Chapter 21 Summary: Annie

⚠️ 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 and Will on her bed, the earlier playfulness fading into something more serious. Annie notices that Will's tattoos extend past his bicep and asks to see them. Will gives his permission, and Annie slowly pushes up his shirt, discovering inked foliage across his chest. Will sits up and removes his shirt entirely, and Annie touches his skin, marveling at the texture of his tattoos.

Will then asks if she is a virgin. Annie confirms, explaining that she has waited because she has never felt safe enough with anyone to share that part of herself. She reflects on how her siblings have made her feel like her virginity was about being sweet or holy, but Will doesn't judge her. He seems to understand that it has always been about protecting herself emotionally.

Will asks if she wants to continue, using the phrase time in, and Annie agrees. He tells her she can take as much as she wants and that he will keep his hands on her hips unless she tells him to move them. Annie gives him permission to move his hands.

They kiss with increasing intensity. Annie realizes she wants passion, not just what she describes as nice and soft and stable. She asks Will to be less controlled, and he responds with a more demanding kiss. She discovers his tattoos wrap over his shoulder onto his back, something she has been wondering about every night since she met him.

As Will begins unbuttoning her shirt, Annie calls time out and says she is not ready. Will stops immediately, tells her she owes him nothing, and says that just kissing her is a gift. She sees fear in his eyes, something raw she never expected. He pulls her to rest her head on his chest, holding her tightly.

Key Events

Annie asks to see Will's tattoos and discovers they extend across his chest and over his shoulder onto his back.
Will asks if Annie is a virgin; she confirms and explains she has waited because she never felt safe enough.
They establish a time in/time out consent system.
Annie gives Will permission to move his hands, and they kiss with growing intensity.
Annie asks Will to be less controlled, and he responds passionately.
Annie calls time out when Will begins unbuttoning her shirt.
Will stops immediately, reassures her she owes him nothing, and holds her against his chest.

Character Development

Annie

This chapter marks a turning point for Annie. She admits her virginity out loud for the first time and articulates why she has waited, not because she is sweet or holy as her siblings imply, but because she has never felt safe enough. She confronts her own desires, realizing she wants passion alongside stability. She also demonstrates agency by calling time out when she is not ready, showing that her self-discovery includes honoring her own boundaries.

Will

Will shows remarkable patience and respect throughout the chapter. He asks before acting, waits for explicit permission, and stops immediately when Annie calls time out. His reassurance that she owes him nothing reveals his care for her emotional wellbeing. The fear in his eyes at the end hints at deeper feelings or vulnerabilities he has not yet shared.

Themes, Symbols, or Motifs

Consent and boundaries: The time in/time out language is a clear, mutual system. Will asks before touching, waits for permission, and stops instantly when Annie says stop.
Vulnerability and trust: Annie's admission about her virginity and why she has waited is a major act of trust. Will's response, without judgment, deepens that trust.
Tattoos as symbols: Annie's obsession with where Will's tattoos end represents her curiosity about the hidden parts of him, and perhaps about the hidden parts of herself.
Reputation vs true self: Annie's internal conflict between being sweet Annie Walker and her actual desires.
Desire vs stability: Annie's realization that she wants both passion and stability, and her fear that with Will she can only have passion.
Temporary relationship: Annie's awareness that Will won't be there forever colors her decision to take this risk.

Why This Chapter Matters

This is a pivotal chapter for Annie's character arc. She confronts her own desires, articulates her reasons for waiting, and takes agency in a sexual situation, both by initiating and by stopping when she is not ready. Will's response models healthy consent and emotional safety. The chapter also plants seeds for future conflict: Annie's awareness that Will is temporary, and the fear she sees in his eyes.

Study Questions and Answers

Why does Annie say she has been waiting to have sex?

Annie explains she has waited because she has never felt safe enough with anyone to share that part of herself. It is not about proving she is sweet or holy as her siblings imply, but about protecting herself emotionally.

How does the time in/time out system function in this chapter?

Will asks time in before proceeding, and Annie agrees. Later, when she is not ready, she calls time out and Will stops immediately. The system gives Annie control and ensures consent is ongoing and revocable.

What does Annie's reaction to Will's tattoos reveal about her?

Annie has been wondering about where Will's tattoos end every night since she met him. Her fascination represents her curiosity about the hidden parts of him, and her willingness to explore the unknown, both in him and in herself.