Chapter 29 'Will': Summary and 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.

Summary

Will wakes up beside Annie and immediately admits he's scared of the intimacy between them. Annie, who was awake the whole time, teases him about it, joking that she's already called the pastor. Will confesses that last night felt meaningful and that meaningful scares him. He reveals he has a strict no-sleeping-over policy and is spiraling. Annie suggests what happened between them was friendship, which also freaks him out.

Will opens up about his past: he basically raised himself and his brother, and after leaving home, he decided to be selfish and enjoy freedom. No relationships, no expectations, no one to let him down. His job keeps him busy intentionally. Annie points out that he's now in her bed, a severe deviation from his plan. They both admit they have feelings for each other, but Annie says they're two people who caught feelings they were never supposed to have, on different life tracks. They agree to stay friends and pine for each other. Will says he should feel relief but instead feels frustrated.

Annie's phone buzzes with a text from Brandon Larsdale, the flower shop guy, asking if they're still on for their date that afternoon. Will's stomach sinks. Annie apologizes for not telling him sooner. Will tries to act normal but is filled with jealousy. He goes to the bathroom to compose himself, squeezing toothpaste across the wall in frustration. Annie follows him and explains: Brandon is a veterinarian who just moved to the neighboring town, came into the flower shop last week while Will was out of town, and asked for her number. She told him she wasn't looking for anything casual, and he said the same. She explains she has to get married—she has a gaping hole in her heart and this is the only thing left to try to close it, even though she's pretty sure it won't work.

Will tells Annie he's leaving soon after the wedding, claiming his boss approved his reassignment to Washington, D.C., and he accepted. In reality, he hasn't confirmed it yet—he was planning to ask for a few days to think about staying in Rome, but Annie's date is the kick he needed to remember their connection is fleeting. Annie sees through his lie and feels sad for him rather than hurt.

They role-play a first-date kiss as part of their dating-coach arrangement. Will paints a funny picture of a Little League date ending with a Capri Sun, and they laugh together before the kiss turns serious and passionate. Will pulls away, kisses her forehead, and leaves, telling her to enjoy her date.

Key Events

Will and Annie wake up together and both admit their mutual feelings.
They agree to stay friends because their life goals are incompatible.
Annie reveals her afternoon date with Brandon Larsdale, a veterinarian she met at the flower shop.
Will hides his jealousy and tells Annie he's leaving for Washington, D.C., after the wedding—a lie he hasn't actually confirmed.
They role-play a first-date kiss as part of their dating-coach arrangement.
Will leaves, feeling frustrated rather than relieved.

Character Development

Will — This chapter is a turning point for Will's emotional honesty. He admits he's scared of intimacy, reveals his past of raising himself and his brother, and confesses his deliberate choice to avoid relationships. His jealousy over Brandon is a new experience for him—he's never cared before if a woman he was seeing went out with another man. His decision to lie about accepting the D.C. reassignment shows his self-sabotage pattern: he'd rather flee than risk wanting something that scares him.

Annie — Annie continues to be emotionally honest and self-aware. She admits her feelings