The best books about finding or losing love in old age

Who am I?

Widowed at age fifty and now eighty-four, I know first hand the search for love in late life. I have three adult children and can't avoid bringing baggage to any new relationship, whether with humans or the cats I adore. Coming to writing seriously only after my husband’s death, I remain fascinated by questions of craft, how the story is told (as my recommendations show), and I’ve published several essays on aspects of that subject. My first career in dance, my conversion to Catholicism, and my psychoanalytic therapy have been major parts of my life and play significant roles in my memoir, my novel, and my more recent novella and stories.


I wrote...

Side by Side but Never Face to Face: A Novella & Stories

By Maggie Kast,

Book cover of Side by Side but Never Face to Face: A Novella & Stories

What is my book about?

In these linked stories Maggie Kast asks, “Can new love be found in old age?” Greta, her narrator, has been wrenched from a long and tightly-circled marriage to Manfred, an Austrian Holocaust survivor. With different backgrounds, they sometimes abrade each other, but the friction strikes sparks, and the marriage remains vital. This book will open your heart to love that endures, transcends fear, dissolves old ideas of desire, and invites new desiring.

Says Garth Greenwell, author of Cleanliness and What Belongs to You, “Maggie Kast has a gift for illuminating her characters’ inner lives, and these beautiful stories, as they shuttle gracefully between past and present, Europe and America, strike a profound and satisfying balance between intimacy and mystery...a wise and powerful book.”

Shepherd is reader supported.

When you buy books through our website, we may earn an affiliate commission. Please help us make book discovery magical and join our membership program.

The books I picked & why

Oh William!

By Elizabeth Strout,

Book cover of Oh William!

Why this book?

The quiet, mesmerizing voice of Strout’s Lucy Barton tells of getting to know her first love truly and deeply long after their marriage has ended. The book accomplishes the difficult task of making the improbable seem believable. It affirms my use of unlikely events in my own stories, making fiction more like life. In my life as a dancer and now as a writer,  I am always moved by art that is not set apart, high on a pedestal, but takes place right in the middle of life’s messy events.

Oh William!

By Elizabeth Strout,

Why should I read it?

2 authors picked Oh William! as one of their favorite books, and they share why you should read it.

What is this book about?

THE TOP TEN SUNDAY TIMES BESTSELLER

The Pulitzer Prize-winning, Booker-longlisted, bestselling author returns to her beloved heroine Lucy Barton in a luminous novel about love, loss, and the family secrets that can erupt and bewilder us at any point in life

Lucy Barton is a successful writer living in New York, navigating the second half of her life as a recent widow and parent to two adult daughters. A surprise encounter leads her to reconnect with William, her first husband - and longtime, on-again-off-again friend and confidante. Recalling their college years, the birth of their daughters, the painful dissolution of…


The Friend

By Sigrid Nunez,

Book cover of The Friend

Why this book?

A dear and lifetime friend commits suicide. Instead of a note, he bequeaths to the narrator a large and faithful new friend, this one four-legged and furry. I delight in how the narrator gets inside the emotional subtleties of this new relationship and then explores other loves of people for their pets. A delicious metafictional spin to the end of this realistic tale (no spoilers here!) made me go back and read it from the beginning again.

The Friend

By Sigrid Nunez,

Why should I read it?

5 authors picked The Friend as one of their favorite books, and they share why you should read it.

What is this book about?

A moving story of love, friendship, grief, healing, and the magical bond between a woman and her dog.

WINNER OF THE 2018 NATIONAL BOOK AWARD * A NEW YORK TIMES BESTSELLER * SHORTLISTED FOR THE 2020 INTERNATIONAL DUBLIN LITERARY AWARD

'A true delight: I genuinely fear I won't read a better novel this year' FINANCIAL TIMES

'Loved this. A funny, moving examination of love, grief, and the uniqueness of dogs' GRAHAM NORTON

'Delicious' SUNDAY TIMES 100 BEST SUMMER READS

When a woman unexpectedly loses her lifelong best friend and mentor, she finds herself burdened with the unwanted dog he has…


Book cover of Through the Shadowlands: The Love Story of C. S. Lewis and Joy Davidman

Why this book?

