Chapter 9: Annie — Summary, Themes, 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

The chapter opens with Annie making a dramatic entrance into Amelia's music studio, letter in hand, ready to confront her friend about the matchmaking scheme. She accuses Amelia of pulling a Funny Face on her—a reference to the film—and demands answers. Amelia, unapologetic and clearly pleased with herself, admits to the plan and immediately asks what Will said.

Annie withholds the answer, using the moment to tease Amelia by commenting on the studio decor instead. She notes the green velvet couch, the Audrey Hepburn poster, and suggests the room needs more plants. Amelia, growing impatient, tackles Annie in a hug. Annie resists at first but eventually gives in, blurting out that Will said yes. Amelia celebrates with a victory dance and finger guns, which Annie playfully disarms.

The conversation shifts to whether Will is the right person for this job. Annie compares him to Dick Avery, the Fred Astaire character from Funny Face, arguing that Will is an expert at playing the field rather than a wholesome romantic lead. She admits that Will feels dangerous to her and that she is more suited to someone like Fred Astaire. Amelia counters that Will's dating expertise is exactly what makes him perfect for the role—since Annie is not trying to marry him, his reputation is irrelevant. The arrangement is meant to help Annie get comfortable with dating, nothing more.

Amelia encourages Annie to voice her concerns. Annie claims she is worried the lessons will be embarrassing—that Will will laugh at her inexperience. Amelia reassures her that the arrangement is pressure-free and stringless, with no expectations on either side. Annie concedes that Amelia is right.

When Amelia asks whether Annie will tell her sisters, Annie immediately says no. This leads to a reflection on her relationship with Emily and Madison. Annie loves her sisters but feels they infantilize her, treating her as a sweet baby sister who is plain and unexciting. They reduce everything about her to that narrative, and she is tired of being placed in a box. Amelia, by contrast, sees her differently—she values Annie's opinion and understands her in a way her sisters never have. Annie feels closer to Amelia than to her own sisters, viewing her as both a sister and a close friend.

The chapter ends with Annie's internal confession of the real reason she wants to keep the arrangement secret. When Will's hand touched hers earlier, her entire body felt electrified. She breathed deeply when he had his arms around her, and play-fighting with him over the letter was the most fun she has had in perhaps her whole life. She is already clearly attracted to him and fears she will not be able to trust herself not to develop feelings over the coming weeks. She cannot tell Amelia any of this—Amelia might watch too closely, or worse, tell Will, who would pat her on the head like everyone else does. So she keeps the secret to herself, determined to squash any desire toward him on her own.

Key Events

Annie confronts Amelia about the matchmaking letter and the Funny Face plan
Amelia admits to the scheme and learns Will agreed to the arrangement
Annie and Amelia discuss Will's suitability as a dating tutor
Annie voices doubts about the lessons, claiming embarrassment as her main concern
Amelia reassures her the arrangement is pressure-free
Annie decides to keep the arrangement secret from her sisters
Annie privately acknowledges her attraction to Will and her fear of developing feelings

Character Development

Annie undergoes significant internal development in this chapter. Her outward confidence—the dramatic entrance, the teasing, the playful resistance to Amelia's hug—contrasts sharply with her inner vulnerability. She is aware of how her sisters perceive her and is actively pushing back against that narrative, even if only privately. Her decision to keep the arrangement secret is an act of independence, a refusal to let her family's perception define her. At the same time, her fear of developing feelings for Will reveals a deeper insecurity: she does not trust herself around him, and she is already anticipating the pain of an attraction she believes cannot be reciprocated in a meaningful way.

Amelia is shown as a supportive, understanding friend who sees Annie more clearly than Annie's own family does. She is unapologetic about her meddling but also genuinely invested in Annie's happiness. Her reassurance that the arrangement is pressure-free shows her emotional intelligence, even if she does not know the full extent of Annie's feelings.

Themes, Symbols, or Motifs

Family infantilization: Annie's reflection on her sisters reveals a central tension. Emily and Madison treat her as perpetually young—a sweet baby sister who is plain and unexciting—and this has shaped how Annie sees herself and how much she shares with them. Her secrecy is a direct response to being placed in a box.

Secrecy and independence: Annie's decision to keep the arrangement private is an act of self-determination. She wants to navigate this on her own, without her sisters' input, suggestions, or teasing. The secret also protects her vulnerability—she does not want anyone watching too closely.

Good girl/bad boy dynamic: The chapter explicitly references this narrative through Annie's imagined version of her sisters' reactions. Maddie would make crude jokes about the Bad Boy tutoring the Good Girl. Annie is tired of this narrative, yet she also cannot escape it—she describes Will as dangerously sexy and herself as more suited to someone like Fred Astaire.

Fear of developing feelings: Annie's internal confession is the emotional core of the chapter. She is not actually worried about embarrassment; she is worried about falling for Will. Her attraction is already physical and emotional, and she is trying to manage it alone.

Friendship as understanding: Amelia's role in Annie's life is contrasted with her sisters'. Amelia values Annie's opinion and understands her in a way her sisters never have. This friendship is the foundation that allows Annie to consider the arrangement at all.

Why This Chapter Matters

This chapter formally establishes the dating-lesson arrangement between Annie and Will, setting up the central premise of the book's second act. More importantly, it reveals Annie's internal conflict: she is attracted to Will and afraid of where that attraction might lead. The chapter also deepens the friendship between Annie and Amelia, positioning Amelia as the one person who sees Annie clearly. Annie's decision to keep the arrangement secret from her sisters creates narrative tension and stakes—she is risking her own emotional safety for a chance at independence.

Study Questions and Answers

1. Why does Annie decide not to tell her sisters about the dating lessons?

Annie keeps the arrangement private because her sisters infantilize her. They treat her as a sweet baby sister who is plain and unexciting, and they are overly opinionated about her life. She anticipates Emily making a list of reasons the plan will not work and Maddie making crude jokes about the Bad Boy tutoring the Good Girl. She is tired of that narrative and wants to navigate this on her own.

2. What is Annie's real fear about the dating lessons, and why does she hide it from Amelia?

Annie's real fear is that she will develop feelings for Will. She is already attracted to him—his touch electrified her, and play-fighting with him was the most fun she has had in perhaps her whole life. She hides this from Amelia because she is afraid Amelia will watch her too closely or tell Will, who would dismiss her attraction as cute the way everyone else does.

3. How does Amelia's understanding of Annie differ from her sisters'?

Amelia sees Annie as a close friend whose opinion she values, not as a child to be managed. She does not reduce Annie to a single narrative or tease her about her choices. This is why Annie feels closer to Amelia than to her own sisters, and why she is willing to trust Amelia's matchmaking plan in the first place.