Integrating Character Chatbots in English Class

In October, my freshman English class completed reading The Catcher in the Rye and were left with questions. What actually happened in the story? What was the purpose? Did Holden get better? Why does he behave like that? To answer these questions, I decided to enable them to interview an AI-generated version of Holden Caulfield on Character.AI.

Many educators are seeking ways to incorporate artificial intelligence into education in a manner that facilitates learning experiences while still substantiating students’ comprehension and critical thinking. Platforms such as Character.AI offer a broad array of possibilities for teachers to implement engaging assessment techniques that cover a wide range of learning standards. These platforms also expose students to some of the limitations of AI. Here is a three-step process for using Character.AI as a enjoyable assessment tool in an English class.

The assignment aims to achieve five objectives:

  1. Evaluate comprehension of the characters and plot.
  2. Allow students an opportunity to ask questions pertaining to the book that remain unanswered.
  3. Develop AI literacy through students’ evaluation of the chatbot’s effectiveness and usefulness.
  4. Cultivate critical thinking and perspective by generating broad, open-ended, and empathetic interview questions.
  5. Nurture active listening skills through engaging in a safe space conversation with an AI chatbot.

Step One: Preparing the class for the assignment

Begin by conducting an interview with your own “HoldenAI” on the Character.AI platform. It should be noted that these bots can be flawed, exhibiting inaccuracies, misconstruing questions, and mixing up characters and events from their own story. Additionally, there are multiple versions of the same character, as they are user-generated. Prior to assigning this project, interview several bots related to your chosen book, subject, or task to find one that closely resembles the historical or fictional character you have selected. I personally found @Karakter’s Holden bot on Character.AI to be my favorite.

Next, present and generate excitement for the project. Have the class create a list of “burning questions” for the selected character. Demonstrate curiosity by sharing some of the questions you have always wanted to ask. Inform students that they will be interviewing their own version of the character and assessing its effectiveness.

As homework, ask students to register for Character.AI and have them interview their favorite celebrity or historical figure for fun. This step allows students to become familiar with the platform in an engaging manner. Character.AI includes a disclaimer regarding NSFW content and guarantees the blocking of explicit material. However, certain characters, such as villains or movie characters, may use profanity or be aggressive to align with their personality.

Step Two: Interacting with the Platform

After students have gained an understanding of the program, instruct them to craft broad, open-ended questions that demonstrate an understanding of the character’s motivations and personality.

One of my favorite questions for Holden was, “Why did you never call Jane Gallagher?” This question effectively addresses Jane as Holden’s crush, a significant character in his life, whom he never had the courage to call in the book. It delves into a key aspect of Holden’s character—the inability to confront his emotions—while also being broad, open-ended, and a great conversation starter.

This portion of the assignment encourages students to actively listen. They should respond to the bot’s statements rather than swiftly moving on to the next question. Demonstrating recognition of the bot’s responses can be as simple as saying, “Thank you, that was helpful,” or even expressing empathy with a statement like, “I’m sorry to hear that.”

By requiring active listening, the goal is to familiarize students with enough material to evaluate the bot’s effectiveness and enhance their AI literacy. Engaging in this type of conversation will enable many students to understand the strengths and limitations of AI. The reality surrounding AI is more complex than many realize, and it is important for our students to have experiences that allow them to form their own comprehension.

Once students have completed the conversation, instruct them to copy and paste the text into a separate document and submit it electronically. I found the student conversations to be incredibly intriguing. For instance, in one conversation, a student opened up about personal family struggles and found the chatbot to be a helpful confidant. In another instance, a student engaged in a lengthy debate with the bot regarding the rationality of Holden’s actions, breaking down complex emotions into logical and comprehensible elements.

Perhaps the most fascinating conversation involved a student confronting Holden so directly that the bot shrunk in shame and slowly transformed into J.D. Salinger. The bot changed personalities from Holden to Salinger halfway through the conversation.

Step Three: Assessing the Bot’s Effectiveness

In this section of the assignment, students are required to demonstrate their comprehension of the character by comparing and contrasting the chatbot’s comments with the character’s actions, words, and personality as depicted in the book. Students can support their arguments by citing evidence from both the chat and the book. The conclusions will vary from student to student, as the bot engages in a different conversation with each user, providing a fun twist to the assignment.

Here is the essay prompt I used: “Evaluate the effectiveness of the AI chatbot in enhancing your understanding of Holden Caulfield. To what extent did your interview with HoldenAI contribute to your comprehension of his character? In what ways did HoldenAI align with or differ from J.D. Salinger’s portrayal of Holden Caulfield?”

As an example, the Holden chatbot we used inaccurately depicted his brother Allie during the conversation. In the book, Allie is Holden’s younger brother who passed away three years prior due to cancer. The chatbot repeatedly perceived Allie as a girl. At times, the bot believed Allie was a girl that Holden had dated, while at other times, he thought Allie was a superficial sister. In this way, students can observe the flaws in the bots and recognize that they often operate on incomplete information.

Reflection on the assignment

Following the submission of their conversations, we held a class discussion to reflect on the project. Each student shared the highlights or lowlights of their conversation. It was surprising for students to realize that despite using the same bot, each of their conversations with Holden was completely different. This realization helped them understand a more nuanced objective of the project: Questions and active listening matter. The way in which students prompt, listen, respond, and engage significantly impacts the conversation itself.

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