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Image: Stuart Simpson/Penguin

Mark Twain once said, “Age is an issue of mind over matter. If you don't mind, it doesn't matter.” And both minds and matters can come to a head in one's fifties, when middle-age introduces a means of looking back over the life you've lived so far as well as casting forward to what else lies ahead.

Marriages may be crumpling or coming back together after children leave the nest, mid-life crises lurk and new leases of life are on the horizon. Literature has covered them all – and more besides. Here are the best books to read before the big Six-Oh. 

Nora Webster by Colm Tóibín (2014)

This, really, is an ode to grief and human resilience, and the shoots of new life that can sprout from within. It's all about Nora, as you might have guessed, a middle-aged widow cast adrift by the premature death of her beloved husband in 1960s Ireland.

With four children still under her wing (the two eldest now at college), and in a small town where your business is never just your own, Nora must navigate her new life without the love of her old one. She has no savings, a meagre pension, and neighbours who know far more about her life and past than anyone would like. 

But, as the years pass, and her family dynamic evolves (against the backdrop of the messy Irish politics of the time), she finds salvation in music, friendship and the dawning sense of her newfound independence. “She had to remind herself that she was free now,” Tóibín writes, “that there was no Maurice who would be cautious about costs, and grumpy about anything that would cause disruption to his routine. She was free.”

Breathing Lessons by Anne Tyler (1988)

This is the novel that won Anne Tyler a Pulitzer Prize in 1989, and within the first few pages you'll see why. Told across a single summer's day, as Maggie and Ira, married and middle aged, drive from Baltimore to Pennsylvania for the funeral of a friend.

Through the course of the road trip, thanks to a series of unexpected detours via old friends and their grown up children, they are forced to confront the meaning of their marriage head on: its successes, its failures and the niggling old scores they've never quite got round to settling.

What emerges is a tender and vivid portrait of a 28-year marriage painted in hard-earned truths – the expectations and disappointments; the secrets and lies; the changing winds of love through time. And ultimately, thanks to Tyler's scintillating prose and profound wisdom, we are exposed to the way a husband and wife can fall in love, again and again and again.

As the author Edward Hoagland wrote, “[Tyler] is interested not in divorce or infidelity, but in marriage – not very much in isolation, estrangement, alienation and other fashionable concerns, but in courtship, child raising and filial responsibility.”

Jake's Thing by Kingsley Amis (1978)

So, Jake's titular “thing” is... yes, it's his penis. He's a 59-year-old Oxford don with a malfunction in the trouser department. His marriage is on the rocks, too. Not that that's the source of his problem, nor is his problem the source of his marital funk (actually, he is the source of both).

Because also, his other “thing” is his numbingly misogynistic attitude to women. And then there's his “thing” for modern culture, too, which he detests ("If there's one word that sums up everything that's gone wrong since the war, it's 'Workshop.' After 'Youth,' that is," he harrumphs).

So Kingsley Amis' Jake is a lot of things, but one thing he's not is a particularly nice guy. And this only gets worse after he endures a humiliating bout of sexual therapy, revisits an old flame and runs into an angry feminist protest against his college's sexist admission policy.

Shortlisted for the Booker Prize in 1978, this social satire presents a view of older age that none of us should aspire to. He is a man being left behind by progress, unwilling to adapt to the “new ways”, stuck on a concrete island of stubborn repression. But then, we all know someone a bit like Jake. Don't we?

The Joy Luck Club by Amy Tan (1989)

This heart-caressing gift of a novel is about four immigrant Chinese women who meet weekly in San Francisco to play mahjong, trade stories about what they've left behind in China, and gossip about their children. They call themselves The Joy Luck Club.

Although Suyuan, Ying-ying, An-Mei, and Lindo each have a story of painful suffering in their native China, they love their homeland even from thousands of miles away. And they're desperate to pass their culture down to their daughters. Only, their four daughters are only interested in looking like, and being accepted by, Americans. And there lies the rub.

Amy Tan's intensely poetic prose brings these women, and their stories, beautifully to life in a novel that will speak to any women with adult daughters. It's about mothers and daughters, memory and keeping alive your past in your children. It's also about making a new life in a new country without ever losing sight of your heritage.

The Epic of Gilgamesh by Unknown (2100 B.C.)

Some might say one's fifties is a time to look back, reflect and appreciate (if not wonder) where it all began. Let's start, then, with the world's oldest literary text. 

Written on clay tablets about 4,000 years ago, it's a tale about a tyrannical Sumerian King who makes a new best friend, Enkidu – sent by the gods to straighten him out. The pair go on tremendous adventures together. But when Enkidu dies, Gilgamesh realises his own mortality. Grief-stricken at the idea, he sets off on a quest for immortality.

