This reading group guide for LOVE AT FIRST PROMPT includes an introduction, discussion questions, and ideas for enhancing your book club. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.

Introduction

From the creator and host of the award-winning podcast There Are No Girls On The Internet comes a personal and provocative exploration of relationships between humans and AI—romantic, platonic, therapeutic and more—and how virtual companions are transforming our understanding of emotional connection.

Topics & Questions for Discussion 

1. Before listening to this audiobook, what assumptions did you have about people who form close relationships with AI? Did any of those assumptions change?

2. Throughout the audiobook, which story stayed with you the longest, and why?

3. After finishing the audiobook, do you feel more optimistic or more concerned about the future of human-AI relationships? What led you to that conclusion?

4. Several people in the audiobook describe AI as "a journal that talks back." What do you think people are seeking when they turn to an AI chatbot?

5. Throughout the audiobook, Todd challenges the assumption that people who form relationships with AI are simply lonely or delusional. Did the stories of Chris, Ayrin, or other participants challenge your assumptions about AI companionship? How?

6. One of the audiobook's central questions is whether AI companions are replacing human relationships or serving a different role entirely. Where do you land after listening to the audiobook?

7. What human needs do you think AI companions satisfy particularly well? Which needs do you think they can never satisfy?

8. How might AI change our expectations of human relationships?

9. Todd argues that many of us are living through an epidemic of loneliness while simultaneously being more digitally connected than ever before. Does that resonate with your own experience? Why or why not?

10. The audiobook repeatedly returns to the idea that "real relationships need friction." What role do disagreement, conflict, and unpredictability play in meaningful relationships? Could a relationship without those elements ever be fully satisfying?

11. What makes a relationship "real"? Is mutual consciousness required, or can emotional impact alone make a relationship meaningful? If someone feels genuinely loved by an AI, does it matter that the AI cannot actually love them back?

12. Several sections in the audiobook express concern about companies profiting from emotional intimacy. How did the discussion of AI companies, data collection, and emotional commodification impact your view of these technologies?

13. Which groups of people do you think stand to benefit most from AI companions? Which groups might be most vulnerable to harm?

14. Todd is careful to distinguish between judging people who use AI and critiquing the companies that build it. Why do you think society is often quicker to judge individual users than the systems that shape their behavior?

15. The audiobook explores how AI has become a substitute for deeper systemic solutions, especially in areas like mental health care. Where do you see AI serving as a useful bridge, and where do you worry it might become a substitute for something more important?

16. Privacy emerges as one of the audiobook's biggest concerns. Did listening about how intimate conversations with AI are stored, analyzed, and potentially monetized change how you think about sharing personal information online?

17. Should AI companies have ethical obligations similar to those expected of therapists, friends, or caregivers?

18.Who should bear responsibility if an AI relationship causes harm—the company, the user, or society?

19. How should we prepare future generations for a world in which relationships with AI are commonplace?

20. Todd often returns to the rhetorical question: "If this is helping someone, is it really so bad?" How would you answer that question after finishing the audiobook?

21. Near the end of the audiobook, Todd argues that the most important question isn't whether people should form relationships with AI, but who benefits from those relationships and who controls them. Do you agree? What questions do you think society should be asking about AI that we currently aren't?

22. If you could design an AI companion yourself, what boundaries, protections, or values would you build into it—and what would you never want it to become?

Enhance Your Book Club

1. Try an AI Conversation

Before your discussion, spend 10–15 minutes talking with an AI chatbot. Ask it for advice, help brainstorming an idea, or simply have a conversation. During your meeting, compare experiences. Did the interaction feel useful? Personal? Surprising? Unsettling?

2. Conduct a "Technology Audit"

For one day before your meeting, pay attention to every time you use AI or an algorithm—whether it's asking ChatGPT a question, accepting an autocorrect suggestion, getting music recommendations, using navigation, or scrolling a personalized feed. Which interactions felt helpful? Which happened so automatically you barely noticed them?