Jane Urquhart
I have always felt the small, thin-skinned, male Pomeranian in Anton Chekhov's story The Lady with the Dog, and the motherly, very competent Newfoundland dog, Nana, from J.M. Barrie's Peter Pan, would have made a splendid love match. The over-indulged and inexplicably nameless Pomeranian is clearly the victim of numerous neuroses – especially after his much-loved Anna betrays him by taking him with her to Yalta only to transfer her affections to the married misogynist Gurov – and would, therefore, benefit from Nana's peculiar variety of no-nonsense loyalty.
In the first fine flush of the affair, Nana might sympathize with the tearful Pomeranian's adolescent whining about the fact that after he growled at Gurov, he was summarily and completely dismissed from Chekhov's plot. But as time passed and their affection calmed and deepened, I expect that Nana would have knocked the Peter Pan syndrome right out of him with a combination of warmth and "old-fashioned remedies like rhubarb leaf."
Jane Urquhart's 20-year-old novel Away is the official selection representing the region of Ontario in CBC's 2013 Canada Reads, Turf Wars.
Eleanor Wachtel
I'd like to show Emma Bovary a good time – especially on Valentine's Day. I know she often seems bored, discontented, aspiring, envious, extravagant and romantically deluded, but she deserves better than the grotesquely painful death by rat poison that Flaubert delivers in such detail. After all, many of her fantasies are derived from reading novels, so who – except Dante – can blame her for that? She's beautiful, convent-educated, well-dressed and ambitious. The problem is finding the right romantic man. Most 20th-century heroes are anguished anti-heroes, sympathetic but closer to Hamlet than Heathcliffe. And I do think Emma needs a man from a later, less conventional era.
So I'm sending her on a date with The English Patient, Count Almasy, during his dashing, adventurous days as a desert explorer and pilot, before the Second World War. She'd love the royalty, even if it's Hungarian. He's charming, poetic and tough – there's always a slight frisson of violence in Michael Ondaatje's love scenes – but also determined and passionate. He and Emma together in Cairo in the 1930s, dancing, drinking, partying and living dangerously. You might think, with his Herodotus, that he was too scholarly for her, but he does say: "I am a man who did not enjoy poetry until I heard a woman recite it." In the desert moonlight, of course. They even have the moral ambiguity of their actions in common.
We know it will end in tears, flame out – literally – but this is before, when Emma has at least a degree of agency and a Valentine.
Eleanor Wachtel is the host of CBC Radio's Writers & Company and Wachtel on the Arts. Her most recent books are Original Minds and Random Illuminations.
Andrew Pyper
Frankenstein's Monster and Anne Shirley. The monster in Frankenstein (the articulate one from Mary Shelley's novel, not the grunting shuffler from the movies) is a frightening creation, a gruesome assembly of stolen parts, but he's also heartbreakingly lonely. I've always wished for him what he wished for himself: female companionship, or at the very least, a naughty weekend of undead whoopie. But who would be a good match for an abomination of science with no name and serious daddy issues? How about our own Anne Shirley? She's an orphan too, after all, and so might better sympathize with the monster's plight. And as an unstoppable chatterbox, she could undoubtedly banter about mortality and the torment of existence with a self-loathing murderer for many pleasant hours. "My life is a perfect graveyard of buried hopes," Anne quotes, with understanding, in Anne of Green Gables. Well, who knows buried hopes – and graveyards – better than Shelley's creature?
Andrew Pyper's new novel, The Demonologist, will be published in March.
Alissa York
White Fang and Black Beauty. The world adores a story of star-crossed lovers, so long as the happy couple die in the end. But what if a pair of true survivors – a half-breed bush-fighter and a thoroughbred fallen on hard times – were to fall in love across enemy lines?
Even if they weren't natural foes, White Fang and Black Beauty would seem to make an unlikely match. But are they so very unalike? Both know what it means to be broken. Tethered then caged, White Fang was made over into a blood-sport champion and repeatedly beaten to the brink of death. Black Beauty bore the weight of hateful riders and the misery of a filthy stall; reduced to a beast of burden, he worked under the lash to the point of total collapse. Even when they found happy-ending homes, both remained the property of their owners, at risk of being bought and sold.
It's not the stars that cross the bravest of our lovers, it's us – humanity at its lowest, concerned not with love but with control. So to hell with the masters, be they cruel or relatively kind. Let our improbable valentines live. Let the grey bruiser gnaw through his leash while the dark-eyed gent kicks down his stable door. Let them meet up by moonlight in the back paddock, leap the last fence and run.
Alissa York's most recent novel is Fauna, in which the characters tend to be either animals or animal-lovers.
Mark Kingwell
Sebastian Flyte, from Evelyn Waugh's Brideshead Revisited, should marry Lily Bart, the doomed heroine of Edith Wharton's The House of Mirth – the place, according to Ecclesiastes, where dwell the hearts of fools. Lily is no fool, really, just a too-beautiful and not-rich girl approaching 30, overfond of nice clothes, gambling and male attention, and bored silly by the eligible, wealthy, Americana-collecting bachelor-dullard who looks like her best bet for social respectability. Her intellectual match, the young lawyer Lawrence Selden, is too poor himself and, frankly, too feckless to bust a real romantic move on her, until it is (just) too late. Dolt. Lily dies with her financial ledger balanced but her heart's vault empty.
