human existence is: “How much is in our control, and how much is going to happen regardless of what we do?” I knew that Dannie would live that hour and it would be exactly the same as the hour she lives at the beginning of the book, meaning all of the same things would happen. But I also knew it would mean something entirely different than what she’d been anticipating. That, to me, is really the thesis of the novel: we can think we know what is coming, but we can never know what it will mean.

Q: The book is framed as a love story, with two love interests that Dannie must choose between. How did you want to subvert the traditional love story narrative? Do you think readers will expect the change that happens midway through the book?

A: I’m not sure! But I can say I’m far more interested in writing about the complicated dynamics between women than I am about traditional romantic notions of love between a man and a woman. I love a good love story, but my books tend to feature female friendships front and center. I still think the most important relationship in The Dinner List is the one Sabrina has with Jessica, even though her love story with Tobias takes up more page space. Bella is the most important relationship in Dannie’s life, and I think that becomes clearer as the book goes on. That’s not to say David and Aaron are unimportant—they are extremely important. They’re just not as important as Bella.

Q: Was it challenging to write about Bella’s diagnosis and subsequent struggle with cancer? What research into ovarian cancer did you do in order to portray it?

A: It was extremely challenging, and I almost didn’t do it. For a while I tried to figure out a way for Bella not to have to get cancer, but I couldn’t come up with anything that would be as powerful or turn Dannie’s life upside down in the same way. Once I committed, I told my friend and fellow author Leila Sales how scared I was to write this. She told me to just stay close to Dannie, to write beside her, and to remind her that I was there. I still tear up thinking about that advice. It’s a writing philosophy I’m bringing to all my subsequent work.

For research, I spoke to doctors, visited the hospital, and researched both Bella’s diagnosis and subsequent treatment as best I could. I do not pretend to be a medical expert, and this book remains a work of fiction.

Q: Do you have any favorite books or movies that inspired you as you were writing In Five Years?

A: The novel opens with a quote from Nora Ephron. Her work in both film and books was hugely influential to me as a storyteller. In fact, she is one of the five people on my dinner list! I love any good New York love story. Someone Great, a film by Jennifer Kaytin Robinson, was a must-see of last year. The Modern Love column, as well. I’ve read it weekly for fifteen years.

Q: Why did you choose to use magical realism in the premises of both In Five Years and The Dinner List? What do these magical elements allow you to explore that you would not be able to otherwise?

A: The magical element allows for the conceit to be more magnified. The magic in my novels is never particularly overarching. It’s really just the one thing that injects into the narrative in a way that allows for expansion. For The Dinner List, it’s the dinner table, obviously. But I think as time goes on we begin to forget the impossibility of this meal, and simply start focusing on the relationships that are unfolding. Similarly in In Five Years, the magic is the flash forward. It’s key to the plot, of course, but as Dannie integrates the experience into her life, so do we. It’s simply a tool for us to get where we need to go.

Q: The premise of The Dinner List is based on the question “If you could have dinner with any five people, alive or dead, who would it be?” In Five Years is based on the question “Where do you see yourself in five years?” What attracted you to the idea of recasting these casual conversation starters as the jumping off point for your recent novels?

A: The Dinner List took a long time to write, and in between when I began it and when I came back to finish it, my grandmother passed away. What was once a fun, zany conceit became very personal: What wouldn’t we give to have one last dinner with a person we love whom we’ve lost? The book grew out of my desire to explore that idea. For In Five Years, the question came closely with the conceit. I knew I wanted to explore the idea of seeing a future that looks very different from the one we are planning. I am also fascinated by scientific data that is suggesting that the future in fact influences the present. Perhaps the choices we are making are not building a moldable future, but are informed by one that has already solidified. It’s intriguing stuff!