Gather initial thoughts and broad opinions about the book.

1. In the Author’s Note, Averick mentions her desire to write against the grain of typical romance novels, citing the example of authors like Emily Henry and Abby Jimenez. How did this book’s portrayal of a “messy heroine” with clinical anxiety meet or subvert your expectations for the romance genre?

2. How did your feelings about Phoebe as a protagonist evolve throughout the story? What aspects of her personality or journey did you find most relatable or, perhaps, most frustrating as you were reading?

3. The novel blends a humorous tone with serious discussions of mental health, including panic disorder and OCD. How effective did you find this combination? Did the humor make the difficult topics more accessible, or did it sometimes feel at odds with the weight of Phoebe’s experiences?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Phoebe’s quest is kickstarted by a letter from her 18-year-old self, setting an arbitrary deadline that causes her immense stress. Is there a time you felt pressure from a self-imposed goal? How did that pressure shape your actions and feelings?

2. Throughout every crisis in the novel, Phoebe’s friends offer her support and acceptance. Think about the most important platonic relationships in your own life. What role has friendship played in giving you the courage to face personal challenges?

3. Phoebe’s laminated checklist is her attempt to bring order to the chaos of dating and intimacy. What are some strategies that you use to manage stress, anxiety, or overwhelming situations in your own life?

4. The dynamic between Nora and Phoebe highlights how friends can sometimes envy aspects of each other’s lives while still being supportive. How do you and your friends handle moments of comparison or envy?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. Averick comes from a background as a successful social media creator and podcaster, placing Phoebe Berman’s Gonna Lose It among the ranks of other influencer-penned novels, including YouTuber Haley Pham’s Just Friends and podcaster Bobby Finger’s Four Squares. Do you think this influencer-to-author pipeline brings a unique perspective to fiction?

2. The novel explicitly names conditions like emetophobia (fear of vomiting) and Relationship OCD (intrusive doubts fixated on one’s romantic partnership). How does naming these terms allow the novel to participate in broader cultural conversations around mental health?

3. The novel heavily critiques the pressure to achieve life milestones on a socially prescribed timeline. Where else in our culture do you see these kinds of arbitrary deadlines being promoted for social milestones?

Dive into the book’s structure, characters, themes, and symbolism.

1. How does the recurring motif of crossword puzzles serve as a counterpoint to Phoebe’s chaotic, list-driven quest for intimacy? What does this shared activity reveal about the kind of connection she truly craves versus the one she thinks she should be pursuing?

2. Jonathan’s process of coming to terms with his sexuality and Phoebe’s process of accepting her anxiety unfold alongside each other across several key scenes. Which specific moments place their struggles in closest proximity, and what does that proximity reveal about the novel’s treatment of identity and self-acceptance?

3. Consider the scene where Phoebe discovers Jonathan and Finn’s secret relationship. Why do you think the author chose this particular betrayal of trust as the event that pushes Phoebe to abandon her checklist?

4. How does Phoebe’s character contrast with more traditional romance heroines, such as Elizabeth Bennet in Pride and Prejudice or Ellen Olenska from The Age of Innocence? What differences or similarities emerge?

5. The epilogue reveals that Phoebe’s anxiety shifts into a new form, Relationship OCD, after she and Matthew become a couple. What did you think of this ending? How does it subvert or reinforce the typical “happily ever after” romance trope?

Encourage imaginative and creative connections to the book.

1. Phoebe’s final project is a new checklist for managing her anxiety. If you were to help her brainstorm the first three items on that list, what would they be and why?

2. Imagine you are casting a film adaptation of Phoebe Berman’s Gonna Lose It. Who would you choose to play Phoebe, Jonathan, and Matthew? What qualities would you look for in the actors to bring these characters to life?

3. The friends’ group chat plays a fun role in the story, especially in Chapter 27. Write a short group chat exchange between Nora, Meg, Alex, and Jonathan that might have taken place a month after the book’s epilogue. What would they be talking about?