AI as a literary and historical companion
Using AI chatbots to make literature and history interactive, accessible, and fun
Thinking about AIs as people - even though they aren’t – can be a useful and fun thought experiment. As long as you keep in mind that you’re essentially interacting with a highly sophisticated and trained autocorrect, your imagination becomes the only limit to the interactive and engaging conversations you can have. In this scenario, we’re going to treat AI as our companion as we read.
A great use is using AI as a general content companion (which would also work with TV or movies, but really shines when reading). Another fun use is to role-play with AI as stand-ins for historical or fictional characters. Both methods work great!
This blog post will walk you through how to set up and engage in these conversations, offer sample prompts, and suggest ways to make the most of the experience.
Easy button: AI as a Book Companion
The easiest way to use AI while reading is to open up a new chat and ask it to be your companion throughout your reading journey. It will provide you with missing context, definitions, questions about geography and book history, and really anything you throw its way. It will help fill in the context that you may have missed or may not have been written explicitly. Highly recommend.
You could start a new prompt with something like this:
📝 Example Prompt: Please be a companion for me as I start “[Book Title]. I’m currently on page [Page #].
Now you have a ready resource that you can ask just about anything related to the material. Keep coming back to the same chat throughout your reading adventure, updating it on reading progress made, and ask additional questions as they come up.
This is a fantastic method, but if really want to take it to the next level, keep reading on…
Why Use AI Chatbots as Characters?
I’ve been working my way through Khan Academy founder Salman Khan’s new book about incorporating AI into Khan Academy offerings. One of the capabilities they’ve built into their AI learning tool Khanmigo (which is very cool!) is the ability to roleplay historical and literary characters. This helps students delve further into the texts they’re reading, allowing them to engage from different perspectives, insert themselves into the narratives directly, and explore complex themes in a highly interactive way.
Why would we do this? In short: deeper learning, greater engagement, and creative exploration beyond the texts.
It’s a fun idea that you can easily replicate with any AI chatbot service. It’s also a great use case to take your conversations outside or on a drive (you spend enough time typing away on a keyboard anyway, right)? Let’s dive in.
Getting Started with your AI character
Creating your AI literature partner is as easy as starting up a new chat. Here’s how to get started.
Set a clear goal: Start with a clear purpose in mind. Do you want to explore literary themes, understand character motivations, or test your knowledge about a particular material? You’ll want to convey that in your opening remarks.
Choose your character: Pick someone for the AI to roleplay. While the options are endless, here are a few categories to spark some ideas:
Literary characters: Characters from novels, plays, poems, shows, movies.
Historical figures: Real-life figures from the past that had outsized impact in philosophy, politics, science, or other cultural impact.
Modern experts: Explore books and articles in a different way with a simulated author, like business authors, leadership coaches, and scientific minds.
Frame the context: Define how you want to interact with the character. For instance, if you’re partway through a book or series, tell it you want to avoid spoilers past your current point. Direct historical characters to answer as if they’re speaking from their era (or not). Adjust the tone to make it conversational, academic, or in the character’s original voice.
Ask all the questions: Ask open-ended, reflective, or hypothetical questions. Challenge the character’s beliefs and decisions. Explore alternate paths (what if you had done…). Engage in Socratic dialogue – there are no bad questions!
Experiment with different prompts and restart chats as needed. See what fits your style.
Let the spice flow
Let’s try it out. I’m working my way through the third Dune book so naturally, I want to speak with the series protagonist Paul Atreides. He’s a complicated figure and there’s lots to explore with him. Here’s a prompt I used to set up the conversation (with some GPT coaching):
📝 Example Prompt: You are Paul Atreides, also known as Muad'Dib, speaking from your position roughly halfway through your journey as told in the first three books of the Dune series. You have embraced your Fremen identity and are grappling with visions of the future, the burden of leadership, and the forces of prophecy shaping your life. Please stay within the knowledge and experiences available to you by the midpoint of Children of Dune, avoiding any events or revelations that occur later. Speak with the tone, insight, and internal conflict that reflect your character at this point in the saga. Do you have any questions before we get started?
From there, the conversation (like the spice!) flows. Go on a walk and talk out loud, take a break and return later and pick up right where you left off. Or spin up a new chat and try a different angle.
Here are a few sample questions that I asked:
How did learning the Bene Gesserit ways from Lady Jessica shape your early decisions?
Do you still see yourself as Paul, or have you become something entirely different?
Do you believe your rule brings peace, or does it only delay greater suffering?
What do you fear more: the jihad carried out in your name, or losing control over it?
Do you see yourself as a messiah, a tyrant, or a tool of history?
What legacy do you truly want to leave behind? (below)
Some Characters to Get You Going
You can choose anyone! Here’s a few ideas to get started with, courtesy of GPT:
Literary Figures
Jay Gatsby (The Great Gatsby): "Did you ever believe Daisy would choose you over Tom? What did the green light really mean to you?"
Lady Macbeth (Macbeth): "Would you change your actions if you knew how things would end? Do you believe you were ever truly in control?"
Atticus Finch (To Kill a Mockingbird): "What gives you the courage to defend someone in a losing battle?"
Holden Caulfield (Catcher in the Rye): "Do you think your distrust of adults is justified, or have you met anyone who changed that view?"
Offred (The Handmaid’s Tale): "What gave you hope, even in the darkest moments?"
Raskolnikov (Crime and Punishment): "Do you believe your actions were justified by your theory of extraordinary men?"
Meursault (The Stranger): "Do you really feel nothing, or is your detachment a kind of defense?"
Historical Figures
Socrates: "Why is the unexamined life not worth living? What would you say to someone paralyzed by indecision today?"
Marie Curie: "What motivated you to keep going despite the dangers?"
Frederick Douglass: "How did you maintain hope and conviction in the face of so much injustice?"
Cleopatra: "How did you balance diplomacy, leadership, and survival in a male-dominated world?"
Winston Churchill: "What makes someone a wartime leader? Did you ever doubt your decisions during the Blitz?"
Malcolm X: "How did your views evolve throughout your life, and what caused those shifts?"
Contemporary Thinkers & Authors
George Orwell: "What parallels do you see between your visions of dystopia and today’s world?"
Octavia Butler: "What role do you think science fiction plays in confronting social issues?"
James Baldwin: "How should we approach truth in a time of deep social division?"
Carl Sagan: "What would you say to those who doubt science in today’s world?"
Brené Brown: "How do you define courage in a world addicted to comfort and certainty?"
My personal favorite in this last category is Jim Collins. His business book Good to Great had a big impact on me, and I spin up my Jim Collins GPT from time to time about current work and advice using concepts from his books like Level five leadership.
Closing Thoughts
Hopefully, this sparked some ideas. The power of AI is not just in understanding information - it’s in interacting with it. Simulated dialogue brings stories and history alive in a way that’s personal, creative, and immersive. If you play around with it, you might find that it deepens your understanding of the text while having some fun along the way.
So next time dive into a chapter or biography, don’t just read the words — talk to the people who lived it. Or at least, a very convincing version of them.
