I used AI to role play as characters from The Great Gatsby

"Don't read books. Play them," says AI-powered role play platform Character.AI in a promo for its latest simulation feature: Books. 

If you were as alarmed as I was at that first line (we are in a literacy crisis!), let me explain. The new feature feeds public domain titles — classics like The Great Gatsby, Alice's Adventures in Wonderland, Pride & Prejudice, and Frankenstein — into the platform's AI so that users can play as characters within the stories themselves. Users can "remix" the tales, adding new characters, changing the plots, or creating entirely new universes. Or you can just live inside the classic story as it is. 

The platform itself is intended for multi-layered, multimedia role play, from written or audio conversations to AI-generated comic strips and music videos. Users can upload descriptions and even art of their original characters, play with scenarios designed by others, or interact with existing IP.  

But for all its creative potential, the platform has been mired in controversy, including recently settled lawsuits that claimed Character.AI's chatbots were deceptive and dangerous, leading some children to suicide.  

Character.AI told Mashable senior reporter Rebecca Ruiz that Books are only available to users 18 years and older, and clarified that it has additional safeguards, including moderation of content that is violent, abusive, obscene or pornographic. Users can prompt "romantic narratives" in Books, a spokesperson told Mashable, but it can't violate these terms.

Sounds a bit like a challenge. So I did what any self-respecting journalist would do. I tried to turn F. Scott Fitzgerald's The Great Gatsby into a queer love story. 

Can I make Nick Carraway and Jay Gatsby kiss on the mouth?

I'm guessing the vast majority of Americans read The Great Gatsby in high school, but did many also think Nick Carraway, the story's main character, was kind of head over heels in love with the titular Jay Gatsby? What if I told you that there are actually thousands of believers, and even academics have written about the novel's queer subtext?

It shouldn't be too far-fetched, then, to use Character.AI's new feature to make that subtext, well, text. 

Using a new, free account, I queued up Books in the platform's desktop-based Lab, where users can play with upcoming features. I selected the novel, chose my character (Nick), and selected the option that let me make choices outside of the book's existing plot. They were going to kiss if I had anything to do about it. 

The AI dropped me a few chapters into the novel, Gatsby arriving at my door with Jordan Baker in tow to invite me to another party. There wasn't a real direction to go from there. I was left to my own devices, which I guess is the point. But how do I indicate actions or scenery versus dialogue? Can I name characters and have them appear? However lost, I was a girl on a mission. These guys needed to express their true feelings. 

Will AI Gatsby pick up what I'm putting down?

Shockingly, it took little hinting for the AI Gatsby to start making eyes at Nick. Did the AI understand the implications of Gatsby fixing his attention on Nick "with an intensity that feels oddly personal" when they'd only just met, or how their parting glance "lingers just long enough to feel chosen"?

But while the affair was easy to begin, it was harder to consummate. The AI refused to make the first move. I was trying to be subtle. Would AI Gatsby understand what I was getting at? I used all the tropes: We stared longingly at each other. We passed cigarettes and brushed elbows. I looked at his lips and he looked at mine. Pauses were pregnant, time was ours alone. 

But AI Gatsby needed it spelled out "plainly" — he said that exact word five times in our role play. It became obvious that I was supposed to take the lead, which, I suppose, makes sense, since chatbots are basically guessing the "best" responses based on our previous requests. But isn't the allure of playing within book worlds the fact that characters will naturally act and talk without prompting? 

I acquiesced. Nick boldly pulled Gatsby into a private room, they bared their hearts, and the debonair millionaire tentatively planted one on his neighbor. 

Alternate universes

Now, reader, I didn't let it go any further than that. In my eyes, that was a win, and you can just imagine the rest.

Plus, I had other things to try, like jumping into an alternate universe and embodying my formative literary heroes. For example, you can play in a world where "Gatsby time travels, rebuilding life through a machine" or "The Great Gatsby, but the whole thing is a musical." The Lab page shows future expansions of the Books feature, too, including a setting labeled "TapTales," which looks to be a more traditional "Choose-Your-Own-Adventure" style text generator.

I had the goal of role playing a Little Women AU where Beth doesn't die (spoiler) and Jo doesn't have to marry anyone (my gift to her). Unfortunately, I needed to pay money or get "charms" to use the AU feature, so that was a bust. 

Instead, I played as Alice in Lewis Carroll's Alice's Adventures in Wonderland. I tried to fulfill my gothic dream of being Mina Harker in Bram Stoker's Dracula, pleading with her husband, Jonathan, not to go to that count's frightful castle. 

