P.S. If you’ve already read the book, feel free to add any other discussion questions of your own in the comments!
Olivia and her best friend Adrienne are best friends and worst enemies simultaneously. Have you ever been in a toxic friendship?
1. Olivia is different from a lot of YA protagonists in that she is a cruel and manipulative mean girl. She talks about the thrill and adrenaline she gets from drama and power, but she also hates herself for her being a bully. Did you find this an interesting change from the usual hero story? Or did you find Olivia hard to stomach?
2. Olivia’s road to redemption is a rocky one. Even as she begins to realize that she has to change for the better, the temptation to do bad things keeps pulling her back into her old life. Did you think her character arc from mean girl to mean girl-in-recovery was a sympathetic one? Did your feelings toward her change over the course of the story?
3. This is a book about bad people who occasionally do good things, and good people who occasionally do bad things. Did you have a favorite secondary character? Was there a character you loved to hate?
4. Adrienne has a near hypnotic control over Olivia and everyone else around her, despite being ruthless toward all of them. Did you find Adrienne’s ability to manipulate others believable? And did that affect how you felt about Olivia, Claire, and the other girls stuck in her gravitational pull?
5. What did you think of the romance – both real and fake – between Whit and Olivia? Did you find it compelling? Did your feelings about their “relationship” change as Adrienne made life more difficult for them?
6. Olivia talks a lot about her town, Buckley, and how she fears that she’s stuck in it forever. How much did you think the town of Buckley shaped its inhabitants? Was Buckley, at least in part, the reason why Olivia and Adrienne were the way they were? Why or why not?
7. In the same vein, how much did you think that Ryan’s death shaped Olivia? She blamed her bad behavior on losing him, but the flashbacks between chapters showed us that Olivia was capable of doing bad things before he died. Did you think that, in death, Ryan played a bigger part in Olivia’s choice to be bad or to put her past behind her?
8. How to Break a Boy is dark, raw, and visceral. Based on its title and cover, were you surprised by the cruelty and complexity of the writing?