It's a wild ride, stuffed with fighting monsters, apocalyptic floods, nymphomaniacal gods and youth-giving plants. But behind all the action lies a story about wisdom and folly, love and sex (so much sex, including one uninterrupted act of coitus that lasts for a week), family and the power of friendship.

But, above all, it's about humankind's eternal struggle with the fear of death. Gilgamesh ultimately fails in his hunt for immortality. But he nevertheless finds salvation in coming to terms with the dreadful knowledge that he, like all of us, must die.

Spring by Ali Smith (2019)

Time is a central concept to the Seasonal Quartet, the four books (Autumn, Winter, Spring and Summer) written at rapid pace between 2016 and 2020, and reflecting the real-time events thereof. And while each features someone nearing the end of their life, and often at least another character much younger, it is in Spring that middle-age is best explored.

Through Richard we learn of the effervescent - and dying - Paddy, a screenwriter and brilliant mind whom Richard has loved and lost. While Spring deals with renewal, Smith also investigates the relics of winter’s demise: Richard, brilliant last in the 70s and 80s, is scruffy and bereft.

A messy divorce left him separated from his daughter, and conversing with an imaginary one instead. Still, as Spring shows, new shoots emerge all the time. In spite of national turmoil and against a backdrop of punitive immigration policy, he finds his creativity in unlikely places.

Never Change by Elizabeth Berg (2001)

Myra Lipinski is one lonely old soul. Well, not that old. She's only 51. But she's been lonely so long that she knows no other way. She trained as a nurse "because I knew it would be a way for people to love me." Still, no dice. Now a self-anointed spinster it's just her and her dog, Frank. And also her patients, an eccentric bunch whom she home visits throughout the week.

But then, her dinner-for-one existence is rattled when an old school crush appears as her patient. Chip Reardon was her high-school dreamboat; way out of her ugly-duckling league. But he's not so dreamy now – he's dying of cancer. The pair soon strike up a friendship based on their mutual loneliness, and romance buds. For the first time in Myra's life, she finds herself in a loving relationship, albeit with a man who's days are numbered.

And from this comes a life-affirming realisation: that her loneliness wasn't fate at all. It was choice. We're born alone and then we die, and what gets us through all the successes and failures in between, ultimately, is connection. Connection to oneself and to others.

Fried Green Tomatoes at the Whistle Stop Cafe by Fannie Flagg (1987)

A middle-aged women whose marriage is in tatters forms an unlikely friendship with an old lady in a nursing home, in this classic of queer literature that wraps you into its world like a hug.

Evelyn Couch is a woman adrift. But when she meets Cleo Threadgood in an Alabama nursing home, the 80-year-old's stories about her life in a nowhereville town breathe life into her exhausted soul.

It is a delightful tale of family, aging, lesbianism, and the brutalising effects of racism in Deep South America, at the heart of which is a gorgeous story about the love affair between Ruth and Igdie, owners of The Whistle Stop Cafe.

Too much happens to do the story true justice here, but – in essence – it is a ballad of life in small-town America that Harper Lee called "a richly comic, poignant narrative". Its message: for all life's sticks, stones and broken bones, friendship is the word that soothes us.

I Remember Nothing by Nora Ephron (2010)

“No one actually likes to admit they're old,” writes Nora Ephron. “The most they will cop to is that they're older. Or oldish.” Exactly. “In fact,” she later writes, “looking back, it seems to me that I was clueless until I was about fifty years old.”

Ephron's prose verges on poetry, her ideas explode into philosophy. So just sit back, empty your mind, and bathe in these reflections on growing older by the Queen of Growing Older.

This is the only non-novel on this list. But the final collection of essays that Nora Ephron wrote before she died defies genre, such is her mastery of language and self-expression, and is worthy of any literary list about aging.

With almost every sentence she writes, Ephron somehow manages to distil joy into its purest essence. All in, this delectably wry, dry and spit-out-your-tea funny collection of essays by the mind behind When Harry Met Sally and Sleepless in Seattle is a love letter to getting older, gracefully or not.

Nine Island by Jane Alison (2016)

Here is a deep, vulnerable and shudderingly honest meditation on what it means to be alone, post divorce. J is a middle-aged divorcee tucked away in a sun-bleached Miami apartment where she spends her days translating sex stories by Ovid into English. She has an ageing mother, an incontinent cat, and a past punctured by romantic disasters. Now, she's beginning to contemplate giving up on sex and love all together.

Through J, Alison evokes beautifully the interior life of a single woman of a certain age who – for many reasons, both personal and societal – feels invisible to the outside world. But in this story – awash with humour, irony and no shortage of watery symbolism – there is always hope. As one friendly neighbour tells her, “if you retire from love... then you retire from life.” It's up to J to choose her path.

