Intergenerational Novels: Books that Connect Generations
When we came up with the idea for our Lifetime of Reading Challenge, our primary goal was to encourage our readers to explore novels that highlight the joys and challenges of each phase of life. Throughout this reading challenge, we’ve seen the world through the eyes of characters of all different ages. Now, we’re excited to read about relationships between characters of different generations, emphasizing books about intergenerational friendships.

In selecting titles for our list, we’ve focused primarily (but not exclusively) on contemporary stories that feature intergenerational friendships between characters that are more than a few decades apart in age. We’ve curated a diverse list of recommended books, ranging from literary fiction to lighter reads. In addition to reflecting a wide range of life experiences, the main characters also vary in ethnicity, religion, sexual orientation, class, background, lifestyle, and more.
Books with Intergenerational Friendships
How to Age Disgracefully
Book Summary
When Lydia takes a part-time job running the local senior center three afternoons a week, she has no idea what she’s getting herself into. In addition to a more rambunctious group of seniors than she expected, the council is trying to sell the building that houses both the senior center and a daycare center.
Daphne has been reclusive for decades, hiding from a mysterious past that may still be trying to catch up to her. But, her 70th birthday prompts reflection on her life. She decides that MAYBE it wouldn’t be terrible to find a friend…or even a boyfriend.
What Daphne finds at the senior center is not what she expects. Despite her initial reservations, an unlikely chain of new relationships (including a teenage father, a dog, and some grumpy old men) changes her life in every way.
The Book Girls Say…
Melissa rated this enjoyable story five stars. She loves a strong older character, and when lonely people of different generations connect to form a new family, this novel does that well. It’s both heart-warming and funny, which is the best combination!
The Authenticity Project by the same author is another great novel for this prompt!
Also Featured on These Book Lists:

Great Big Beautiful Life
Book Summary
Margaret Ives is the daughter of one of the most storied (and scandalous) families of the 20th century, but the former tabloid princess hasn’t been seen in years. Now in her 80s, this tragic heiress is ready to tell her story. She invites two authors to Little Crescent Island for a one-month trial period, after which she intends to choose one to write her memoir.
The two authors she has invited couldn’t be more different. Hayden Anderson is a Pulitzer-Prize winner with the personality of a thundercloud. Alice Scott, on the other hand, is an eternal optimist still working toward her big break as a writer.
Margaret is only giving each of them pieces of her story, but because of their ironclad NDAs, Hayden and Alice can’t share what they’ve learned in order to put together a more complete picture. Whether her story is a mystery, a tragedy, or a love ballad is yet to be determined. The same can be said for the story between Alice and Hayden, who can’t deny the inconvenient pull between them each time they’re in the same room.
The Book Girls Say…
We’ve always loved that Henry’s romance novels are more than just that, but the consensus seems to be that Henry has entered new writing territory with this novel. Early readers say that this book’s writing style is classic Emily Henry, but it’s even heavier on the plot and lighter on the romance (with many comparing it to the work of Taylor Jenkins Reid).
Also Featured on These Book Lists:
Calling Me Home
Book Summary
Eighty-nine-year-old Isabelle needs a big favor. She needs a ride from Texas to Cincinnati, Ohio, to attend a funeral… tomorrow. She asks her hairdresser, Dorrie, to drop everything to take her there, but she gives few details as to why it’s so important she be there. Over the years, Dorrie, a 35-year-old Black single mom, has developed a friendship with Isabelle and agrees to drive the elderly woman across the country.
Dorrie has a lot on her mind between the new man in her life and her teenage son’s irresponsible decisions. But she’s also curious about Isabelle’s guarded past and hopes that along the way, she may be able to unlock some of her friend’s secrets. And she does…
Isabelle confesses that as a teen in 1930s Kentucky, she fell madly in love with a would-be doctor and the son of her family’s Black housekeeper. In the sundown town, where African Americans weren’t allowed after dark, theirs was a forbidden relationship with tragic consequences.
