8 of the Best Books About Intergenerational Friendships

Some of the most valuable friendships I’ve ever had are with those a few decades older than me. I appreciate listening to their insights on challenges that I might be facing for the first time but that they have encountered before and can see from a more long-term perspective. Hopefully, I also give them a unique take on subjects that friends of their own age might approach in a different way.

Stories about intergenerational friendships, too, have plenty of wisdom for readers to gain. They offer a reminder that people are often alike in ways they might not expect and that there is much to learn from those born in a different generation than you. These eight fiction books all center intergenerational friendships, from contemporary fiction to cozy mysteries and more.

For more perspectives on the many shapes friendship can take, read contributor Laura Sackton’s An Ode to Bookish Internet Friends. In this moving essay, she reflects on the connections she’s made through online communities and how they’ve enriched not only her reading but her personal life. Plus, find more recs for Books About Female Friendships, including Brown Girls by Daphne Palasi Andreades and Heavy Vinyl by Carly Usdin, Nina Vakueva, Irene Flores, Rebecca Nalty, and Jim Campbell.

Now, let’s jump into my recommendations for books featuring intergenerational friendships.

Book cover of All the Lonely People by Mike Gayle

All the Lonely People by Mike Gayle

When octogenarian Hubert Bird’s daughter Rose announces she’s coming for a visit, he’s equally thrilled and nervous to see her. He’s spent years lying to Rose about all the friends he doesn’t have when in reality, he finds himself isolated and unhappy.

To put things right, he scrambles to make new friends in his community before Rose arrives — and he finds them in unexpected places.

Sophie Go’s Lonely Hearts Club coverSophie Go’s Lonely Hearts Club cover

Sophie Go’s Lonely Hearts Club by Roselle Lim

After becoming a professional matchmaker, Sophie Go struggles to start her new career or forget a traumatic event that happened while training. Desperate for new clients, Sophie is thrilled to come across the Old Ducks: a group of seventysomething men who are looking for a second chance at love.

As Sophie helps them find potential soulmates, she learns valuable truths about connection and healing.

Here we go again coverHere we go again cover

Here We Go Again by Alison Cochrun

Logan Maletis and Rosemary Hale, ex-friends turned rival high school teachers, struggle to process the news that their mentor and former English teacher, Joe Delgado, only has months to live. But that’s not the only surprise Joe has to share. He’s also determined to go on one last road trip to his old house in coastal Maine, and he wants Logan and Rosemary to come with him.

On the road, Logan and Rosemary must not only celebrate Joe’s rich and complicated life — as well as honor its end — but reconcile their difficult feelings for each other.

Vera Wong's Unsolicited Advice for Murders by Jesse Q. Sutanto book coverVera Wong's Unsolicited Advice for Murders by Jesse Q. Sutanto book cover

Vera Wong’s Unsolicited Advice for Murderers by Jesse Q. Sutanto

Between her husband’s death and estrangement from her adult son, Vera Wong finds herself often alone in her tea shop. That all changes when, one morning, she discovers a dead body on the floor.

Confident that she can do a better and faster job than the local police, Vera investigates the murder herself. Along with possible suspects, she also meets new friends who bring her life a renewed vibrancy.

Skye Falling book coverSkye Falling book cover

Skye Falling by Mia McKenzie

Twelve years after donating her eggs, 38-year-old Skye Ellison is unexpectedly contacted by a tween girl named Vicky who introduces herself as “Skye’s egg.” Although initially reluctant to connect, Skye decides it couldn’t hurt to get to know Vicky and her family.

Inspired by their unlikely friendship, Skye asks herself complicated questions about belonging and the people she wants to be a part of her life.

cover of The Secret Life of Albert Entwistle by Matt Caincover of The Secret Life of Albert Entwistle by Matt Cain

The Secret Life of Albert Entwistle by Matt Cain

Forced to retire from his beloved post office job, Albert Entwistle dreads the added time to process his mother’s death and the loneliness he feels as a closeted gay man. But when he befriends a single parent named Nicole, he confides in her about his first love George.

Nicole is determined to reunite the two and helps Albert cope with his social anxiety as they search for George, giving him the confidence he needs to come out and process his traumatic childhood.

The Mostly True Story of Tanner and Louise coverThe Mostly True Story of Tanner and Louise cover

The Mostly True Story of Tanner and Louise by Colleen Oakley

Twentysomething Tanner Quimby and octogenarian Louise Wilt become reluctant roommates when Tanner is hired as a live-in caretaker. Louise has her quirks, but Tanner doesn’t suspect what they all add up to until the elderly woman wakes her up in the middle of the night and bribes her to leave town with her.

Feeling lost to her life’s purpose and longing for adventure, Tanner agrees. The two embark on a cross-country joyride with secrets waiting to be unraveled on the road.

To fill a yellow house coverTo fill a yellow house cover

To Fill a Yellow House by Sussie Anie

After moving to a new neighborhood in London, 14-year-old Kwasi struggles to connect with his classmates. But he finds an unexpected friend in charity shop owner Rupert, who has been adrift since the death of his wife and sees promise in Kwasi’s artistic talent.

Try 10 of the Best Nonfiction About Friendship for Adults for more books that explore what it means to be a true friend, including Girl Squad by Sam Maggs.

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