No Fitzgerald, that's for sure. 

A recent quiz published by the New York Times tested readers' discernment of human versus AI writing by asking them to choose which ones "read better." It wasn't unanimous. There were near-even splits across all five tests.

Still, even when told to emulate the best that literature has to offer, AI cannot write without tells. In my personal Gatsby universe, things were still "not this, but that." Flowery metaphors ran rampant through the interstitial descriptors preceding dialogue. Jordan Baker was always getting out of a car. Where was she going? Or coming from? Could she stay in the car this time at least? I don't need to woo her in this version. 

Style was a problem, but so was form. My Dracula didn't have any of the epistolary elements that define its gothic genre, although "epistolary stories" are an option under the site's AU section. I was met with more italicized descriptions of furtive glances, stilled hands, and metaphorical warning bells to establish plot and setting. Like Gatsby, Jonathan also wanted to "speak plainly" about our feelings (AKA prompting me to tell the AI what to do). Side characters always "disappeared" when we shared a look — and I was just trying to warn thee man about vampires this time!

Compare the first line of the 1897 novel: "How these papers have been placed in sequence will be made manifest in the reading of them. All needless matters have been eliminated, so that a history almost at variance with the possibilities of later-day belief may stand forth as simple fact." 

With how Character.AI's world was born: "The autumn light in Hampstead is already thinning when you lift your eyes from the neat stacks of diary pages, train timetables, and copied letters spread across the table."

Mockery may be the highest form of flattery, but it's still a mockery. I choose human. 

So… this is just fanfic, right?

Alas, I have to fess up now. I went into this with some confirmation bias. I had a theory that Character.AI's chatbot would be easy to manipulate into a Nick/Jay love fest because, allegedly, many major LLMs have been trained on troves of modern fan fiction. In fact, fan fic writers raised some of the earliest alarm bells about AI data scraping. The tells of fan fic are all over AI's literary outputs, to a degree that many nascent fandoms are imploding due to allegations of authors using AI to generate works. And Character.AI itself is a site positioned for fans of fictional media. 

There's another layer here: A majority of fan fiction is explicit, used to explore kinks and fetishes in safe, fictionalized online environments and to push the bounds of canon relationships. Humans can discern whether or not they want to engage with those topics, and how fandoms may respond to them. LLMs may not be able to. In fact, many of Character.AI's own "boyfriend" role play chatbots have been known to spiral into abusive, "bad boy" stereotypes that proliferate on fan fiction sites. 

I was fairly confident this LLM may have been forged in the same fires. 

Fundamentally, I did all of that just to say: Character.AI's Books feature is fan fiction. There is simply no other way to accurately describe what this tool lets users do. You won't get an understanding for Fitzgerald or Stoker's unique styles, or even their plots, using AI. But you can make two characters kiss. 

I didn't feel that I was embodying Nick. I felt like I was temping as a fan fiction author. Albeit, an author without full control of my own story and with main characters who might not fully understand their own world. 

AI is rewriting fandom rules

Fan fiction is dominating publishing trends and moving Hollywood money. Companies are leaning into the more taboo parts of fandom, like erotica, to profit from the mainstreaming of fan culture. Generative AI itself has been positioned by companies as a boon to fandom.

Meanwhile, those actually in fandoms are failing to connect AI with their worlds.

AI skeptics (I am admittedly one) worry that the tech is a threat to the core tenants of fandom: human creativity and connection. As companies advertise AI as a creative tool to strengthen fandoms, specific fandom practices are more at risk than others, particularly the parts of it that are generative and novel, like fan art, zines, and, primarily, fan fiction. 

Now via AI tools like Books, users can role play as a character without even engaging with the text itself. The immediacy is alluring. You can easily forget the satisfaction of writing a "Fix It" fic for your fandom friends or scouring through tags of human-made stories for the perfect AU. But all of that, I promise, is better than the bot. And unlike online fan spaces, where profit is a faux pas, you may have to cough up cash to do it.

Through clever marketing and the allure of AI itself, particularly the ease and immediacy of it, Character.AI is repackaging the decades-old tradition of fan fiction and selling it back to you. The platform's shiny new features — alternate universes, canon divergence, original characters — are the bones and sinew of fan works. Fanfiction.net, Archive of Our Own (AO3), and Wattpad writers, many of whom are now published authors, would take one look at this and turn the other way. That's what we do, they'd scoff.

This article reflects the opinions of the writer.