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Stuart Simpson/Penguin

For most people, your twenties is the decade you learn how to be an adult, having your first serious relationships, taking your first careers step and learning your first difficult lessons about yourself and the world. Naturally, all this stuff is reflected in great literature.

Giovanni's Room by James Baldwin (1956)
'You don’t have a home until you leave it and then, when you have left it, you never can go back.' So goes some advice to protagonist David in this soaring classic of gay literature, about a young American man coming to terms with his sexuality through a tortured love affair with an Italian barman in Paris.

It's not just that Baldwin's writing is knock-you-sideways gorgeous at all times, which it is. It's also that Giovanni's Room grabs you by the heart and squeezes with a strength few books can muster. It blows open ideas about lust and desire, love and loyalty, but it is also about growing up, losing innocence and accepting who we are for ourselves. We may be the sum of our choices, but we are the sum of our changes, too. Home, in other words, is who we are, not where we're from.

The Picture of Dorian Gray by Oscar Wilde (1890)

This is the tale that never grows old. When naïve young Dorian is introduced to a fashionable society painter, the artist is compelled to paint his portrait. So overcome by the result's beauty is Dorian, that he declares he'd give anything to look like that forever. His wish is granted, but there's a catch: while his looks will remain unblemished by time, the portrait will suck up all the awful energy of his ugly character.

Dorian soon spirals into a high-society world of drugs, debauchery and, ultimately, soulless despair until, in a terrible climax, he tries to destroy the painting with disastrous consequences. It is, in effect, a powerful reminder that youthful looks aren't everything; substance is important, too; a terrible vision of the corrupting influences of self-delusion. The message: it's better to accept yourself, flaws and all, than to drown them in denial. Beauty, in other words, comes from within.

Fates and Furies by Lauren Groff (2015)

Fate and Furies was the most talked-about novel of 2015 – a word-of-mouth sensation that even landed on the bedside table of Barack Obama, who chose it as one of his favourite books of the year.

So, it's a marriage seen from two sides. The first half ('Fates') is the husband's perspective. For him, things are fine, mostly happy, quite complacent. The second is the wife's ('Furies'). For her, things aren't great at all.

It is a masterful exploration of how living with each other, side by side doesn't necessarily mean knowing each other, inside out. Or, as the American critic Laura Miller wrote, 'They are at that point in life when they realise that a wedding is less the end of a fairytale than the beginning of a mystery, and sometimes an ugly one.' It is by no means the first marriage-under-the-microscope novel, but it is so clever and insightful that it's easy to feel like it is.

Bridget Jones' Diary by Helen Fielding (1996)

 

Ultimately Bridget Jones' Diary is the perfect antidote to that feeling we all get at some point in our life, especially early on: that we're not quite good enough. As Helen Fielding wrote of the book's success in 2013, 'I suspected that what Bridget had unwittingly tapped into was the gap between how people feel they are expected to be on the outside and how they actually feel inside.' It's also absolutely hilarious.

Anna Karenina by Leo Tolstoy (1878)

This is the ultimate writers novel, said by many to be the greatest work of literature ever written. It is about a beautiful and rich noblewoman who seems to have everything, yet is unsatisfied. Until, that is, a handsome army officer sweeps her off her feet. Their affair scandalises Russian high society, as well as her family, unleashing a wave of bitterness and jealousy.

With its vast cast of characters, Anna Karenina is a spinning phantasmagoria of human life, covering themes from love and desire to destiny and death, family conflict and the inexorable contradictions of fate. But ultimately, it invites us to think about what makes relationships work, placing mutual respect and compromise above the raw power of love alone. As Tolstoy writes: 'I've always loved you, and when you love someone, you love the whole person, just as he or she is, and not as you would like them to be.'

The Great Gatsby by F Scott Fitzgerald (1925)

This American classic contains possibly the greatest – and most brutal – line anywhere in literature about the grating fear of leaving your twenties. 'I was thirty,' groans protagonist Nick on his birthday, 'Before me stretched the portentous menacing round of a new decade … Thirty – the promise of a decade of loneliness, a thinning list of single men to know, a thinning brief-case of enthusiasm, thinning hair.'

It's a line that should resonate with anyone who's beaten on in that same boat, clinging stubbornly to a past of which they know they must let go. But The Great Gatsby is not a bleak indictment of the slow creak towards death. There is hope for Nick, and he learns many valuable lessons about growing up and getting to grips with oneself during that summer with Gatsby and pals. 'I'm thirty,' he says in the final chapter, 'I'm five years too old to lie to myself and call it honor.'

The Alchemist by Paolo Coelho (1988)

'Everyone seems to have a clear idea of how other people should lead their lives, but none about his or her own.' So says Coelho in The Alchemist. And there is something alchemical about Paolo Coelho's writing, like the warm hand of a wise uncle, or life guru, resting tenderly on your shoulder. He's written many books, to mostly glowing critical acclaim, but The Alchemist has to be his best. It is, ultimately, about listening to your heart, following your dreams and grabbing opportunities as they whiz past your face.

