Rewind It Back Quiz: 20 Questions to Test Your Memory of the Story
Think you know every detail of Rio and Hallie's second-chance romance? This 20-question quiz spans the entire book—from childhood flashbacks to the epilogue proposal. Answer each question, then check the key below to see how you score.
For deeper discussion, visit the Rewind It Back book page, the Questions and Answers, or the Ending Explained.
Quiz Questions
Plot / Sequence (Questions 1–8)
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What forces Hallie to leave her date with Brian at the hockey game?
- A) Brian’s phone shows a contact named “Diamond Ring Emoji.”
- B) Rio scores a hat trick.
- C) Hallie gets a call from her father.
- D) The game ends early.
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Where does Rio first see Hallie after six years apart?
- A) At the grocery store.
- B) At Wren’s mailbox.
- C) At the United Center during a Raptors game.
- D) At the design firm.
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How does Rio learn that Hallie is the interior designer he hired?
- A) His mother tells him.
- B) Hallie shows up at practice.
- C) He sees her car in Wren’s driveway and confronts her.
- D) A teammate introduces them.
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What does Hallie find in Rio’s closet that proves he never forgot their past?
- A) A box of old mixtapes and a friendship bracelet.
- B) A framed photo of them.
- C) A letter he wrote.
- D) A hockey jersey with her name.
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Why does Hallie drop out of college and move to Minnesota?
- A) To follow a boyfriend.
- B) To take a job.
- C) To care for her father after his cancer diagnosis.
- D) To escape Rio.
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What secret does Hallie discover about her mother and Rio’s father?
- A) They had an affair.
- B) They were business partners.
- C) They planned a surprise party.
- D) They were secretly married.
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How does the rift between Rio’s mother and Hallie finally heal?
- A) Rio begs his mother.
- B) Hallie travels to Boston and confronts Mrs. DeLuca.
- C) Rio’s father intervenes.
- D) They never fully reconcile.
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In the epilogue, what plan does Rio reveal to his friends?
- A) He is moving to Boston.
- B) He bought a new house.
- C) He plans to propose on the roof.
- D) He is adopting a dog.
Character Motivation (Questions 9–13)
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Why does Rio initially fire Hallie as his designer?
- A) He doesn’t like her design style.
- B) He can’t bear to see her every day because of their painful history.
- C) He wants to hire a more famous designer.
- D) He is moving to Boston immediately.
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Why does Hallie work five night shifts as a bartender in addition to her design internship?
- A) She enjoys the social life.
- B) She needs extra income to pay off debt from her father’s medical bills.
- C) She wants to avoid Rio.
- D) Her design firm requires it.
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Why does Rio decide to stay in Chicago instead of signing with Boston?
- A) He gets a better contract offer.
- B) He wants to be with Hallie.
- C) His mother pressures him.
- D) He hates Boston.
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Why does Hallie keep her father’s cancer and her mother’s affair secret from Rio for six years?
- A) She was ashamed of her family.
- B) She wanted to protect her father and Rio from the truth.
- C) She didn’t think it mattered.
- D) Rio never asked.
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Why does Rio keep a boombox and old mixtapes?
- A) He is nostalgic for the 1990s.
- B) They are the only things that remind him of his childhood.
- C) They are emotional anchors to his memories with Hallie.
- D) He uses them for hockey warm-ups.
Theme / Symbol (Questions 14–17)
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What does the phrase “rewind it back” primarily symbolize?
- A) The desire to erase mistakes.
- B) The ability to relive cherished memories.
- C) A literal time machine.
- D) A hockey play.
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What does the shared roof between Rio’s and Hallie’s houses represent?
- A) Their physical proximity.
- B) Their secret meeting place and emotional sanctuary.
- C) A dangerous area.
- D) A place to watch hockey games.
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Rio’s jersey number 38 is Hallie’s birthday. What does this number symbolize?
- A) His lucky number.
- B) His commitment to Hallie even when they were apart.
- C) His age.
- D) His draft position.