I know what you're thinking: But Sebastian is a tortured alcoholic gay Catholic, a sinner in love with misery. Yet, when the two meet at a society party in London, he is not too drunk to see that smart, lovely Lily will be the perfect beard for the mariage blanc of his dreams, where the country-house parties will always include new gowns for her and gin and Germans for him. They will both get exactly what they want out of life, and their performance of conjugal conformity will satisfy even Lady Marchmain, Sebastian's passive-aggressive mother. Eventually, they will inherit Brideshead itself. Yes, that will entail the early, heirless death of Sebastian's priggish older brother, Bridey, but nobody is likely to consider that any great loss.
Mark Kingwell's latest book is the essay collection Unruly Voices : Essays on Democracy, Civility and the Human Imagination. He teaches philosophy at the University of Toronto.
Cathy Marie Buchanan
Wouldn't Little Women's Jo March make an ideal partner for To Kill a Mockingbird's Atticus Finch? She'd like his stillness and courage and sense of fairness, his quiet pondering. Their politics are aligned. She shows a clear preference for men in middle age. And doesn't Atticus deserve a break? He's widowed. Half of Maycomb is against him. He's got two kids under the age of 12. He works awfully hard. Jo could bring the bit of frivolity missing from his life. Sombre Atticus's face would regularly break into a smile, and the ladies of Maycomb would get some badly needed Virginia Woolf, and Scout would get a tomboy mother, a kindred spirit. Haven't we all had enough of Aunt Alexandra and her frilly-dress aspirations for her coverall-loving niece?
Most of all, though, at the close of Little Women, when Jo weds a German professor, something is terribly amiss. Hadn't she professed aspirations to be a writer all along? Hadn't she moved to New York and taken up the quill with enough verve to support herself, and to send Beth and Marmee to the seashore? In Chapter 42, we learn Jo has long last found her writerly style! Why, then, does she end up with a German professor, turning an old house into a school? She should be in Maycomb, living her dream, with Atticus Finch.
Cathy Marie Buchanan's most recent novel is The Painted Girls.
Robert Sawyer
For Valentine's Day, I propose the pairing of two wonderfully righteous men: Atticus Finch from my favourite novel, Harper Lee's To Kill a Mockingbird, and the world's greatest consulting detective, Sherlock Holmes, who I suspect was 221B-curious. Yes, some would have labelled their romance A Scandal in Alabama, but to me, it's To Kiss a Baker Streeter. Both men, of course, were towering intellects; both laboured for the cause of justice, and both often came to the aid of those who had no one else to help them. Though neither was demonstrative – the only endearment Atticus might ever have heard would have been the occasional "Elementary, my dear Finch" – each was passionate in his own way, and they'd have made a truly handsome couple.
Robert J. Sawyer's science-fiction/mystery Red Planet Blues comes out in April.
Joe Queenan
King Lear and Père Goriot would make a nice pair. Horrible daughters in each case. Worked themselves into the ground, and for what? Bet those two would have some great stories to share. They always say there's no fool like an old fool. Well, how about two old fools. And remember: Lear opted for voluntary early retirement. Bad, bad, bad idea.
Joe Queenan's most recent book is One for the Books.
George Elliott Clarke
In Shakespeare's eponymous tragedy, Othello, the "Moor of Venice" and governor of Cyprus, is tricked into believing his white wife, Desdemona, had been unfaithful, suffocates her and then, realizing his error, commits suicide. How much sweeter life would have been had Othello been paired with O, the heroine of Dominique Aury's novel, Histoire d'O, which relates the adult fairy tale of a woman who so loves her man that she submits to his decision to allow others to violate her, willy-nilly. Othello would have found O so obedient that she'd cuckold him only if he commanded it.
George Elliott Clarke is the poet laureate of Toronto. His most recent book is Red.
Maile Meloy
The literary matchup I want to see most is Stephen Maturin – the cranky, brilliant physician and naturalist and spy from the Patrick O'Brian novels – and me. I know it could never work, as I'm not a fictional character, so I've tried to come up with someone else for him. Isabel Archer would be game and adventurous enough, but after the conniving Gilbert Osmond she might want someone open and cheerful – Jack Aubrey from the O'Brian novels, not his pinched and secretive friend.
Dr. Maturin would admire Anna Karenina's spirit, but he isn't handsome or dashing enough to keep her from her train. Lizzy Bennet lives conveniently at the right time, but she would never give up Mr. Darcy's magnificent Pemberley for Stephen's ruined castle in Spain. Who else would put up with midnight autopsies on the dining room table, and crates of preserved specimens, and the occasional pet sloth, and would love and treasure him anyway? Who but me?
Maile Meloy's most recent novel for adults is Both Ways is the Only Way I Want It.