Because of ChatGPT, I Find It Easier to Relate to Shakespeare’s Characters

Like most people, you might find it hard to understand Shakespeare, let alone relate to his characters. Take these lines spoken by King Richard II in Act 3, Scene 2 of the play Richard The Second, for example:

Huh?

Without context, the language is not only difficult to grasp, but it’s hard to feel for King Richard II. He’s a terrible king, and yet I’m supposed to empathize with him when he admits he needs friends? Am I supposed to feel pity? Ugh…

Project Shakespeare

Over the past eight months, I’ve read 16 Shakespeare plays. It's a project I devised for myself. The reason I can power through them now, as opposed to five years ago, is because of AI technology — specifically, OpenAI's ChatGPT.

It’s been a lifelong dream to read through Shakespeare’s entire canon. With each play I study (about two weeks per play), I’m struck by how deeply Shakespeare explores human nature — especially around power and leadership.

And to be honest, most of my friends are tired of talking about Shakespeare with me. That’s why I’ve turned to ChatGPT, which has become a constant companion, helping me process the plays and offering insights — even at 1 a.m. when everyone else is asleep.

I want to share with you three ways (with video examples on Instagram Reels) I've prompted ChatGPT to better relate to Shakespeare’s characters. These case examples show how AI technology can help us connect more deeply with others — whether they’re fictional or real, friend or foe, someone we know personally, or even someone maybe running for office....

Comprehension Checking: Prince Hal in King Henry IV, Part 1

If you read my first article on how ChatGPT helps me decode Shakespeare, the initial prompts I used were fairly basic, like:

• “Can you give me a high-level overview of this scene?”
• “What does this sentence/word mean?”
• “Who is this character?”

Six months and 16 Shakespeare plays later, I’ve learned a lot about studying Shakespeare. I’m less reliant on ChatGPT now. When I do get confused, instead of asking ChatGPT a question and waiting for an answer, I ask ChatGPT to listen to me. This shift has transformed how I interact with AI.

For example, when I began reading King Henry IV, Part 1, I was introduced to Prince Hal. Since Shakespeare devotes three plays to this character, I knew I needed to invest in understanding him. But instead of asking ChatGPT, “Who is Prince Hal?” I studied the first scene he appears in. Then, I told ChatGPT what I thought was happening and asked if I was on the right track.

Here’s what I said, more or less, in a stream-of-consciousness, rambling, run-on sentence, before ChatGPT could interrupt me (which it frequently does):

“I just finished Act 1, Scene 2 of King Henry IV. I was introduced to Prince Hal. If I’m understanding this right, he’s talking with a guy named Falstaff, and he’s being pretty rude, but I guess they’re friends because friends can say stuff like that to each other. They’re planning to rob some people at Gad’s Hill, even though Hal is a prince and doesn’t need the money. Then, at the end, he says that one day he’ll reveal that all these shenanigans were just so people see that he’s an authentic leader because he didn’t suck up to his dad, the king. Does that make him more likable to commoners? Did I get that right?”

ChatGPT’s response? Sometimes it tells me, “You’ve got the gist of it!” Other times, “Your observations are partially correct.” Occasionally, “That’s not quite what’s happening.” But this time, it said, “You’re on point.”

I’ve always believed in learning by doing. Active learning is key. Instead of asking ChatGPT to tell me what’s what, I ask it to listen to me and confirm my understanding. Boom!

As a teacher and lifelong learner, this makes sense to me. When starting to learn something new, we don’t have the words. But after a few experiences, we start to piece ideas together and test them out. The best part? AI technology is endlessly patient. I can ramble, feed it convoluted, half-formed thoughts as they emerge in the moment, and it listens. When I do this with friends, they usually groan.

Perspective Taking: Isabella and Angelo in Measure for Measure

Measure for Measure is one of Shakespeare’s problem plays, so-called because its central conflict is so strange.

Here’s the plot in a nutshell: the antagonist, Angelo, revives an old law against premarital sex, punishable by death. Isabella, the sister of the man convicted under this law, pleads for mercy. Angelo responds by demanding that she sleep with him in exchange for her brother’s life. The twist? She’s just joined a nunnery.

But that’s not even the weirdest part. To save her virginity and free her brother, Isabella agrees to trick Angelo. She pretends to consent to his demands, but when Angelo enters the room expecting to sleep with her, it’s actually his ex-fiancée, Mariana, waiting for him. And somehow, this is all okay?

The only way I could make sense of this bizarre plot was by asking ChatGPT questions like:

• “Explain this scene from Angelo’s perspective.”
• “Explain this scene from Isabella’s perspective.”
• “Imagine the play was told from Mariana’s point of view. What’s the story from her perspective?”

ChatGPT can walk me through the plot from any character’s point of view—even the most minor ones. It’s hard to believe even the most erudite Shakespearean scholar could instantly explain a play from anyone’s perspective as quickly as ChatGPT can. It makes me wonder if we could use this technology to foster empathy for real people who are often misunderstood in complex situations. That leads to me to the next prompt I discovered through my Shakespeare Project.

Relating to Difficult Characters: King Richard II in King Richard II

It’s hard to relate to people who have very different lived experiences. Try relating to King Richard II. He’s a spoiled royal who believes in the divine right of kings—so don’t even think about questioning his legitimacy to rule. Yet, King Richard II wants us to sympathize with him when he confesses he’s just like everyone else? That he feels want, tastes grief, and needs friends? Spare me.

Here’s how ChatGPT helped me relate to someone I initially couldn’t stand. I asked it:

“Please ask me 10 questions that will help me relate to King Richard II. Ask one question at a time and listen to my responses before asking the next one. After hearing all my answers, draw connections between my life and the character’s experiences to help me empathize with him.”

And it worked.

Yes, I poured my heart into every question ChatGPT asked. The more I shared, the better it could help me relate to Richard. It worked so well that when I watched the recent BBC adaptation of King Richard II with Ben Whishaw, I actually felt for Richard during his beachside confession. Despite his privilege, when he admits he needs friends, I pitied him—and I cried.

Damn. ChatGPT helped me feel for someone I once thought was un-relatable to me.

Let me know in the comments what you think about using ChatGPT to navigate tough social situations or how you’ve used AI to gain insights into the human relationships.