The best novels about surviving inconsolable heartbreak

Who am I?

I grew up in a woodsy Massachusetts town, then spent the first decade of my adult life striving to succeed as a painter in New York--while reading fiction as if inhaling another form of oxygen. In my thirties I traded paintbrush for pencil, persevering until I published my first novel at 46. I've now written six novels and a story collection about the volatile bonds of modern families, through marriages, births, betrayals, illnesses, deaths, and shifting loyalties. I love to tell a single story from multiple perspectives, ages, and genders; to inhabit a different vocation in each new character: bookseller, biologist, pastry chef, teacher. Like actors, fiction writers love slipping into countless other lives.

I wrote...

Three Junes

By Julia Glass,

Book cover of Three Junes

What is my book about?

My first novel follows a Scottish father and son, Paul and Fenno, and a young American artist, Fern, who meets the two men on opposite ends of a decade. It begins in Greece, where Paul has fled after his wife's death—and ends on Long Island, where Fern, also widowed, ponders what to do about a surprise pregnancy. At the center stands Fenno, a bookseller in Greenwich Village, who receives a strange gift that forces him to confront the fear and heartbreak of living as a gay man at the height of the AIDS epidemic. 

I wrote this book after enduring, in one year, divorce, the loss of my only sibling to suicide, and cancer treatment. I realized that all the most powerful fiction is about how we survive devastating grief and rediscover hope.

The Books I Picked & Why

Shepherd is readers supported. When you buy through links on our website, we may earn an affiliate commission. This is how we fund this project for readers and authors (learn more).


By Josephine Wilson,

Book cover of Extinctions

Why this book?

Confession: I bought this novel partly for its gorgeous floral jacket...a bait-and-switch for the emotional claustrophobia in which it begins. I fell in love with it because of how deep I was drawn into lives I didn't think I could care about. Fred, a retired engineering professor--wife deceased, son severely disabled, adoptive daughter estranged--has banished himself to wither self-righteously away in a retirement village. But circumstances force him to let someone in: his neighbor, Jan, who's suffered her own misfortunes yet leads the most engaged life she can.

Set in Australia, this increasingly exhilarating and witty novel shows how it's never too late to face down eviscerating truths, make amends, and flout conventions; also, how friendships can save us (as I learned during my year of heartbreak). As a writer, I was stunned by an extended real-time scene in which an automotive mishap lands Jan and Fred in a glamorous restaurant where, as they drink the night away, Jan puts Fred through a soul-scorching confrontation about his cowardice. Reading this book a second time, I loved it just as much.


By Andrew Holleran,

Book cover of Grief

Why this book?

For my generation in New York, the Plague Years were the equivalent of war, so many battles fought, too many lost, and those who lived through it all as scarred as any veterans of wars fought with guns. Doing volunteer work in the gay community put me close to the battle lines, and I read fiction about the time to help me honor the ghosts. This brief, exquisite, often surprisingly funny novel is an elegy to all that loss. It came out not long after my own novel set in that era, and I wanted to read about characters who, like mine, were "survivors," feeling more guilt and sorrow than relief.

A solitary man moves from Florida to Washington to make a fresh start after his mother's death. He rents a room in an elegant house where he becomes fascinated by his landlord--another lonely gay man--and, through a book left in his room, by the tragic life of Mary Todd Lincoln. The protagonist's wanderings through Washington create a tapestry in which the warp is American history itself and the woof is the legacy of so many men who, still young, have attended too many funerals.

Year of Wonders: A Novel of the Plague

By Geraldine Brooks,

Book cover of Year of Wonders: A Novel of the Plague

Why this book?

Before there was Covid-19, well before Hamnet, there was Geraldine Brooks's astonishing debut novel, based on historic accounts of an English village that quarantined itself in 1666 during the Black Plague. When Brooks, an accomplished journalist, couldn't find enough source material for a nonfiction book, she struck off into fictional territory--and (lucky us, her readers) has never looked back. I read the novel when I was asked to present her with an honorary award. She'd already written more novels and won a Pulitzer, but I went back and read this one first. It's told through the eyes of Anna, a villager who loses both of her young children to this grisly disease and must find a new purpose. The depth of heartbreak we witness is nearly unbearable, but Anna--through passion, danger, and finally a voyage that takes her far from home--prevails. Brooks's imagination is peerless.

The Unmade World

By Steve Yarbrough,

Book cover of The Unmade World

Why this book?

Like Three Junes, this richly peopled and plotted novel takes place over ten years and in far-flung locales (Poland, California's Central Valley, and upstate New York among them), told through the eyes of two very different men involved in a terrible accident. Richard, a journalist visiting Poland, survives a car crash in which his wife and daughter die; Bogdan, a small-time thief responsible for the collision, flees the scene. As Richard, haunted by the face of the man who fled, tries to find solace in his work, and as Bogdan's life and marriage collapse, we travel with them through numerous twists of fate on both sides of the Atlantic, including a murder-suicide case that Richard must help solve.

What astonished me most was how deeply I grew to care for both the "good guy" and the "bad guy"--and how much suspense I felt as I followed them over so many years. As a reader, I experienced grief, terror, hope--and laughter. Because that's the key to the best stories about unthinkable tragedies: they've got to make you laugh along the way.

Dear Edward

By Ann Napolitano,

Book cover of Dear Edward

Why this book?

I'm not generally attracted to fiction about teenagers--and who relishes reading a story revolving around a plane crash?--but my topsy-turvy mindset during peak pandemic led me to this one, thanks to a recommendation from a trusted bookseller. (Forget reviews. The more smart booksellers you have in your life, the more good books you'll read.)

Twelve-year-old Edward is the sole survivor of an airliner crash in which his mother, father, and brother are killed. After recovery from grave injuries, he moves in with a childless aunt and uncle, must attend a new school, and try to escape macabre publicity for his "celebrity" status. Over the next few years, an essential friendship keeps him moving forward--until the discovery of something that his uncle has hidden from him rips his heart open anew. The consequences are breathtaking. I haven't wept so hard at an ending in years.

Closely Related Book Lists

Distantly Related Book Lists