As a Catholic convert myself, I have long been interested in the spiritual journeys of these two, a middle-aged, conservative English professor and a young divorcee with two sons. Actually, two unlikely loves play out in this non-fiction biography: first young Lewis with Mrs. Moore, thirty years his senior (who may or may not have been his lover), and much later Joy, a Jewish convert to Christianity and former communist. Her death, just four years after their marriage, is mourned in Lewis’ own book, A Grief Observed, the only book I found comforting after my husband died. 

Through the Shadowlands: The Love Story of C. S. Lewis and Joy Davidman

By Brian Sibley,

Why should I read it?

1 author picked Through the Shadowlands as one of their favorite books, and they share why you should read it.

What is this book about?

At first glance, they were an unlikely couple: C. S. Lewis, a distinguished author and Oxford scholar, and Joy Davidman, a Jewish-American divorcée, converted Christian, mother of two, and former Communist Party member. But together they walked through life's challenges, persevering despite having their faith tested in the face of suffering and death. This amazing true story reveals the many events that occurred in the lives of two astounding Christians to bring them together and spark their love for each other. Readers will experience both their tender moments and the darkest hours where faith was tested and shaken to its…


Love Medicine

By Louise Erdrich,

Book cover of Love Medicine

Why this book?

My parents were anthropologists who took me as a pre-teen to visit the pueblos of the southwest. There we attended ritual dances, and I was deeply impressed by their devotion, beauty, and power. I incorporated those impressions into the modern dance I was studying and would continue to practice as my first career. Now as a writer I continue my interest in indigenous cultures, and I admire the way the Plains Ojibwe, as portrayed by Erdrich, expand the meaning of “medicine” beyond scientific facts. “Medicine” comes to mean love, the healing force that overcomes envy and anger in communities from the plains to the pueblos to families around the world, including my own.

Love Medicine

By Louise Erdrich,

Why should I read it?

1 author picked Love Medicine as one of their favorite books, and they share why you should read it.

What is this book about?

“The beauty of Love Medicine saves us from being completely devastated by its power.” — Toni Morrison

Set on a North Dakota Ojibwe reservation, Love Medicine—the first novel from master storyteller and National Book Award-winning author Louise Erdrich—is an epic story about the intertwined fates of two families: the Kashpaws and the Lamartines.

With astonishing virtuosity, each chapter of this stunning novel draws on a range of voices to limn its tales. Black humor mingles with magic, injustice bleeds into betrayal, and through it all, bonds of love and family marry the elements into a tightly woven whole that pulses…


Book cover of Falling in Love When You Thought You Were Through: A Love Story

Why this book?

This true story of love and lasting marriage in later life is told by the husband and wife in alternating first-person voices. Ingrained habits of social and personal life and relationships with both parents and children all create stumbling blocks as the two lovers strive to create a unified way of life. I admire this book for its frank and vivid presentation of the pitfalls that can threaten a union of two individuals who meet in late middle age, already well set on their paths. In its presentation of problems and solutions, this book offers the most “self-help” of these five recommendations.

Falling in Love When You Thought You Were Through: A Love Story

By Jill Robinson, Stuart Shaw,

Why should I read it?

1 author picked Falling in Love When You Thought You Were Through as one of their favorite books, and they share why you should read it.

What is this book about?

Jill Robinson, the author of Bed/Time/Story and Past Forgetting, and her husband, Stuart Shaw, share their true story about finding love when they both had lost faith in romance.

When Stuart and Jill first met, neither felt ready for love. Stuart was recovering from the alcoholism that had wrecked his marriage and ravaged his career. Jill was recovering from a second failed marriage and believed she was done with love forever.

But then, in a crowded Connecticut diner, Jill caught Stuart's eye and shot him a look that she knew would draw him in. What follows is a sexy journey…


5 book lists we think you will like!

Interested in family secrets, North Dakota, and alcoholism?

8,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about family secrets, North Dakota, and alcoholism.

Family Secrets Explore 126 books about family secrets
North Dakota Explore 14 books about North Dakota
Alcoholism Explore 68 books about alcoholism

And, 3 books we think you will enjoy!

We think you will like The Virgin Suicides, The Stories of John Cheever, and How Dogs Love Us if you like this list.