Chapter 16 “Will”: Summary, Themes, and Character Analysis
⚠️ Spoiler Warning: This guide contains detailed spoilers for the entire novel. Proceed only if you've finished reading or are comfortable knowing the plot.
SummaryAfter the awkward end to their practice date, Will spends the rest of the day unable to shake the image of Annie's tearful smile. He searches for her at her house and Hank's before finding her at her flower shop, Charlotte's Flowers, even though it's closed. She's there working on a bouquet, clearly upset. He tells her he needs an apology bouquet for a woman he hurt. She admits she was embarrassed because she thought he was feeding her a line during their practice date. Will insists everything he said was true, including that he finds her sexy. She breaks down, revealing that no one has ever called her sexy; she's always seen as nice and kind, and her ex John called her boring and only “prettyish.” Will reassures her with a series of heartfelt compliments, even joking about murdering John. Then Annie proposes changing their arrangement: she wants him to be her all-encompassing practice someone, to help her take risks and discover who she is. They agree on a “time in/time out” cue to avoid confusion. They kiss, and it quickly becomes intense. Will carries her toward the storage room but stops himself, calling “time out.” She asks if it was okay; he says it was great. He takes a picture of her smiling. Later, walking her to her truck, he asks her favorite flower; she says magnolias.
Key Events- Will searches for Annie after work, checking her house and Hank's before finding her at her flower shop.
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He finds her working on a bouquet and asks for an apology bouquet for a woman he hurt.
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Annie explains she was embarrassed because she thought he was feeding her a line during their practice date.
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Will insists everything he said was true, including that he finds her sexy.
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Annie reveals she's never been called sexy; she's always seen as nice and kind, and her ex John called her boring and only “prettyish.”
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Will reassures her with compliments, including about her appearance and her personality.
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Annie proposes changing their arrangement: she wants him to be her all-encompassing practice someone to help her take risks and discover herself.
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They agree on a “time in/time out” cue to distinguish practice from real moments.
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They kiss, and it becomes intense; Will stops and calls “time out.”
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Annie asks if the kiss was okay; Will says it was great.
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Will takes a picture of Annie smiling.
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Later, walking her to her truck, Will asks her favorite flower; she says magnolias.
Character DevelopmentWill: He shows vulnerability by admitting he's not playing games with Annie, and he's spilling his heart out. He also demonstrates respect for boundaries by stopping the kiss and using the time-out cue. His desire to understand Annie and his fear of his own feelings are evident.
Annie: She reveals her insecurities about being seen as only nice and kind, not as a woman. She takes initiative by proposing a new arrangement and asking for practice kissing. She shows growth in trusting Will and being open about her feelings.
Themes, Symbols, or Motifs- Practice vs. real feelings: The line between practice and genuine emotion blurs as they kiss and Annie proposes a broader practice arrangement.
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Desirability vs. niceness: Annie's struggle with being seen as desirable rather than just nice.
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Boundaries and consent: The time in/time out cue establishes clear boundaries, and Will respects them by stopping.
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Self-discovery through practice: Annie wants to use Will as a guide to find herself.
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Vulnerability and honesty: Both characters open up about their fears and true feelings.
Why This Chapter MattersThis chapter is a turning point in Will and Annie's relationship. It moves from a practice dating arrangement to a more intimate and emotionally vulnerable connection. The kiss and the new terms they agree on set the stage for deeper romantic development. It also addresses Annie's self-esteem issues and Will's fear of real intimacy.
Study Questions and Answers1. How does the “time in/time out” cue change the dynamic between Will and Annie?
Answer: It provides a clear boundary to distinguish practice from real moments, allowing them to explore physical intimacy without confusion or hurt. 2. What does Annie's reaction to being called “sexy” reveal about her character?
Answer: It reveals her deep-seated insecurity about being seen as only nice and kind, not as a woman, and her past experiences with John have reinforced that. 3. Why does Will stop the kiss and call “time out”?
Answer: He realizes he's losing control and wants to respect the boundaries they just established, showing his commitment to consent and not rushing things.