Becky Sharp and Jay Gatsby
It goes without saying that the ambitious, calculating Becky Sharp would go for the mysterious millionaire Jay Gatsby in a heartbeat — all she would have to do would be to attend one of his glamourous parties and take a look around to know he was the richest man in the room. Gatsby himself would be swayed, like so many other men, by Becky’s considerable charms, but once together, the two of them would really fall in love over their mutual rise from nothing to the gilded peacocks they became at their respective peaks. Just don’t tell her too soon, Jay, or she’ll run like the wind. But perhaps without all that Daisy business no one would ever find out, so you’re probably in the clear.
Holden Caulfield and Esther Greenwood
If he could ever fall for anyone, the quintessential example of masculine teen angst would probably go for the classic example of feminine teen depression. After all, Esther’s condition is much like Holden’s, although, ahem, way less phony. The two of them could sit by the duck pond together, complaining about the oppressiveness of the world and their parents’ inabilities to fully understand them, and then maybe hold hands a little.
Arya Stark and Ender Wiggin
Though they come from very different worlds, we envision a young budding romance between the fearless, defiant tomboy Arya and Ender, the genius battle master with the weight of the world on his shoulders. Arya has enough of the fight in her to join Ender’s tactical team, but enough of the gentle lady to take the place of Valentine in his heart. In return, Ender would appeal to Arya’s adventurous side, and we bet she’d love to travel to different worlds with him to build new civilizations. As long as she could bring Needle.
Dorian Gray and Francis Abernathy
Though any match with Dorian is decidedly ill-advised, we know Francis would become enamored with the idea of the handsome young man and his Faustian pact — after all, Francis has his own interest with ancient magic, though his sensibilities are more Dionysian. This, in turn, would draw Dorian to Francis: a delicate, well-dressed gentleman who enjoys, with a group of his friends, hedonistic bacchanals in the woods. We think this match would almost definitely go up in flames in the end, but it would be pretty fantastic while it lasted.
Hermione Granger and Artemis Fowl
This pair of child geniuses would be immediately attracted to one another based on sheer intellectual prowess, probably launching into a technical conversation about fairy anatomy or rune translation within moments of meeting. There’s nothing better than that to get a kid genius’s motor running. Sure, Artemis is a criminal mastermind from a long line of lawbreakers and Hermione a goody-two-shoes lecturing about elf rights, but as everyone knows, the good girls always go for the bad boys. And maybe Hermione can melt that icy heart of his.
Tintin and Nausicaä
We’ve always thought that Tintin needed a woman in his life. Let’s face it: as it stands, the only female in his world is Bianca Castafiore, and we all know how appealing she is. We suggest Nausicaä, the princess of the Valley of the Wind, an adventurous, compassionate girl dedicated, much like Tintin himself, to the forces of good. Besides, we think Teto, Nausicaä’s pet fox-squirrel, would totally get along with Snowy.
Alexander Portnoy and Myrna Minkoff
Of course, Alex Portnoy needs a good Jewish girl to date. We were a little hesitant about suggesting that such a great character as Myra should go for the liver-abusing Alex, but we think “that minx,” a smart-as-a-whip New York City beatnik, might be able to show him what’s what, in more ways than one.
Willy Wonka and Mary Poppins
Let’s face it: Mary Poppins, the magical English nanny from all of our childhood dreams, is one of the most twee characters in the modern canon. Why wouldn’t she fall for a colorful man with a chocolate factory and a cohort of orange midgets? After all, if a spoonful of sugar helps the medicine go down, we bet a river of chocolate fudge would be an instant cure-all. Plus, they both favor the strangely-sized bow tie as a fashion accessory — and that’s definitely something you can pin a relationship on.
Jo March and Rhett Butler
For a girl who chided her sister on her romantic choice by scoffing, “He’s dull as powder, Meg. Can’t you at least marry someone amusing?” we suggest the witty, charming, swoon-worthy Rhett Butler. After all, doesn’t wonderful, literary, hot-tempered Jo deserve more than the Professor, himself rather dusty? We think so. Rhett is the black sheep of his society the way Jo is of her family, and the two would make a rebellious, exciting pair. At the same time, Jo would welcome Rhett, disowned by his own parents, into the March family, giving him more parents and sisters than he could ever want.
Emma Bovary and Hamlet
All we can say is, if Madame Bovary is looking for high position and an escape from her boring provincial life, then Prince Hamlet of Bloody Denmark is the man for her. Sure, Hamlet’s crazy, but he’s a Prince, so Emma’s hooked. Given her penchant for ignoring anything below the surface, we think she’d cruise happily through all the intrigue and falseness of Hamlet’s royal court, none the wiser. And as for Hamlet himself, after that Ophelia chick, Emma’s normal brand of crazy might come as a welcome relief.