It follows a Spanish shepherd boy who leaves home for Egypt in search of buried treasure. Along the way he encounters a string of colourful characters, and no shortage of roadblocks. But he soon discovers that, as well as the real treasure in the desert, there as another he must find – the one inside his soul. All in, it is a book about what it takes for some to conquer their fears and chase their dreams, and why others buckle under the crushing weight of human existence to just... exist.

The Reluctant Fundamentalist by Mohsin Hamid (2007)

About race and identity in post-9/11 world, this Booker-shortlisted novel follows a starry-eyed college student from Pakistan who makes a new life in America. Only, after a disastrous love affair followed by the World Trade Center attacks, he is thrown into a tumble drier of racism and unfounded animosity, until he comes out shrunken by disenchantment with the capitalist dream. Years later, he's in Lahore, telling an American how the event changed his life.

The Reluctant Fundamentalist is a transformative book for anyone in a tussle with identity and ideology within the ever-shifting matrix of global politics, plus a useful lesson in the paradox of control: the more we try to master what happens in our lives, the harder it gets. But it's also a thought-provoking exploration of the concept of prejudice, and how it infects our world, a subject as relevant now as it was then.

The Secret History by Donna Tartt (1992)

This multimillion bestseller was described by The New York Times as a combination of Dostoyevsky, Euripides, Easton Ellis and Waugh. In essence, it is a modern Greek tragedy about a close-knit bunch of 20-something classics students coming to terms with their lives and choices.

The narrator, Richard, is looking back on his life and what led to the killing of one of his friendship group. Joining an elite college in Vermont, his rich, snobbish schoolmates reflect the shame he has for his blue-collar background, so he invents an upper-crust identity to impress his new mates. As time wears on, the group's dynamic is rocked by a series of dark incidents.

Tartt's voice is seductively ruminative in The Secret History, carrying the reader through a dark world of lies, addiction and emotional manipulation. It is, boiled down, a book about secrets and relationships and how the two do business.

The Amazing Adventures of Kavalier & Clay by Michael Chabon (2000)

We all wish, or have wished, for our own superhero transformation. In The Amazing Adventures of Kavalier & Clay, the Pulitzer Prize winner for fiction in 2001, we have a chance to dream. It follows a young artist called Josef Kavalier and his Brooklyn-born cousin Sammy Clay in the years following Kavalier's escape from Nazi-ruled Poland in the 1930s. Kavalier joins Clay in New York during the Golden Age of comic books where they work together at a magazine. Together they invent a superhero called The Escapist, 'whose power would be that of impossible and perpetual escape'.

It is a towering Everest of a novel about ingenuity and heartbreak, the search for identity, the very-human need to escape (family expectations, social constraints, oppression etc.), loves lost and found, and the growing up we all do in our 20s and early 30s, way after society calls us 'adults'.

Fear of Flying by Erica Jong (1973)

This was the book that, more than any other of its time, changed the way the western world thought, and talked, about sex. It follows a young female erotic poet called Isadora Wing who, bored with her second marriage, ditches her husband at a psychoanalysts' conference in Vienna to travel through Europe in search of herself, and great sex (so long as the latter comes with no strings). The only thing holding her back: a crippling fear of flying.

A big part of the push towards second wave feminism in 1970s, Jong's witty and quiveringly explicit account of Isadora's escapades, according to the New York Times, 'electrified and titillated the critical establishment.' John Updike called it 'fearless'. And Henry Miller said it would 'make literary history' for its 'wisdom about the eternal man-woman problem.' A soaring exploration of sex and self.

NW by Zadie Smith (2012)

‘I am the sole author of the dictionary that defines me,' says someone on the radio at the beginning of Zadie Smith's fourth novel. It raises a question mark that hangs over NW like a whispering ghost.

The story weaves in and out of the lives of four Londoners - Leah, Natalie, Felix and Nathan – as they navigate the choppy waters of life after they leave their childhood council estate in north-west London. Each have gone their separate ways, but a chance encounter brings them back together, forcing them to confront their choices, their pasts and who they're trying to be.

It is, in some ways a love letter to big-city living in all its beauty and brutality. But it's also about class, race and gender, and how attitudes to all three evolve. NW was, she has said, her attempt at writing the first 'black existential novel', that asks, to what extent, really, are we the 'sole authors' of our lives?

A Little Life by Hanya Yanagihara (2015)

This tender portrayal of a friendship group of college graduates who coalesce around one of the friends, haunted by the nightmare of his childhood. Yanagihara delicately weaves each young man's lives throughout her text with the lightest touch, such that the reader will fall in love not with any one character but with their selfless motivation to support each other in times of need. A Little Life is at once a jarring examination on the trauma of childhood abuse and a heart-lifting ode to the power and possibilities of adult male friendship.

