From Sittenfeld to Soucy, Tolstoy to DH Lawrence: the love stories that end in disappointment or sadness can also be the most rewarding and haunting

As Tolstoy said: “All happy families are alike; each unhappy family is unhappy in its own way.” Is this true of romance too? Is a happy romance a cliche? Is a mess more familiar to us?

Readers are witnesses to the unseen motives, fears, and fantasies of characters. A book that switches point of view grants the reader a unique perspective of the relationships in the story, an angle the characters will never see. The reader understands what was at stake, what could have been avoided, what the other one was thinking. Readers are let in on a secret, and the secret becomes very complex.

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These complexities of loss and romance are ones I thought about when writing Paulina & Fran. What is romance? Can you have it with a friend? Is it always linked to sex? Does it truly ever die? Or does it just shrink and hide, then glimmer from its hiding place, like glitter stuck in the slats of your floor?

Here are 10 books I loved reading, and all contain a failed connection. I’ve kept my list mostly obscure (to intrigue you), and the descriptions as vague as I can, so as not to keep the plots of these worthwhile reads surprising.

1. I Am Elijah Thrush by James Purdy

This masterpiece of broken and odd love triangles involves two elderly enemies in a decades-long feud, an amateur memoirist, a flesh-eating animal, and a small boy who speaks in bird sounds. Each character has their own unusual, impossible passion. Purdy’s heartbreaking and scandalous tale begins with my favourite first line of any book: “Millicent De Frayne, who was young in 1913, the sole possessor of an immense oil fortune, languished of an incurable ailment, her wilful, hopeless love for Elijah Thrush, ‘the mime, poet, painter of art nouveau’, who, after ruining the lives of countless men and women, was finally himself in love, ‘incorrectly, if not indecently’, with his great-grandson.” Though this story is very amusing, the characters are in an almost constant state of wanting. They have much anxiety, pain, and sorrow over their love. Love is a cruel torture in this book. Moments of joy, surprise, accomplishment, and friendship, ease the mood but do not erase the pain.

2. Prep by Curtis Sittenfeld

Young love strikes two prep school students in such a real-feeling and exciting way, I read straight through a whole weekend until the inevitable turn. This skilfully told portrayal of first heartbreak made me empathise, agonise and occasionally admonish the painfully self-conscious protagonist, Lee. Painful moments of misunderstanding during Lee’s parents’ visit to the prep school where this story takes place made me cry, and other moments of inaction made me wish it were a choose-your-own adventure story, so I could guide Lee around.

3. Women in Love by DH Lawrence

This brilliant, thorough novel chronicles multiple romances from multiple viewpoints. Some flourish while others find cruel and violent ends. Lawrence writes from inside the relationships, voicing the duelling minds and conflicting thoughts, exposing the emotional dance at the heart of every romance. Written in 1920, parts of this book feel very modern to me – Gudrun’s fashion and some of the dialogue (“dunno”). In a book of this scope, there is room to explore everything, and DH takes his time describing a mining company, a dying father, a jealous girlfriend, a drowning child, a bleeding horse, an intellectual sculptor, a precocious child, a pregnant flirt, and countless others. My favourite scene is one that flashes between love and anger on a dirt road after a bad drive.

4. Desperate Characters by Paula Fox

This witty, exquisitely written story of daily life in 1970s Brooklyn is filled with vivid characters and examines the somewhat troubled and unsatisfying relationship of a married, childless couple. One of my favourite parts is the backstory of an affair between the main character and a publisher of plant books. A cat scratches the protagonist early on in the story and the suspense will make you late for your appointments. Paula Fox’s writing reminds me of Joy Williams and Flannery O’Connor. Her world is nuanced and unforgiving. Fox talks about people and ideas, fluently, gracefully, culling deep meaning from the everyday.

5. The Little Girl Who Was Too Fond of Matches by Gaétan Soucy

All is tragic in this insane and powerful novel translated from the French about eccentric, unsocialised children living in the aftermath of their father’s death. Love is so fleeting in this violently surprising story that one puts the book down in defeat, sighs, then must continue on, like the hero. I read the book in its entirety on a flight back from Spain, and on finishing it, was so awed and struck that I flipped to the beginning and started again.

6. The First Bad Man by Miranda July

Unlikely pairings are the most exciting. July is a master of the limitless ways two people can connect. Witness a relationship shift and mutate in this freewheeling, hilarious adventure of the heart. A must-read for anyone who loved July’s hilarious debut collection No One Belongs Here More Than You, or any numb reader in need of some laughter or wonder.

Facebook Twitter Pinterest Miranda July. Photograph: Todd Cole/The Wheeler Centre

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7. Anna Karenina by Leo Tolstoy

The ultimate book of tragic love: a married woman falls for a young officer and their troubled passion turns pages like the book’s on fire. This classic has three or four main threads, and like the DH, really captures life in a distant time and place. I admittedly skimmed some of the passages on farming to get back to these helpless love junkies, whose doomed relationship is startlingly well-written. At one point, Tolstoy so perfectly describes a young woman feeling pretty, I concluded he, too, was once a young woman.

8. Lucinella by Lore Segal

This meta-novella is a love letter to writing. Early on, the protagonist, Lucinella, meets a poet, but finds him lacking: “What I cannot forgive is the meagerness of the back of William’s neck.” My favourite aspect of this book is that Segal creates older and younger versions of Lucinella and puts them in scenes with Lucinella. So Lucinella must watch William flirt with young Lucinella, and Lucinella must see her future observing old Lucinella. Segal’s wild narration explores disappointment and ambivalence in love in frank, charming, and innovative ways, such as Lucinella watching her ex mourn her from the grave.

9. After Claude by Iris Owens

The protagonist of this hilarious and bizarre book is hating on Claude and his “dark, intense frog eyes” from page one, yet their interactions continue. She declares: “I am essentially a lighthearted person who tries to see the humour in the freak show called life.” Follow her unusual endeavours that lead her into a stranger’s apartment. This book runs on frustration, insults and weirdly beautiful lines that creep by when you least expect them.

10. Bad Sex by Clancy Martin

This dark novella drags the reader through a whirlwind of infatuation, sacrifice, lying, lusting, drinking, crying and nearly dying. In the opening chapter, Brett sleeps with her husband’s banker and her life is never the same. The dialogue and details are so real, at times it felt like a scandalous email from a troubled friend. The sentences are sparse. Not a word out of place. See the tropics and feel the feelings, vicariously, without the hangover.