Chapter 20: Annie — Summary and Study Notes
⚠️ 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
Late on a summer night, Annie hears a tapping at her bedroom window. Peeking through the curtains, she finds Will Griffin outside, motioning for her to let him in. Surprised and flustered—she's wearing her banana-print pajamas—she unlatches the window and he climbs through with surprising ease. He immediately notices her sleepwear, and she explains that her siblings call her Anna-banana, a nickname that has inspired an entire drawer of banana-themed pajamas. Will, with unusual seriousness, asks her to promise she'll never stop wearing them, and she agrees, feeling oddly comforted by his request.
Will admits he didn't know which room was hers; he gambled on the only lit window and would have pretended to be drunk if he'd stumbled into a sibling's room. He then notices a framed photo on her dresser—the last picture ever taken of her family before her parents died. He offers a quiet apology, and when Annie tries to brush it off, he pulls her into a hug and kisses her forehead. She's overwhelmed by the tenderness, especially since she's used to being the comforter in her family, not the one being comforted.
Will explains he's leaving town with Amelia for a few days for work and realized he didn't have Annie's phone number. She enters it into his phone, and he changes the contact name from Annie Walker to Annabell, sending a flutter through her. He then makes himself at home on her bed, and when he picks up the historical romance novel she left open, he begins reading the steamy scene aloud, teasing her mercilessly. Annie, mortified, tackles him to retrieve the book, and in the struggle, she ends up straddling him—a moment that leaves both of them breathless and acutely aware of the physical tension between them.
Key Events
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Will appears at Annie's window at ten o'clock at night and climbs into her room.
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He comments on her banana-print pajamas and asks her to promise she'll keep wearing them.
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Will admits he didn't know which room was hers and would have pretended to be drunk if he'd found a sibling's room.
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He notices the last family photo taken before her parents died and offers sympathy, then hugs her and kisses her forehead.
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Will tells Annie he's leaving town with Amelia for work and asks for her phone number.
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He changes her contact name to Annabell, which delights her.
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Will stays to hang out, picks up her romance novel, and reads the steamy passage aloud.
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Annie tackles him to get the book back, and they end up in a compromising position with her straddling him.
Character Development
Annie
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This chapter reveals Annie's deep-seated role as the family comforter. She explains that she chose this role as a child to lessen her siblings' pain after their parents died, but as a result, she rarely receives comfort herself. Will's hug and forehead kiss are a rare moment of being cared for, and she's both moved and confused by it.
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Her vulnerability is on full display: she's nervous about Will being in her room, admits she's not good at socializing or secret late-night meetings, and struggles to express her feelings. Yet she also shows courage by asking him to stay and by physically going after the book, even if it leads to an awkward position.
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The banana pajamas and the nickname Anna-banana are part of her identity. Will's insistence that she never change that part of herself signals that he accepts her as she is, which helps her relax around him.
Will
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Will's actions show a softer, more thoughtful side. He goes out of his way to get her phone number before leaving town, and he's gentle when he sees the family photo, offering comfort without prying. His hug and forehead kiss are tender and unexpected.
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He's also playful and teasing, as seen when he reads her romance novel aloud and jokes about the pirate's lack of consent. But he's careful to check in with her, asking if she's uncomfortable and offering to leave if she wants him to.
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His comment about the consent red flags in the book shows a modern, respectful attitude, which contrasts with his rough exterior.
Themes, Symbols, or Motifs
Grief and Parental Loss
The family photo is a powerful symbol of Annie's loss. She was only three when her parents died, and she's spent her life trying to ease her siblings' pain while burying her own. Will's simple acknowledgment that it must still hurt—and his decision to hold her instead of asking questions—allows her to feel seen without having to articulate her grief.
Comfort Without Words
Will's hug and forehead kiss are acts of comfort that don't require explanation. This contrasts with Annie's usual role of providing comfort to others. The chapter emphasizes that sometimes presence and physical touch are more healing than conversation.
Vulnerability and Emotional Walls
Annie has built walls to protect herself from expressing her own needs. She admits she's not good at socializing or letting people in. Will's persistence and gentle approach begin to chip away at those walls, as seen when she asks him to stay and later when she's willing to be physically close to him.
Physical Intimacy and Tension
The chapter is charged with physical awareness—from Will's thumb brushing Annie's wrist to the final moment when she's straddling him. This tension is both exciting and frightening for Annie, who isn't used to such closeness. The scene also highlights the difference between fictional romance (the book) and real-life intimacy, which is messier and more complicated.
Nicknames and Identity
The nickname Anna-banana and Will's decision to call her Annabell in his phone are small but significant. They show how names can create intimacy and a sense of belonging. Will's insistence that she keep her banana pajamas reinforces that he values her authentic self.
Consent in Romance Fiction
Will's commentary on the pirate's assumption that the heroine wants him—and his statement that a man should never assume—brings a modern, consent-aware perspective into the story. This moment also serves as a contrast to his own behavior, as he's careful to ask Annie if she's comfortable and offers to leave.
Why This Chapter Matters
This chapter is a turning point in Annie and Will's relationship. It moves them from a tutor-student dynamic to something more personal and intimate. Will's late-night visit, his vulnerability in admitting he didn't know her room, and his tender response to her family photo all show that he sees her as more than just a client. For Annie, the chapter forces her to confront her own emotional walls and her fear of being cared for. The physical tension that builds throughout the scene—culminating in the straddling moment—sets the stage for the romantic development that will follow. It also deepens our understanding of Annie's backstory and the reasons she's so guarded, making her a more sympathetic and relatable character.
Study Questions and Answers
1. How does Will's reaction to the family photo demonstrate his understanding of Annie's grief?
Will doesn't offer platitudes or ask probing questions. Instead, he acknowledges that the loss must still hurt, then pulls Annie into a hug and kisses her forehead. This shows he understands that sometimes people need comfort rather than conversation. His actions contrast with Annie's usual role as the comforter, and they allow her to receive care without having to explain herself.
2. What does the banana pajamas promise symbolize in the context of Annie's identity?
The banana pajamas are a quirky, personal part of Annie's identity, tied to her nickname and her family. Will's request that she promise never to stop wearing them signals that he accepts her fully, including the parts she might feel self-conscious about. The promise becomes a symbol of his affection and his desire for her to remain true to herself, even as she grows and changes.
3. How does the book-reading scene highlight the differences between fictional romance and real-life intimacy?
The scene is comedic, but it also underscores a key theme: the book's dramatic, over-the-top romance is a fantasy, while the real tension between Annie and Will is awkward, uncertain, and genuine. Will's commentary on consent in the book shows his modern, respectful attitude, which contrasts with the pirate's assumptions. The physical struggle that ends with Annie straddling him is a far cry from the polished scenes in her novel, emphasizing that real intimacy is messy and requires communication.