The Book Girls Say…
This highly-rated debut novel is described as a very emotional read, so keep the tissues handy.
Tell Me How This Ends
Book Summary
Thirty-two-year-old Henrietta once wanted to be a librarian, but now her work transcribing life stories for terminally ill patients is the perfect distraction from her past. She’s usually good at separating fact from emotion, but when Henrietta meets 60-something Annie, who is both eccentric and terminally ill, she feels herself being drawn into Annie’s story.
When Annie reveals her sister’s mysterious drowning back in 1974, Henrietta begins methodically following the story’s loose ends. Annie, on the other hand, has long been afraid to look too closely into her murky memories of that terrible night. The push and pull between these two women will unearth a surprising emotional connection between them before it’s too late.
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Eddie Winston Is Looking for Love
Book Summary
Eddie is 90 years old, and while he has lived a good life, he has never been kissed. Despite this, he remains a romantic at heart. He spends his days volunteering at a charity shop in his town of Birmingham, England, where he sorts through donations. He’s always careful to preserve letters and tokens of love that others may toss aside as not valuable.
At the shop, he meets 24-year-old Bella, who has just lost the love of her life. When Bella learns that Eddie is still waiting for his first kiss, it’s the perfect distraction from her own troubles. She resolves to help him find love, sparking an adventure that will take them to unexpected places. Their intergenerational friendship will make you wish the endearing Eddie were a real friend in your own life.
The Book Girls Say…
Eddie Winston Is Looking for Love is said to be an uplifting, funny, and powerful story of friendship and finding love in an unexpected place.
Author Marianne Cronin also wrote the much-loved novel The One Hundred Years of Lenni and Margot, which would also be a great choice for this prompt!
Also Featured on These Book Lists:
Have You Seen Luis Velez?
Book Girls’ Readers Rate This Book
100% Would Recommend to a Friend
Book Summary
Raymond is a shy Black teen who feels like he doesn’t fit in anywhere – not with his complicated family and not at school. Mildred is a blind 92-year-old Holocaust survivor living alone since her caretaker disappeared. When Raymond meets Mildred in his apartment building, she introduces herself with the question: “Have you seen Luis Velez?”
Raymond begins to help Mildred with her weekly errands to the banks and the grocery store, and also hopes to help her track down Luis. In a short time, they’ve formed an unlikely friendship. Raymond demonstrates that for every terrible act, there’s a mirror image of kindness. And Mildred helps Raymond see that even when life is difficult, there is always hope.
The Book Girls Say…
This heartwarming story will overwhelm you with the kindness of the characters, give you new hope for humanity, and encourage you to be your best.
Each page is a sweet testament to the rewards that can come when you take time for others – whether that be opening your door to their questions, or simply walking them to the grocery store. The book balances these positive moments with struggles and very hard times for different characters. Melissa finished the book quickly because after every chapter, you can’t wait to find out what happens next.
If you’ve already read and enjoyed this novel, we also recommend Allie and Bea by the same author for this prompt!
Also Featured on These Book Lists:
Literary Fiction
Remarkably Bright Creatures
Book Girls’ Readers Rate This Book
98% Would Recommend to a Friend
Book Summary
In this charming debut novel, seventy-year-old Widower Tova works at the Sowell Bay Aquarium to occupy her mind and time. She takes pride in cleaning perfectly every night, even though she doesn’t need the money. She loves all the aquarium life but forms a special bond with the intelligent (and curmudgeonly) octopus named Marcellus.
He’s just as surprised to feel friendly toward this human who visits him nightly. Soon, he connects the sadness he sees in her with something he saw in the ocean long ago. Can he help her solve the mystery of her son’s disappearance 30 years ago?
The story is told from three alternating viewpoints – those of Tova and Marcellus, as well as Cameron. Cameron is an aimless 30-year-old who was abandoned by his mother when he was just a child. His aunt did her best to raise him, but his life has been a series of dead-end jobs. He travels to Sowell Bay in search of answers that may give his life direction. He winds up taking a temporary position at the aquarium.
