Columns > Published on February 14th, 2023

9 Dates From Literary Hell

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Swooning over fictional characters is one of the perks of being a bookworm. They’re dashing and charismatic, romantic and audacious. But there’s also the characters we’d never want to run into in real life. Sometimes they’re the villains, sometimes they’re the unlikeable protagonists, and sometimes they’re side characters whose toxic traits take up the entire page. They lie, cheat, and manipulate, preferring obsession and control over respect and trust. Here are nine fictional characters that would be absolute dates from hell.

Joe Goldberg — "You" by Caroline Kepnes

When aspiring writer Guinevere Beck comes into Joe Goldberg’s bookstore, he knows she’s the one—literally. No one else in New York has her name, making her vibrant and prolific social media easy to find and Beck even easier to follow. All he needs is to create the perfect encounter. As he moves from the sidelines of Beck’s life to her boyfriend, Joe transforms himself into Beck’s perfect man. And he’ll do anything to stay there.

We all like attention, but Joe takes things from flattering to downright terrifying. Even though Joe is probably really good at making date night feel special, the charm quickly wears off once his true motives shine through.

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Ayoola — "My Sister, The Serial Killer" by Oyinkan Braithwaite

Whenever Korende’s sister Ayoola breaks up with a boyfriend, things tend to get messy. Bleach, gloves, and an iron stomach kind of messy. After Ayoola kills her third boyfriend, Korende knows she should go to the police, but she loves her sister. Until Ayoola starts dating the doctor Korende works for as a nurse—and is in love with. To save one, Korende condemns the other, putting her loyalty to the ultimate test.

Obviously, winding up dead is a less than ideal end to a date. And Ayoola would rather commit murder than do the whole it’s-not-you-it’s-me thing. Break ups are never fun, but there are a million better ways to handle these uncomfortable conversations than becoming a serial killer.

Get My Sister, The Serial Killer at Bookshop or Amazon


Zoe Cross — "Things Have Gotten Worse Since We Last Spoke" by Eric LaRocca

The last thing Agnes Petrella expects when she reluctantly posts her antique apple peeler for sale in an online forum is to meet someone who truly sees her. As her relationship with Zoe develops, Agnes finds herself becoming more confident and self-assured. But when mutual admiration turns into something darker, the line between desire, destruction, and depravity gets blurred. 

Online dating is always tricky. Are you being catfished? Scammed? Or is the person on the other side of the internet, actually genuine and real? All we can say is, if you’re going to connect with someone online, run far away if they ask you what you’ve done to deserve your eyes.

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Calamity Ganon — "Sign Here" by Claudia Lux

Peyote Trip worked hard to make it all the way to the deals department on the fifth floor of Hell. Nothing ever works, disaster always strikes, and Jäger is the only drink on tap. But Pey has a plan. He just needs one more member of the Harrison family to sell their soul. And their summer vacation at their family lake house might be the perfect opportunity to get it. But as Pey works his plan, secrets on all sides threaten to unravel a millennium of planning. Because it doesn’t matter whether you live in Hell or on Earth, every choice has a consequence.

Calamity Ganon might be an interesting person, but if Jäger is the only option, the date is going to be pretty terrible. Add on lies, manipulations, and ulterior motives, and you are pretty much guaranteed a date from hell in Hell.

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Tyler Durden — "Fight Club" by Chuck Palahniuk

When an unnamed narrator can’t find relief from his crippling insomnia, he turns to support groups to help him. It’s only after he pretends to be seriously ill in those groups that he finds sleep. He meets the mysterious Tyler Durden on a business trip, who convinces him to leave support groups and start an underground fight club as an unconventional—and radical—therapy. But things with Tyler are far more complicated than he ever imagined. And fight club is only the beginning.

Marla Singer may not be what anyone would call a good person, but even she doesn’t deserve the mind games Tyler plays with her. Maybe he raises some valid points about consumerism, but his chaotic personality and violent philosophy is nothing but a giant red flag.

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Gregory — "Untamed Shore" by Silvia Moreno-Garcia

Viridiana is bored in her small fishing town in 1979 Baja, California. She dreams of Hollywood, where romance and adventure might fill her future instead of marriage and children. After three wealthy tourists arrive from America, she quickly becomes enamored in their exciting, glamorous lives. But when one of them dies, Viridiana lies to help her new friends only to find herself tangled in a complicated web of secrets and lies. 

Smooth-talking Gregory might seem charismatic and charming on the surface, but his selfish nature can’t help but shine through in everything he does. We all have secrets about our past, but sometimes if things are too good to be true, they are.

Get Untamed Shore at Bookshop or Amazon


Jay Gatsby — "The Great Gatsby" by F. Scott Fitzgerald

Everyone knows Jay Gatsby. Or of him, anyway. His mansion is constantly brimming with the young and the rich, all capitalizing on Gatsby’s generous parties that never seem to end. Nick Carraway somehow finds himself friends with the enigmatic Gatsby, who convinces him to arrange a meeting with Nick’s cousin, Daisy Buchanan, to reconnect their shared past. But sometimes memories are best kept buried. Unfulfilled desire, secrets, and obsession all threaten the glittering life he’s spent decades building.

A relationship built on lies is never ideal, but Jay Gatsby takes that to the extreme. Rather than admitting that Daisy might not be the right person for him, he simply decides to live a whole new life, paid for by questionable activities, to seduce a married woman away from her family. Not a great look, to be honest.

Get The Great Gatsby at Bookshop or Amazon


Christian Grey — "Fifty Shades of Grey" by E.L. James

When Anastasia Steele first sees Christian Grey, she’s shocked that her first reaction is desire. He’s smart but intimidating, and Ana finds herself desperate to be near him. Grey has his own desires, and they’re far more erotic than Ana is used to. As their physical affair grows more passionate, Ana discovers Grey’s secrets while exploring her own dark urges. But Grey has inner demons tormenting him, threatening to unravel their relationship by his desperate need for control.

The warning signs for this guy are practically flashing neon red lights. Christian Grey might be rich and sexy, but anyone who would rather dominate and control their romantic interests rather than treating them like an equal is the very definition of a date from hell, in our opinion.

Get Fifty Shades of Grey at Bookshop or Amazon


Amy Dunne — "Gone Girl" by Gillian Flynn

The last Nick Dunne expects on the morning of his fifth wedding anniversary is for his wife to disappear. As police investigate, Amy’s friends reveal that she was terrified of Nick, his computer has strange searches, a strange number keeps calling his phone, and the police keep finding secrets that Amy hid from Nick. He insists he’s innocent. But Amy is still missing. And he’s the primary suspect.

Amy Dunne is a woman with more than just a plan. She has plans within plans, thought out years in advance with chilling calculation. We’re all for being organized, but this level of premeditation is a bit extreme for our taste.

Get Gone Girl at Bookshop or Amazon


About the author

Jena Brown grew up playing make-believe in the Nevada desert, where her love for skeletons and harsh landscapes solidified. A freelance writer, she currently contributes to Kwik Learning, Truity, The Portalist, Insider, and The Nerd Daily. In addition to writing, Jena blogs at and is active on bookstagram as @jenabrownwrites. When she isn’t imagining deadly worlds, she and her husband are being bossed around the Las Vegas desert by their two chihuahuas.

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