Mrs Dalloway by Virginia Woolf (1925)

“Laying her brooch on the table, she had a sudden spasm, as if, while she mused, the icy claws had had the chance to fix in her. She was not old yet. She had just broken into her 52nd year. Months and months of it were still untouched. June, July, August! Each still remained almost whole, and, as if to catch the falling drop, Clarissa (crossing to the dressing-table) plunged into the very heart of the moment.”

That's Clarissa. We all know Clarissa. Dalloway by name, dallier by nature. She's a charmer, a dreamer, a flâneuse and a friend. A friend, that is, to all but herself.

Told across a single day, as she plans the party of her Tory politician husband, we are carried into her complex psyche as she strives to be “the perfect hostess” - to her servants, her daughter, her husband and her rejected suitor of years past. And yet, she is sinking into an existential funk.

Here is one of the greatest novels ever written about aging and change, about looking back on your life and seeing the multiple ways your life could have gone, without necessarily ruing any of it. Through Clarissa, we get a glimpse into the complexity of life and the way that small decisions can have big, unknowable consequences, both pretty and ugly. And from that sprouts an unforgettable ode to memory, dignity, survival and joy.

Chéri by Collette (1920)

“I love my past. I love my present. I'm not ashamed of what I've had, and I'm not sad because I have it no longer.” So says the ageing heroine in Colette's scandalously sexy novel about an affair between a once-famous beauty and a playboy half her age.

Léa de Lonval was one of the most beautiful courtesans in Paris. But time has finally got its claws into her, and she's facing the end of her sexual career. Not only that, but her six-year love affair with the selfish young ladies' man Fred Peloux – aka Chéri – hits the rocks when he resolves to marry a woman of his own age. But what neither expects is how deep their connection flows, and how hard it can be to let go.

This, in brief, is a delicious tale of repression, scandal, sex and desire that rattled 1920s Paris by the bed boards, not least because it was one of the first novels of its kind to celebrate female sexuality in middle age.

And, in a society that still tries to shame women for growing old, Chéri's message feels as pertinent now as it was shocking in 1920. Sex, as Colette doesn't quite say directly, does not end at 50. If anything, that's when it should improve.

The Sea, The Sea by Iris Murdoch (1978)

Charles Arrowby is an aging curmudgeon. Before we meet him, he was an irascible, pompous theatre director who's lived “a life of egoism”. Tired of that life, he gives it all up to "become a hermit: put myself in a situation where I can honestly say that I have nothing else to do but to learn to be good."

So off he trots to a creaky, wind-battered cottage on a rocky coastline to do just that. But soon, a string of blasts from the past pop up from London, and leave when they realise he's the same old bastard he's always been. Then, by pure coincidence, he bumps into his childhood sweetheart, now married, and he resolves to win her back.

The point: nothing can tame his ravenous soul. So he folds into a life of solitude, swimming in the sea, eating terrible food, and writing his memoirs. Alone. Ultimately, rather than a blueprint of how to be in middle age, Arrowby is an example of how not to be. 

Middle England by Jonathan Coe (2018)

The final instalment of Jonathan Coe’s sweeping trilogy continues the multi-generational tale of the British families he introduced in The Rotters’ Club and The Closed Circle – now against the backdrop of Brexit referendum-era Britain.

Not just a clever, incisive interrogation of contemporary British identity (though it is, undoubtedly, that), Middle England is also a meditation on family relationships, and the ways that politics, class and identity come to bear on them over timespans short and long.

It’s a mature, eye-opening novel that asks big questions about the beliefs we too often let calcify over time.

Inheritance from Mother by Minae Mizumura (2017)

Set in a tradition-stifled Tokyo, 50-something French teacher Mitsuki grapples with a husband who's having an affair with a much younger woman and an old mum who won't die. As per tradition in Japan, she's moved the frail old matriarch into her home to care for her until death. Which can't come soon enough, as far as Mitsuki is concerned.

Far from the demure, self-sacrificing paragon of Japanese cliché, her mother is a self-absorbed battleaxe who makes Mitsuki's life hell. Still, Mitsuki does all she can to ensure the old lady's happiness, while guiltily dreaming of the day she will be set free to finally enjoy her middle age.

As the novel progresses, we are offered deep insights into the many paradoxes of Japanese culture – a fast-changing ultra-modern society framed by rigidly traditional values. That, and a profound study on the complex relationships of mothers and daughters, ageing and the strength of women.

Something Happened by Joseph Heller (1974)

Most of these books offer some sort of wisdom about enjoying your 50s. About taking middle-age by the horns and flipping the finger at time. Joseph Heller's story of a man ground into the mud by life has none of that. In fact, it's so punishingly bleak it might be better seen, in the context of this list, as a literary crash kit to jumpstart any fading joy for life, rather than inspire it.