In the hands of a less talented writer, the men's intense loyalty for each other might seem annoyingly unrealistic (are men really that selfless?), but Yanagihara pulls it off with a subversive brilliance that few writers have in their arsenal. The New Yorker breathlessly described it as a novel that will 'drive you mad, consume you and take over your life', while the Guardian called it called it ‘the perfect chronicle of our age of anxiety, providing all its attendant dramas ... as well as its solaces.'

Portrait of the Artist as a Young Man by James Joyce (1916)

This is James Joyce’s first novel, published when he was in his early thirties. It begins in the early childhood of its protagonist Stephen Dedalus and follows him as he grows into (you guessed it) a young man. Not only is the prose-style unique and gorgeous, but Dedalus’ journey through young adulthood remains as relevant now as when it was written.

As the celebrated Norwegian writer Karl Ove Knausgård put it in 2016, 'Portrait', simply, is about 'a young man’s soul.' But what makes Joyce’s novel so magical, according to the My Struggle author, is that 'his conquest of what belongs to the individual alone … is also a conquest of what belongs, and is unique, to each of us.' It's powerful stuff; vivid, beautiful and swelling with mood.

Supper Club by Lara Williams (2019)

One of 2019's biggest bestsellers, Supper Club could be seen as a feminist retort to Chuck Palahniuk’s Fight Club. Only, rather than use violence to quell their existential ennui, Williams' heroines use food.

Roberta, 29, has a boring job at a fashion website where she meets bisexual Stevie. They decide to launch a supper club for 'hungry women' who've been let down by men. As the group's numbers grow, so does the party – they gorge on food, dance, drink, do drugs, strip, have sex, vomit, and begin to break the law. They deliberately put on weight in a bid to become 'living art projects'. But it's not all fun and frivolity; there are serious messages, not least a stomach-churning thread about sexual abuse.

It is a powerful and original critique of women's oppression by men, but it's also supremely funny, uniquely smart and wincingly well-observed. And, in places, it's extremely moving. Will the club fill the void in Roberta's life? Or is that something she needs to find elsewhere?

Passing by Nella Larsen (1928)

About a mixed-race woman who spends her life 'passing' as white, Passing is a book that has been at the centre of racial identity discourse since it was written almost 100 years ago.

The story introduces two mixed-heritage friends who haven't seen each other in a while, but reunite in a Chicago hotel. Clare, Irene learns, has been living as a white woman with a racist husband who has no idea of his wife's background. Clare, on the other hand, remained in the African-American community but refuses to acknowledge the racism that holds back her family's happiness. They soon become consumed by the other's chosen path – until events conspire to force them confront their lies.

It is a book dripping with feeling, exploring issues around female racial identity in a way almost no other writer dared at the time.

Animals by Emma Jane Unsworth (2014)

Described by Caitlin Moran as ‘Withnail with girls’, this is about two early 30-something friends who love nothing more than a 3am bender – a tale of half-remembered parties, fallouts with drug dealers and fuzzy-mouthed hangovers. But then one decides to get married, forcing the jarring question: are your 30s time to reign in the partying, or can it carry on until the triumphant (or bitter) end?

On its publication Animals was praised to the literary rafters for it's bold, unflinching portrayal of female friendship and all the nuances contained therein. But it also asks questions about societal expectations of women, particularly: why are women's lives, and choices, scrutinised in a way that men's seldom are? 'I didn’t feel I was getting a chance to read stories about women that went against the grain,' Unsworth said last year. 'There was no recreational joy allowed with drugs or intoxication or in sex. Women who were having a lot of sex were always troubled. Someone in their family had to be dying or have a hole in their heart.'

On Chesil Beach by Ian McEwan (2006)

A moving tale of sexual discovery in young marriage, the fragility of young love and ultimately, about the difficult transition from childhood to adulthood, On Chesil Beach is a post-nuptial psychodrama that lingers like a sad song.

Set in July 1962, as Britain teetered on the brink of the Swinging Sixties, Edward and Florence, 22 and 23, are on honeymoon, about to lose their virginities. Only, each has a vastly different view on how it should go down. He is excited but nervous, she is terrified. Neither can tell the other how they really feel. So they sit there over dinner, silent. ‘Even when Edward and Florence were alone, a thousand unacknowledged rules still applied,' writes McEwan early on. 'It was precisely because they were adults that they did not do childish things.’

They are new to adulthood, and don't understand it. So to suppress their sexual anxieties, among other big emotions, they treat it like a game. And for that they must pay the price with their happiness.

Never Let Me Go by Kazuo Ishiguro (2005)

Time magazine named this novel, about unknown destiny, and staying sane in a world that forbids us from acting out our hopes and ambitions, as the best book of 2005, gushing, 'the book is a page turner and a heartbreaker, a tour de force of knotted tension and buried anguish.'

A 31-year-old looks back on her life at a boarding school that prepared her and her classmates for organ harvesting to maintain older generations. To go too deeply into the plot would be to spoil the heart-punching shocks (one in particular) that spring up throughout this masterpiece, one that helped win its author a Nobel Prize in Literature in 2017 for his ability to uncover the 'abyss beneath our illusory sense of connection with the world.'

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