Chapter 33 Summary, Analysis, and Key Takeaways

⚠️ Spoiler Warning: This guide contains detailed spoilers for the entire novel. Proceed only if you've finished reading or are comfortable knowing the plot.

Summary

Nine days before her disappearance, Willow writes another unsent letter to Dominic, admitting that her letters have become more of a diary than correspondence. She explains that writing to him—even without sending—helps her hold on to her sanity and feel connected to him. She plans to keep writing and eventually send them all at once.

Willow describes her relentless search for Jacob across Clifford Island. When she is not at church or youth group, she hikes through forests, walks roads, and visits the island cemetery, reading every headstone. She notes the mix of ancient and simple markers, including graves from the Clifford Sickness. She does not find Jacob's name, but she feels compelled to keep looking. She repeatedly checks downtown stores and buildings, but there is no trace of him.

The one constant she encounters is the boombox man, who plays “Livin’ on the Edge” every time she sees him. She finally approaches him and asks why he plays it so often. He shrugs and says it makes him feel good. Willow reflects that the song feels like her theme song, as if she will live every day on Clifford on repeat forever.

At night, she walks the beaches in the cold, humming the song, hoping for a sign. She admits there is no real reason Jacob would be on the beach, but the waves bring her a measure of peace and hope. She has even tried saying the words “I just want my boy back,” but nothing happens. She insists the earlier supernatural event was not a dream.

Her near breaking point comes when she sees a group of children playing baseball. One boy’s mitt looks like Jacob’s, so she sprints over and grabs it to check for the initials “J.S.” The boy is startled, and his sister, playing with a pink Skip It, looks confused. The mitt is not Jacob’s. Willow realizes she probably looks deranged and jokes about being tied to a boat and set on fire like a Viking funeral.

Later, she unloads on Lily from the youth group after the other members leave. Lily listens but mostly says that the island’s rejection of technology is simply “the way things are around here.” She compares the island to a cult or commune, where adults prefer things a certain way. Lily is not a fan and cannot wait to leave for college.

Willow shares more about her past with Lily. She tells her about Harper, her husband, who is a sports reporter, and about how they met in college, their marriage, Jacob’s accident, and how she stumbled across a job opening on Clifford. Lily asks why anyone would come to the island, and Willow laughs.

Willow then tells Lily the story of her last year teaching. A student asked for a recommendation letter for a scholarship. Willow wrote a glowing letter, but when the student read it, she looked mortified. Willow had mixed her up with another student—she wrote the letter about Avery, but the student was Paige. Willow realized she had been teaching the student for almost two semesters and still got it wrong. She felt like a monster and decided to leave teaching. She tells Lily that she plans to look up Paige someday and apologize.

Willow does not tell Lily about the words on Jacob’s floor or about seeing Jacob the other night. She asks Lily to keep their conversation between them, and Lily swears she will. Willow reflects that Lily is a good kid, bright and personable, and she hopes Lily follows her hoop dreams.

Finally, Willow learns that Lily’s father is the city clerk on Clifford. Willow asks Lily if she has heard anything about a woman named Gloria who died on the island, but Lily says she has not. Willow believes Lily is sincere. She reasons that her father would have records of deaths on the island, and she resolves to find out.

Key Events

Willow writes an unsent letter to Dominic, nine days before her disappearance, as a coping mechanism.
She searches the island extensively: forests, cemetery, downtown stores, and beaches at night.
She confronts the boombox man about his repeated song; he says it makes him feel good.
She mistakes a boy’s baseball mitt for Jacob’s and grabs it, causing a scene.
She confides in Lily, who explains the island’s technology ban as a cult-like norm and plans to leave for college.
Willow shares her backstory, including the recommendation letter mistake that ended her teaching career.
She asks Lily about Gloria, but Lily knows nothing.
Willow learns Lily’s father is the city clerk and decides to investigate his records.

Character Development

Willow’s desperation deepens in this chapter. Her search for Jacob becomes all-consuming, and she admits to feeling alone and on the verge of breaking. Her decision to write unsent letters shows her need for connection and her struggle to maintain sanity. The incident with the baseball mitt reveals her fragile emotional state—she acts impulsively and then fears being labeled a “crazy lady.”

Her conversation with Lily allows her to open up about her past, but she still withholds her deepest secrets. She shares the story of the recommendation letter, which exposes her guilt and her desire for redemption. She wants to help one kid—perhaps Lily—to make up for her past failure. This shows her longing for purpose and her belief that helping someone might make things right.

Lily emerges as a trustworthy and empathetic listener. She is perceptive, asks probing questions, and offers a candid view of the island as a cult-like place. Her ambition to leave for college contrasts with Willow’s entrapment. Willow’s decision to investigate Gloria’s death marks a shift from passive searching to active investigation, suggesting she is willing to uncover the island’s secrets.

Themes, Symbols, or Motifs

The recurring song “Livin’ on the Edge” symbolizes Willow’s feeling of being stuck on repeat, living each day on Clifford without progress. The boombox man’s simple answer—that it makes him feel good—highlights the island’s acceptance of repetition and stagnation.
The letters to Dominic serve as a coping mechanism and a motif of connection. They represent Willow’s need to maintain a link to her old life and her struggle to process her isolation.
The cemetery and the city clerk’s records symbolize the island’s history and the secrets buried within it. Willow’s reading of headstones and her plan to check records show her determination to uncover the truth about Gloria and possibly about Jacob.
The cult-like community is a theme explored through Lily’s comparison. The island’s rejection of technology and its insistence on “the way things are” suggest a closed, controlling society.
Guilt and redemption are central to Willow’s backstory. The recommendation letter mistake represents her failure as a teacher, and her desire to help Lily or find Paige reflects her need for atonement.
Secrets are a motif: Willow hides the words on Jacob’s floor and her vision of him, while the island itself seems to hide the truth about Gloria and other deaths.

Why This Chapter Matters

This chapter deepens Willow’s character and sets up a new mystery. It reveals her past as a teacher and the guilt that drove her to Clifford, making her more sympathetic and complex. The introduction of Gloria and the city clerk’s records gives Willow a concrete lead, shifting the narrative from a passive search to an active investigation. It also reinforces the island’s oppressive atmosphere and Willow’s isolation, while showing her growing trust in Lily—a relationship that may prove important later. The chapter’s focus on secrets and the need to uncover them foreshadows the revelations to come.

Study Questions and Answers

1. Why does Willow decide to investigate Gloria’s death, and what does this reveal about her state of mind?

Willow asks Lily about Gloria after learning that Lily’s father is the city clerk. She reasons that the clerk would have records of deaths on the island. This decision shows that Willow is no longer content to search for Jacob passively; she is now seeking answers about the island’s hidden history. It reveals her growing desperation and her willingness to dig into secrets, even if it means confronting uncomfortable truths.

2. How does the recommendation letter story illustrate Willow’s guilt and her motivation for helping others?

The story shows that Willow made a serious mistake as a teacher—writing a letter for the wrong student—which made her feel like a monster. She left teaching because of this failure. Her plan to apologize to Paige and her desire to help Lily stem from this guilt. She believes that helping one person might make things right, indicating that she is seeking redemption for her past error.

3. What role does the boombox man and his song play in the chapter?

The boombox man and his repeated song “Livin’ on the Edge” serve as a symbol of the island’s stagnation and Willow’s feeling of being trapped. When she asks why he plays it, he says it makes him feel good, which contrasts with Willow’s own sense of despair. The song becomes a motif for her inability to escape the island’s repetitive cycle, reinforcing her isolation and hopelessness.