It's so depressing, in fact, Kurt Vonnegut, in his now famous review in The New York Times, once asked: "Is this book any good? Yes. It is splendidly put together and hypnotic to read... one of the unhappiest books ever written.”

On paper Bob Slocum has it all. He's a white, privileged and reasonably successful ad-man; a war vet with a beautiful wife and three lovely children. And yet, he's also a serial philanderer, a closeted boozer, wants a divorce and to quit his job. He doesn't know why he's like this, only that, “Something must have happened to me sometime.” But rather than pulling his finger out, he spends his days wondering why bad things happen to good people... until, one day, something bad actually happens.

As you'd expect from the author of Catch-22, it is funny, astute and, as the LA Review of Books put it, "one of the most pleasurable, engrossing, and in retrospect moving American novels ever written.” 

The Brotherhood of the Grape by John Fante (1977)

Henry Molise is a 50-year-old writer who returns to his family home to help his ageing parents work out their late-life divorce. When he arrives, in a sudden pang of filial piety, he agrees to help his tough-as-nails dad build an outhouse in the hills.

Trouble is, his alcoholic dad was a mean old crank to Henry growing up, squashing his dreams of becoming a baseball player to stay under his control as an apprentice stonemason.

Soon, some of his dad's drinking pals tag along – the brotherhood of the grape, whose credo is, portentously, “it's better to die of drink than to die of thirst”. But, as they descend deeper down the bottle, undead resentments break through the soil; they fight, make up, fight some more, and learn some home truths along the way. The lesson? Leave hard boozing to young men in their twenties. It sure as old boots won't help you 30 years down the line.

Death in Venice by Thomas Mann (1912)

Death in Venice is one of the great classics of European literature, a compassionate tale of the death of youth... with a valuable lesson to boot. Gustav von Aschenbach is a successful writer in his 50s with a terrible case of writer's block. So he travels to Venice in search of spiritual release.

But when he gets there, he doesn't find inspiration in the beauty of the city, rather in the crushing beauty of a 14-year-old boy. He never speaks to the boy, let alone touches him, rather he observes him from a creepy distance – falling deeper in love as each day goes by. He stalks him about, and watches him on the beach, and from there he descends into full-blown obsession. He even visits a barber to dye his hair and rouge his face to give him a younger look.

This is not a story that can, in any way, end well for Gustav. If there is a moral in this tragic tale of mortality, infatuation and forbidden desire, it is that Gustav's obsession with the boy is really a reflection of his obsession with his own loss of youth.

Disgrace by J M Coetzee (1999)

The novel that won South African writer J M Coetzee both the Booker Prize in 1999 and the Nobel Prize for Literature in 2003 has seemed more relevant than ever in recent years. Following the professional and personal decline of David Lurie, an aging English professor in Cape Town who has an affair with a younger student, it explores exactly the kind of abuse of power which typfied stories that emerged from the #MeToo movement.

The other great theme of this masterful novel is racial tension and the legacy of apartheid in South Africa. But for the purposes of this list we might focus on what Disgrace has to tell us about middle age, and the pitfalls it presents. Lurie fits almost perfectly into a stereotype that has gained real momentum in recent years – partially fuelled by grumpy exchanges on Twitter – that of the man of advancing years whose ears are closed to anyone's tastes or opinions other than his own. Throughout the novel, Lurie variously 'mansplains' Mozart, Byron and how his daughter should respond to being sexually assualted. If the trick of growing old is to do so gracefully, David Lurie is perhaps a cautionary tale about doing the opposite. 

Rabbit is Rich by John Updike (1981)

Much of John Updike's work has been unfavourably reassessed in recent times: to put it mildly, his sexual politics have not aged well. Nevertheless, few would contend that when he was good, Updike was sensational. This installement in his most famous series, following the one-time high school basketball star Harry "Rabbit" Angstrom, won him the Pulitzer Prize for Fiction in 1982 and holds up as well as any of his famously prolific output.

In Rabbit is Rich we join Angstrom in 1979 at the peak of his professional game managing a Toyota dealership. He's financially secure for the first time in his life, his turblent marriage to Janice is relatively stable and his son Nelson is in college. In other words, everything is perfectly primed to go wrong. 

The Rabbit series definitely got more interesting as its hero grew up – the next in the series, Rabbit at Rest, won Updike his second Pulitzer – and Rich is full of the soaring and expansive prose style that marked his geniues. Angstrom is a fine companion through the trials and tribulations of late life, whether it's family, work or (of course) sex. 

What did you think of this article? Let us know at editor@penguinrandomhouse.co.uk for a chance to appear in our reader’s letter page.

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