The Book Girls Say…
Marcellus stole our hearts, but we also loved the human characters and their struggles in different phases of life. Young or older, so many people deal with loneliness and loss. Watching characters process and evolve through that was a heartwarming treat.
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24 Engaging Full Cast Audiobooks
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PS: We also have a printable Remarkably Bright Creatures book club guide available on Etsy, including discussion questions, themed games, a Marcellus bookmark, and more!
West With Giraffes
Book Girls’ Readers Rate This Book
96% Would Recommend to a Friend
Book Summary
West With Giraffes is a charming tale of adventure that takes you on the ride of a lifetime from the East Coast of the US to the West, alongside a rowdy 17-year-old, a grumpy older man, and two giraffes. The year is 1938, and no American zoo has successfully housed giraffes before. The female zoo director of the San Diego Zoo believes she can do it. The giraffes have just survived a hurricane en route to the East Coast, and Riley Jones, the curmudgeonly head zookeeper, is responsible for safely transporting the giraffes from New York City to San Diego.
America is still in the throes of the Great Depression, and the Dust Bowl conditions continue to ravage the drought-stricken Southern Plains states. Jones begrudgingly teams up with a starving teenager named Woody to help him make the coast-to-coast journey. The adventures along the way include run-ins with circus con artists, being tailed by a female photographer looking for a big scoop, an emotional visit to Woody’s hometown, and so much more.
The Book Girls Say…
At its heart (and this book is filled with LOTS of heart), this is Woody’s coming-of-age story in which Riley Jones takes on the role of a father figure/mentor. Now, at the age of 105, Woody recounts his 12-day cross-country trip with Jones and the giraffes and how it shaped his life.
In writing this historical fiction novel, author Lynda Rutledge started with the true story of two giraffes being transported cross-country in the 1930s and then imagined what that road trip might have been like. She includes real newspaper clippings throughout the book to indicate to readers the parts of the story that are based on actual facts.
Also Featured on These Book Lists:
Books About Traveling Across America
Books Set in the 1930s
Unforgettable Dust Bowl Books
Readers’ Favorite Books: 2023 Edition
PS: We also have a printable West with Giraffes book club guide available on Etsy, including discussion questions, bonus giraffe content, custom bookmarks, and more!
The Heirloom Garden
Book Girls’ Readers Rate This Book
100% Would Recommend to a Friend
Book Summary
After losing her husband in WWII and her daughter to illness, Iris walled herself off from the world. She’s spent many decades hiding behind the tall fence around her home. In place of human connection, Iris has surrounded herself with a family of flowers. Propagating her daylilies and roses and tending to a garden that helps her keep memories of those she loved alive.
In the early 2000s, Abby is a young mother whose husband has recently returned from military service in Iraq. When Abby’s family rents a cottage along Lake Michigan, next door to Iris’ property, the older woman can’t help but view the young family as a window to the life she once had.
As Iris and Abby are drawn together by their shared love of flowers, the friendship that blossoms between them is a testament to the healing power of both gardening and human connection.
The Book Girls Say…
This book is an interesting look at PTSD for soldiers returning from war, and its effect on the soldier’s family. The comparisons between the 1940s & 2000s add an additional discussion point.
Readers particularly enjoy the audio version of this heartwarming book because of the two different narrators who read for Iris and Abby. Keep the tissues nearby as you read because you’re sure to shed a few cathartic tears during the ultimately uplifting tale.
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Books Set in the 2000s
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The Star-Crossed Sisters of Tuscany
Book Girls’ Readers Rate This Book
98% Would Recommend to a Friend
Book Summary
Do you dream of seeing the Venetian canals, the Amalfi Coast, or wandering through gorgeous Tuscan villages? This novel will transport you to all three dramatically different scenic Italian locations in vivid detail.
Two hundred years ago, Filomena Fontana cursed her sister. Ever since then, every 2nd born sister in the Fontana family has been unable to find love.
