AI Taught Me Shakespeare. It Also Taught Me About Being Human (Part 1 of 3)

Last year I set out on an ambitious challenge: to read every single Shakespeare play.

All 37 of them.

And I did it.

Some plays took time. Henry V stretched over a month. Others, like Cymbeline, took just three days. On average, I finished one every 15 days.

But here’s the twist: I couldn’t have done it without AI.

In 2023, AI chatbots came onto the scene and I had my doubts. A few prompts here and there. Regurgitated, remixed ideas, with hallucinations. But people kept telling me to look again. 

So I set a challenge: If AI is really that good, it should help me understand Shakespeare. Not just skim it. But get it. Could something artificial really help explain the depths of the human soul?

TL;DR: AI didn’t just help me get through Shakespeare. It changed how I think, how I understand language and communication, and, most unexpectedly, how I understand what makes us human.

All’s Well That Ends Well: A Strategy for Reengagement

Learning anything, whether it’s mastering a new language, perfecting a sport, or honing a craft, isn’t just about talent. It’s about endurance. Sticking with something long enough to start seeing patterns. Feeling momentum. Getting curious.

That’s the hard part, isn’t it?

We start with excitement. Then hit a wall. The challenge feels too big, too frustrating. Our attention drifts, and we move on.

That’s what happened every time I tried to read Shakespeare. The archaic language. The convoluted plots. The obscure references. It wore me down. I didn’t have time for it. I wanted to watch White Lotus instead.

To get started, I opened ChatGPT on my phone:

• What’s actually happening in this play?

• What does this phrase mean?

• How did audiences in 1600 interpret this moment?

Little by little, I got curious. I got confident.

Suddenly I wasn’t just reading, I was in conversation with AI. With someone who didn’t get tired of my long-winded thoughts as I tried to work through Shakespeare’s most convoluted ideas.

Take All’s Well That Ends Well. The ‘bed trick.’ A woman deceives her husband into sleeping with another woman, but it’s actually her under the sheets. That’s the plot. And she’s the hero of the play?!

I argued with ChatGPT for two hours. How could this be OK? How could this be heroic?

But the bot kept nudging me to view the play through a 17th century lens. Eventually, it clicked: Her deception forced him to confront his arrogance and rescue him! All the women in the audience must have related to her and rejoiced when she got the ending she wanted.

AI gave me the patience to stay with the discomfort without judgment. I don’t think a professor would’ve put up with me that long. And most of my friends would have changed the subject. I talked it out, I figured it out.

Coming up next:

In Part 2, I’ll unpack how Shakespeare’s language works like a hidden code: layered, emotional, and full of subtext. And how AI helped me slow down and actually hear what’s meant, not just what’s said.