Book Club Questions for In Five Years by Rebecca Serle

by Heather Caliendo
book club questions in five years - book club chat
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Book club questions for In Five Years by Rebecca Serle take a closer look at the relationships in this moving novel. For more context about the story, check out my spoiler-free review first.

When Type-A Manhattan lawyer Dannie Cohan is asked this question at the most important interview of her career, she has a meticulously crafted answer at the ready. Later, after nailing her interview and accepting her boyfriend’s marriage proposal, Dannie goes to sleep knowing she is right on track to achieve her five-year plan.

But when she wakes up, she’s suddenly in a different apartment, with a different ring on her finger, and beside a very different man. The television news is on in the background, and she can just make out the scrolling date. It’s the same night—December 15—but 2025, five years in the future.

After a very intense, shocking hour, Dannie wakes again, at the brink of midnight, back in 2020. She can’t shake what has happened. It certainly felt much more than merely a dream, but she isn’t the kind of person who believes in visions. That nonsense is only charming coming from free-spirited types, like her lifelong best friend, Bella. Determined to ignore the odd experience, she files it away in the back of her mind.

That is, until four-and-a-half years later, when by chance Dannie meets the very same man from her long-ago vision.

 Book Club Questions for In Five Years

  • The story starts off when Dannie does well in her job interview and she’s asked where she’ll see herself in five years. She answers the question easily not just because she practiced but rather she just “knows.” Let’s talk about Dannie’s confidence at the beginning of the story. Why do you think she was so sure of where her life would go?
  • While David does propose that night, when Dannie goes to sleep and wakes up—she’s in a different apartment with a man who is definitely not her fiancé. Let’s talk about Dannie’s “dream” in chapter 3. What did you think as you read it? Why do you think Dannie was so shaken by it?
  • Dannie is worried she’s seen a glimpse of her future where she’s no longer with David and she can’t handle not having a firm grasp on her future. Let’s talk about how Dannie became so worried about losing control yet everything in life appeared to be leading up to the dream.
  • When she talks to a therapist about the dream, her therapist says that “sometimes unexplainable things happen.” Do you agree with this? Have you ever had a dream like Dannie did?
  • Let’s talk about the friendship between Bella and Dannie, which is really the heart of the novel. Why did they make such a good match for friends? Let’s talk about their differences. What do you think are some of the key aspects of life that Dannie learned from Bella?
  • What did you think when Bella’s new boyfriend Aaron turned out to be the same man from Dannie’s dream?
  • David and Dannie are engaged for four and half years but didn’t make any plans to get married—until Dannie gets spooked by meeting Aaron. Why do you think, before that, that they never planned the wedding? Why weren’t they a good match in the end?
  • Bella and Aaron get closer, much to Dannie’s dismay. She becomes obsessed with worry that her dream will come true and she’ll betray Bella. But the story takes a different turn when they find out that Bella is actually suffering from ovarian cancer and it’s severe. Let’s discuss this and how it changes the story.
  • This story is billed as a love story but not in the way you would expect. It really is about the love between two friends. Let’s talk about this.
  • Dannie has experienced a lot of loss—first her brother as a teenager and then with Bella. Dannie says she’s always been waiting for tragedy to show up on her doorstep again. Let’s discuss this—is tragedy in some form or another inevitable?
  • Now let’s jump to chapter 41 when Dannie experiences the “dream” in real life. What are some of the key differences between the dream and reality? Do you think Aaron also experience the same dream like Dannie did?
  • After they sleep together, Dannie thinks: But it is not love, no. I mistook it. I mistook it because I did not know; I had not seen everything that would get us here. It is not love, this feeling. It is grief. Let’s discuss this—why do you think they felt this bond to come together in grief?
  • Despite trying everything in her power, the “dream” comes to fruition for Dannie, just not in the way she anticipated. Let’s discuss fate and the bigger message the author was trying to convey.
  • After Aaron leaves, Dannie runs into Bella’s doctor at the local deli where they seem to have a bit of a moment. What do you think happens next for Dannie?
  • What are some of the key takeaways of the novel for you?
  • If they make this novel into a movie or TV series, who should play the main roles?

What to Read Next

Hope you enjoyed book club questions for In Five Years! Here are some more contemporary fiction recommendations along with links to book club questions.

The Friend Zone by Abby Jimenez

The last story that got me as much emotionally as In Five Years did is definitely The Friend Zone by Abby Jimenez. The cover is cutesy but there’s so much going on in this novel. It has a bit more comedy but it’s also full of heart too. I highly recommend this one!

Kristen Peterson doesn’t do drama, will fight to the death for her friends, and has no room in her life for guys who just don’t get her. She’s also keeping a big secret: facing a medically necessary procedure that will make it impossible for her to have children.

Planning her best friend’s wedding is bittersweet for Kristen — especially when she meets the best man, Josh Copeland. He’s funny, sexy, never offended by her mile-wide streak of sarcasm, and always one chicken enchilada ahead of her hangry. Even her dog, Stuntman Mike, adores him. The only catch: Josh wants a big family someday. Kristen knows he’d be better off with someone else, but as their attraction grows, it’s harder and harder to keep him at arm’s length.

The Friend Zone will have you laughing one moment and grabbing for tissues the next as it tackles the realities of infertility and loss with wit, heart, and a lot of sass.

You can order the book on Amazon here. Check out my book club questions here.


The Dinner List by Rebecca Serle

If you haven’t read Rebecca’s previous novel, The Dinner List, go out and get a copy now! It’s another original story full of love and heartbreak. While In Five Years focuses more on friendship, The Dinner List centers on different relationships. It’s another fantastic one by her.

At one point or another, we’ve all been asked to name five people, living or dead, with whom we’d like to have dinner. Why do we choose the people we do? And what if that dinner was to actually happen? These are the questions Rebecca Serle contends with in her utterly captivating novel, The Dinner List, a story imbued with the same delightful magical realism as One Day, and the life-changing romance of Me Before You.

When Sabrina arrives at her thirtieth birthday dinner she finds at the table not just her best friend, but also three significant people from her past, and well, Audrey Hepburn. As the appetizers are served, wine poured, and dinner table conversation begins, it becomes clear that there’s a reason these six people have been gathered together.

You can order the book on Amazon here. Check out my book club questions here.

Happy reading!

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