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How does the author use music throughout the novel? (Short answer)
(Write 1–2 sentences.)
Synthesis (Questions 18–20)
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How does the theme of found family in Rewind It Back connect to the larger Windy City series? (Short answer)
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Compare the ways Hallie and Rio both sacrifice for others. (Short answer)
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In what way does the boombox serve as a symbol for both nostalgia and reconciliation? (Short answer)
Answer Key
Multiple-Choice Answers
| Q | Answer | Explanation |
|---|---|---|
| 1 | A | Hallie spots a “diamond ring” emoji contact on Brian’s phone, revealing he is married. (Outline Chapter 4) |
| 2 | C | Rio sees Hallie in the crowd after checking a player into the glass at the United Center. (Outline Chapter 4) |
| 3 | C | Rio recognizes Hallie’s car in Wren’s driveway and confronts her; she confirms she is the designer. (Outline Chapter 4) |
| 4 | A | Hallie finds a box containing every mixtape and CD she gave him and a torn friendship bracelet. (Outline Chapter 24) |
| 5 | C | Hallie drops out to care for her father after his non‑Hodgkin lymphoma diagnosis. (Outline Chapter 28) |
| 6 | A | Hallie walks in on her mother exiting Mr. DeLuca’s bedroom half‑dressed. (Outline Chapter 41) |
| 7 | B | Hallie flies to Boston, explains her silence, and reconciles with Mrs. DeLuca. (Outline Chapters 40–42) |
| 8 | C | Rio shows his engagement ring to his friends and says he will propose on the roof. (Outline Epilogue) |
| 9 | B | Rio admits he cannot face Hallie every day; the history is too painful. (Outline Chapter 5) |
| 10 | B | She is in debt from covering her father’s cancer trial expenses. (Outline Chapters 11, 29) |
| 11 | B | The last song on his relationship playlist marks his decision to re‑sign with Chicago for Hallie. (Outline Chapters 43–45) |
| 12 | B | Hallie feared that the truth would “destroy her already ill father” and hurt Rio. (Outline Chapter 41) |
| 13 | C | The boombox and tapes preserve their shared memories; Rio kept them to hold on to Hallie. (Outline Chapters 5, 29) |
| 14 | B | Hallie picks a song to “rewind it back” and relive significant moments. (Outline Chapter 3) |
| 15 | B | The roof is where they had private conversations, gave each other mixtapes, and eventually reaffirmed their love. (Outline Chapters 7, 12, 22, 45) |
| 16 | B | The number 38 is Hallie’s birthday; picking it was a private vow to her even when they were estranged. (Outline Chapter 38) |
Short-Answer Explanations
17. How does the author use music throughout the novel?
Music functions as an emotional language that ties the characters together. Hallie’s childhood habit of assigning a song to each memory (the “rewind it back” concept) and Rio’s relationship playlist create a timeline of their love, communicating longing, regret, and hope when words fail.
18. How does the theme of found family in Rewind It Back connect to the larger Windy City series?
The novel features Rio’s friend group—Indy, Ryan, Zee, Stevie, Miller, Kai, Kennedy, Isaiah—who all found their own romances in earlier Windy City books. By integrating Hallie into this circle, the story reinforces the series’ central message that love and support come from the family we choose.
19. Compare the ways Hallie and Rio both sacrifice for others.
Hallie sacrifices her college dreams and financial stability to care for her father through his cancer treatment. Rio sacrifices a lucrative contract with Boston and a return to his hometown to stay in Chicago with Hallie; he also pays off her student loans to relieve her burden. Both put the well‑being of a loved one above their own ambitions.
20. In what way does the boombox serve as a symbol for both nostalgia and reconciliation?
The boombox represents the past they shared: Rio kept it and all of Hallie’s mixtapes for six years, proving he never forgot her. When they use it again together—playing music, laughing about old songs—it becomes a tool for rebuilding trust and “rewinding” their relationship, allowing them to start fresh while honoring their history.
Want more? Check the full book page for a summary, or head to Questions and Answers and Ending Explained for deeper analysis.