Chapter 21: Twenty-One 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
The day before Austin leaves for his bachelor weekend in Jackson Hole, he and Katie bring her parents to dinner at the Fisher-Michaels home. Madeline forces herself to be pleasant, especially because Katie’s mother, Stacy Gallant, is impossible to be rude to. The evening is awkward and dull—Katie dismisses Madeline’s mention of a “Christmas wedding” and Mrs. Gallant presses about the bridesmaid dress, which is actually being repaired by Nana. Madeline lies that it’s at a bridal salon.
When her phone pings repeatedly with calls from Connor, Madeline escapes to take it. Connor reveals he and Lauren have broken up because she cheated on him with Robbie Nielson. He asks Madeline to come over and watch The Marvelous Mrs. Maisel. At his house, they talk on the basement couch. Connor admits he’d been waiting for something that wasn’t coming with Lauren. Madeline hesitates, then asks if he’s ever thought about them being together. He says yes. They acknowledge they’ve both wanted this but never made a move because one of them was always taken or uninterested in dating. They agree to give things a try, but Connor wants to wait a few days so their relationship isn’t tied to his breakup.
At Madeline’s club field hockey scrimmage the next Saturday, Connor shows up. She tells her teammates Connor is her boyfriend. Austin calls from the airport to congratulate her. Her parents lay down new rules about sleepovers and closed doors.
Their first official date is at Winberie’s Tavern near Princeton. While Connor is in the bathroom, Marco walks in with friends. He sees Madeline, pales, and leaves quickly. He texts her: “Please tell Connor hello for me. I’m really, really happy for you.” Later, on Madeline’s front porch, they have a playful good-night. Connor kisses her forehead and promises to sweep her off her feet.
The next morning, Madeline wakes late and heads downstairs to find Dad on the phone with Austin. Dad hangs up and tells her Austin is physically fine but shaken: Samira told him she’s in love with him.
Key Events
- Tense dinner with the Gallants and Katie; Madeline lies about the dress.
- Connor calls Madeline after breaking up with Lauren.
- Madeline and Connor confess their mutual romantic interest.
- They decide to wait a few days before starting a relationship.
- Madeline tells her teammates she and Connor are together.
- First date at Winberie’s Tavern; Marco appears briefly.
- Connor and Madeline share a sweet, playful good-night.
- Austin calls Dad after Samira confesses her love for him.
Character Development
Madeline grows bolder in pursuing what she wants. She initiates the confession with Connor and later tells her teammates the truth. Her lie about the dress shows she’s still avoiding confrontation with Katie, but she’s also protecting Nana’s efforts.
Connor reveals a vulnerable side. He’s honest about being hurt by Lauren’s cheating and admits he’s been waiting for something he can’t name. His decision to wait before dating Madeline shows maturity.
Austin’s phone call at the end shifts his arc dramatically. He’s “mentally shaken,” suggesting his engagement to Katie is now uncertain. Samira’s confession forces him to confront his own feelings.
Marco makes a brief but significant appearance. His text confirms he’s truly happy for Madeline and Connor, releasing any leftover tension from their past.
Themes, Symbols, or Motifs
Taking a leap. Madeline’s question—“Have you ever thought about what it would be like if we were together?”—mirrors her earlier bravery with Marco. She now applies that confidence to a relationship she truly wants.
Timing and patience. Connor wants to wait a few days to separate their start from his breakup. Madeline, who admits she’s not patient, agrees—showing growth.
Secrets and half-truths. Madeline lies about the dress to Mrs. Gallant, and she doesn’t tell Connor about her past crush on Marco. Both omissions create subtle tension.
“The girl next door.” Their joking about being the boy and girl next door reinforces the classic friends-to-lovers trope. Their relationship feels destined from the start of the book.
Love triangles (past and future). The chapter closes on a cliffhanger: Samira loves Austin. This threatens his engagement and Madeline’s newfound happiness, as Samira is her best friend and Austin her brother.
Why This Chapter Matters
Chapter 21 represents a turning point for Madeline and Connor. After chapters of tension and missed signals, they finally voice their feelings and agree to date. It also resets the romantic landscape: Marco is definitively out of the picture, and Madeline’s budding relationship is immediately contrasted with the Austin–Katie–Samira drama. The chapter raises the stakes for the rest of the novel by introducing a love triangle that implicates the whole family.
Study Questions
1. Why does Connor want to wait a few days before starting a relationship with Madeline?
He doesn’t want their new romance to be associated with his breakup with Lauren. He wants it to stand on its own, not as a rebound.
2. What does Madeline’s lie about the bridesmaid dress reveal about her character?
She avoids direct conflict with Katie and Mrs. Gallant. It also shows she’s willing to protect Nana and keep the dress drama private until it’s resolved.
3. How does Austin’s call at the end change the direction of the story?
Samira’s confession that she’s in love with Austin threatens his engagement to Katie and will likely cause turmoil among the friends and family. It also creates a potential conflict for Madeline, who is caught between her brother and her best friend.