Some of the women believe in the curse, and others are skeptical, but when eighty-year-old Aunt Poppy invites two of the twenty-something second-born sisters to return to Italy with her, promising to have a plan to break the curse, they can’t pass up the chance. The trio of women travel throughout Italy, learning about their family history and uncovering secrets.
The Book Girls Say…
If you’re looking for a book to get lost in, this is a charming and light read filled with vivid atmospheric details! The narrator’s Italian accent makes the audiobook especially enjoyable.
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Book Summary
Alberto knows he is an old man now, but he doesn’t know how old. In fact, he doesn’t even know his birthday. He arrived at an orphanage during the Spanish Civil War and remembers nothing about his childhood before that time.
His 7-year-old Grandson, Tino, is surprised to learn that his grandfather has never had a birthday party, received presents, or blown out candles on a cake. But he wants this to change, so Alberto and Tino set out on an adventure to find Alberto’s birthday.
The hunt for his past takes them into the heart of Spain, transporting you back to the Spanish Civil War as they work through details from Alberto’s difficult childhood.
Orphan Train
Book Girls’ Readers Rate This Book
99% Would Recommend to a Friend
Book Summary
During the 80 years leading up to the Great Depression, so-called Orphan Trains transported children from cities on the East Coast to the farmlands of the Midwest. The fates of the children on board – whether they would end up with loving families or end up with a childhood of hard labor – were determined by pure luck.
Vivian – now 91 – was one of those children, and her childhood memories are now tucked inside trunks in her attic. Eighteen-year-old Molly is aging out of the foster care system and is assigned community service helping the elderly Vivian clean out her home. She will soon learn that the two have much more in common than she ever expected.
The Book Girls Say…
Melissa read Orphan Train a few years back and was shocked to learn about the Children’s Aid Society trains. While some have criticized the book as seeming like a young adult novel, Melissa enjoyed the story and characters.
The Library of Lost Love
Book Summary
Joan has grown a bit too comfortable staying inside her Notting Hill home alone now that she is in her upper seventies. Her recently widowed neighbor and friend, Pamela, encourages Joan to take on a young lodger for some company.
Twenty-something Jess loves her job running an independent cinema, but sales are down and she’s worried about her job. Worse, her ex-boyfriend just ran off with her savings, and she’s temporarily staying with her married friends. It’s time to find a new living arrangement, and Joan’s room for rent might be perfect!
Despite being from different generations, Joan and Jess understand each other. Soon, they’re testing out adopting each other’s lifestyles. Jess shows Joan how to use Facebook and email, while Joan helps Jess detach from the online world and look for love in real life.
The Book Girls Say…
Readers say this story is slow-paced and sentimental. It’s a good read when you need something sweet and a bit predictable. The heart of the story is friendship, but both characters are also trying to find love, so there are some romance storylines for each of them as well.
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Harry’s Trees
Book Girls’ Readers Rate This Book
97% Would Recommend to a Friend
Book Summary
Thirty-four-year-old Harry has always loved trees, but he spends his days behind a computer as an analyst in a treeless US Forest Service office. After his wife dies suddenly and tragically, Harry can’t seem to move forward. One day, he decides to follow his wife’s advice – he quits his job and escapes to the remote woods of northeastern Pennsylvania to be with the trees.
There, he meets Oriana, a 9-year-old girl who has suffered a significant loss of her own. She spends most of her time in the forest with her book in the treehouse her father bought for her. They bond over their love of the forest and the trees.
The octogenarian town librarian gives Oriana a strange, handwritten book called The Grum’s Ledger. With this book as their guide, Oriana helps Harry believe in the magic, if only he’s willing to open his eyes and see it.
The Book Girls Say…
Because of its thread of magical realism, some describe this book as a fairy tale for adults. But it’s more than that. It’s a story of grief, sadness, and the power of friendship and connection set against the beauty of Pennsylvania’s Endless Mountains. This story is told from many points of view, including Harry and Oriana’s, as well as numerous others – but it’s written in a way that it’s easy to follow and understand.
