If It Makes You Happy

Gather initial thoughts and broad opinions about the book.

1. Discuss your overall impressions of If It Makes You Happy. What were your favorite and least favorite aspects of the novel, and why?

2. How did your experience reading If It Makes You Happy compare to your experience reading Olivia’s other books? What parallels do you notice between this novel and Olivia’s The Fake Santa Apology Tour (2021) or All Downhill with You (2022)?

3. How does Olivia’s handling of the romantic comedy genre compare with other takes on the genre? What plot and theme overlaps do you notice with novels like Emily Henry’s Funny Story (2024), Ashley Poston’s The Seven Year Slip (2023), or Sally Thorne’s The Hating Game (2016)?

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

1. How did you respond to the scene where Michelle sets up Sara with Cliff? Have you ever set up a sibling or friend with one of your romantic interests? What were your reasons for doing so, and how did they compare to Michelle’s? What was the result of the setup?

2. Michelle and Cliff’s relationship gradually develops from friendship to love. Compare and contrast their friends-to-lovers arc to your own romantic history. Have you ever fallen in love with your best friend? If so, what were the results?

3. Michelle’s relocation to Copper Run unexpectedly changes her perspective on life. How have your own geographical relocations upended your definitions of home, belonging, and happiness?

4. How does Copper Run compare to a small town you’ve lived in or visited? Which aspects of small town life do you like or dislike, and why?

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

1. If It Makes You Happy is set in 1997. How does this setting affect the novel’s plot? Consider how the absence of technology impedes or facilitates the characters’ relationships. Why does Olivia not use this historical setting to create a deeper sociopolitical commentary?

2. Michelle ultimately gives up her metropolitan dreams to settle down in rural New England with her new boyfriend. How does the trajectory of Michelle’s story fit into or subvert the tenets of third-wave feminism? Is Olivia’s novel socially aware? How might Michelle’s Conflict Between Ambition and Rootedness relate to 1990s feminist ideals?

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

1. The novel is written from Michelle’s and Cliff’s alternating first-person points of view. What are the narrative and thematic effects of this structure? How would the novel be different if written from Michelle’s point of view alone?

2. Compare and contrast Allen and Cliff, and Tracy and Michelle. How is Michelle and Cliff’s relationship different from their relationships with their exes?

3. How do the novel’s references to 1990s culture, media, and entertainment relate to the novel’s themes? How does the novel uphold or subvert the romance genre tropes these other works contain?

4. What other symbols did you find in the novel besides those mentioned in this guide? What is their significance? For example, what do Michelle’s pendant, Burke’s Bakery, and Michelle’s birthday cards represent and how do they contribute to the novel’s themes, mood, or conflicts?

5. How do the novel’s settings, like Copper Run, the inn, and the bakery, impact Michelle and Cliff differently over time?

Encourage imaginative and creative connections to the book.

1. Imagine that, like Michelle, you fall in love with someone on the other side of the country. Would you give up your dreams and relocate to be with your new lover? Would you attempt a long-distance relationship? What would you do similarly or differently from Michelle? How does your personal experience inform your thinking?

2. Imagine that you are adapting If It Makes You Happy into a feature film. Who would you cast in the leading roles? Which songs would you put on the soundtrack? Which plot points would you add, omit, or alter to make the adaptation your own? Consider how 1990s romantic comedies might inform your adaptation, too.