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30 Best Magical Realism Books
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The Lost Ticket
Book Girls’ Readers Rate This Book
97% Would Recommend to a Friend
Book Summary
Twenty-nine-year-old Libby is in her own world as she arrives in London, broken-hearted and newly unemployed. The first person she meets is an elderly man named Frank on a bus. Frank explains that he met a beautiful girl on bus 88 in 1962, and they made plans to visit the National Gallery together. But then Frank lost the ticket with her phone number. So, every day for 60 years, he’s ridden the same bus, hoping to run into her again.
Libby can’t just walk away from such a romantic and heartbreaking story. She enlists the help of an unlikely companion and creates posters advertising their search for the mystery girl. As they try to find her, Frank’s dementia is progressing quickly, teaching Libby important lessons about embracing happiness before it’s too late.
The Book Girls Say…
The search for the mystery girl pulls you in right away, but the side characters are just as delightful as Libby and Frank. The audio is excellent, with the narrator nailing the personalities of each character perfectly. There’s also an unexpected twist, so don’t read too many other reviews to avoid spoilers!
This book is titled “The Girl on the 88 Bus” in the UK.
Another fun option by this author that fits the prompt is Nosy Neighbors.
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Take It From Me
Book Summary
Harper is a young author with one major best-seller under her belt, but now she’s in need of a career comeback. At the suggestion of her agent, she rents a house in New Canaan, Connecticut. Hiding her author identity from everyone she meets, Harper seeks to draw inspiration for a new novel about women in the suburbs.
Soon Harper befriends her empty-nester neighbor. It’s October, and Wendy’s son just moved away for college. She’s struggling with being all alone. But not just because she misses her son. Wendy is keeping a secret of her own – her struggle with kleptomania.
The Book Girls Say…
Angela was initially drawn in by the novel’s focus on kleptomania and mental health, which was very well done. Ultimately, however, she enjoyed the story’s intergenerational relationship element the most.
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The Library
Book Girls’ Readers Rate This Book
100% Would Recommend to a Friend
Book Summary
Teenager Tom uses the library to escape from an unhappy present and what feels like an unhappy future, stuck working at the dog food factory. Seventy-two-year-old Pensioner Maggie finds him suspicious.
She’s been alone for ten years now and tells herself she is happy. When she has to be rescued by Tom, an unlikely friendship begins. As Maggie teaches Tom to stand up for himself, Tom helps Maggie realize that her future doesn’t have to be defined by her past.
Together, they’re an unstoppable force when they set out to prove that the local library is about so much more than books.
The Book Girls Say…
Reviewers say that while this book addresses some heavy topics, it’s also a very sweet story full of heart.
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The Summer Seekers
Book Girls’ Readers Rate This Book
96% Would Recommend to a Friend
Book Summary
Kathleen is living independently at 80 years old, and she’s rather impressed with the way she handled a recent scary situation with an intruder. However, her daughter Liza thinks this incident is a prime example of why Kathleen should move to a senior home.
Not only does Kathleen not want to move, she’s also ready for a new adventure traveling down Route 66 in search of an old friend. Liza’s already stressed and has no time to drive across the country with her mom. So, Kathleen publishes an ad for a driver and companion to travel with her across America.
When 25-year-old Martha sees the ad, she thinks it could solve all her problems. How much trouble could an 80-year-old be?
The Book Girls Say…
This story is light and enjoyable – nothing overly dramatic or weighty. It’s just three women, at various stages of life, having the courage to reassess and take stock of their lives and make necessary changes. This work of women’s contemporary fiction has a romance storyline as well.
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The Lightkeeper’s Daughter
Book Girls’ Readers Rate This Book
100% Would Recommend to a Friend
Book Summary
Set on beautiful Lake Superior, this book explores a family’s history and deep connection to a lighthouse. Elizabeth lives in a senior home and has a sharp mind, but has lost her sight. She fills the void with music and memories, which spring to life when her late father’s journals are found in the ruins of an old shipwreck.
Morgan is a troubled teen assigned to community service at Elizabeth’s home. With her help, Elizabeth reads through her father’s journal, with each entry taking Morgan and Elizabeth back in time 70 years. He was the lighthouse keeper on isolated Porphyry Island. As the unlikely duo reads, they realize their fates are connected to the remote island and each other in unexpected ways.
The Book Girls Say…
Don’t miss the author’s notes at the end of the book! She explains more about the real lighthouse and Lake Superior. One reviewer notes that there is more swearing than she expected based on the cover, so keep that in mind if you’re sensitive to language.
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The Switch
Book Girls’ Readers Rate This Book
95% Would Recommend to a Friend
Book Summary
When twenty-nine-year-old Londoner Leena Cotton is forced to take a two-month sabbatical from work after a disastrous presentation, she escapes to her grandmother’s house in a small village in Yorkshire, England. Her grandmother, Eileen, is about to turn 80 and hopes her next decade might include a second chance at love. Convinced that her grandmother will have better luck in the romance department if she heads to the big city, Leena convinces Eileen to swap places with her and move into Leena’s London apartment.
This warm and charming novel is filled with vibrant descriptions of London and English village life as the grandmother and granddaughter duo aim to reset their lives after a difficult loss.
The Book Girls Say…
Although Eileen’s search for love plays a role in this story, we wouldn’t describe this book as a romance. Instead, it’s a character-driven story about a wide variety of relationships.
We recommend the audio version for the full experience with accents!
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The Reading List
Book Girls’ Readers Rate This Book
97% Would Recommend to a Friend
Book Summary
When teenage library worker Aleisha finds a list of little-known novels in the back of To Kill a Mockingbird, she decides to read every book on the list. Each story is magical to her for different reasons.
Widower Mukesh worries about his bookworm granddaughter, Priya. To connect with her, he visits the library and meets Aleisha. When she shares the found list with him, they begin to form an unexpected friendship and discover the healing that is desperately needed for each of them.
Also Featured on These Book Lists:
Novels with Characters Connecting Through Books
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Readers’ Favorite Books: 2023 Edition
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Printable Version of the Challenge Booklists
Readers who support The Book Girls’ Guide through our Buy Me a Coffee (BMAC) membership site as Inner Circle or BFF members can access printable versions of the reading challenge book lists. As we update the Lifetime of Reading Challenges throughout the year according to the challenge schedule, the lists will become available in a single-page printable format for our BMAC members.

We offer two membership levels. Both our BFF members and our Inner Circle members get access to the single-page printables for the year-long reading challenges. Visit our Buy Me a Coffee membership page for a full list of benefits for each level.
Our BMAC members help cover the cost of running the challenges so we can keep them free for everyone!
Book Lists By Character Age
Links to our book recommendations for all twelve of the Lifetime of Reading challenge prompts can be found below:
- Books Spanning a Character’s Lifetime
- Books With Characters in Their 90s and 100s
- Books With Characters in Their 80s
- Books With Characters in Their 70s
- Books With Characters in Their 60s
- Books With Characters in Their 50s
- Intergenerational Novels: Books that Connect Generations
- Books With Characters in Their 40s
- Books With Characters In Their 30s
- Books with Characters in Their 20s
- Books with Teenage Characters
- Books with a Child Protagonist (Bildungsroman Novels)
More Books to Consider
Because intergenerational relationships are such a beloved storyline, many of the books on the 60, 70, 80, and 90-100-something lists would also fit this month’s prompt. In many cases, it was hard to decide where to slot books. So, feel free to revisit those lists as well.
We hope you enjoyed this book list and found several books to add to your TBR (to be read list). If you’re choosing a book for our reading challenge, you are also welcome to read any other book that meets the challenge prompt.
If you have a suggestion for a book that you think would be a great addition to this list, please fill out this form.

