Phoebe Berman's Gonna Lose It: 20-Question Book Quiz

This quiz spans the entire book, from the prologue to the epilogue. You'll face questions about plot points, character drives, thematic symbols, and big-picture synthesis. Mix of multiple-choice and short-answer formats. Ready to prove you know Phoebe's story inside out?

Want to dive deeper? Check out our book summary, questions and answers, and ending explained.

Quiz Questions

Plot / Sequence (8 questions)

What incident at age 12 causes Phoebe's lasting intimacy anxiety?
- a) A bee sting during a school assembly
- b) A panic attack and vomiting during a first kiss attempt with Lucas Johnson
- c) Falling off the stage in front of the whole school
- d) Getting lost at the mall with her friends
What is the name of Phoebe's therapist? (Short answer)
What item does Phoebe use to write her "How to Lose Your Virginity in Thirty Days" checklist?
- a) A label maker
- b) A purple felt-tipped marker
- c) A red pen from her desk
- d) A pencil from the bar
Who is the new fourth-grade teacher that Phoebe instantly decides she wants to lose her virginity to? (Short answer)
How does Phoebe discover that Jonathan has been going to Finn's apartment instead of Sydney's?
- a) Jonathan tells her directly
- b) She finds Finn's address on a receipt
- c) She uses the Find My Friends app and sees the location is Finn's apartment
- d) Meg accidentally reveals it at trivia night
What does Phoebe do immediately after finding Jonathan's green t‑shirt under Finn's bed?
- a) Confronts Finn at school
- b) Calls Matthew and apologizes
- c) Takes her first sick day and later throws away her romance novels
- d) Tells Alex about the discovery
During the wedding weekend, what does Phoebe's father tell her in the closet that helps her calm down?
- a) Her mother also had anxiety
- b) He once vomited from nerves on a date with her mother
- c) She should forget about the speech
- d) He will talk to Matthew for her
What major secret does Jonathan reveal when Phoebe apologizes to him after their fight?
- a) He is moving to San Francisco
- b) He is gay
- c) He has been dating Finn
- d) He is in love with Phoebe

Character Motivation (5 questions)

Why does Phoebe create the "How to Lose Your Virginity in Thirty Days" checklist?
- a) Her therapist Sandy assigned it
- b) Nora jokingly suggests the movie title, inspiring Phoebe to take action
- c) She wants to prove Jonathan wrong
- d) She finds a book with the same title at the library
Why does Matthew refuse to kiss Phoebe at Jamie's wedding? (Short answer)
Why does Phoebe resist her therapist's assignment to make an accomplishments list?
- a) She thinks listing accomplishments is counterproductive and insults the art of list-making
- b) She has no accomplishments to write down
- c) She doesn't trust Sandy's methods
- d) She lost the paper Sandy gave her
What motivates Phoebe to finally call Matthew after Jonathan comes out?
- a) She feels inspired by Jonathan's bravery and honesty
- b) She wants to ask him for a job reference
- c) She needs a date for the school Fall Ball
- d) She discovers Matthew has been texting Nora
Why does Jonathan keep his secret life hidden from Phoebe for so long? (Short answer)

Theme / Symbol (4 questions)

What does the "green t‑shirt" represent in the story? (Short answer)
What do the felt-tipped markers symbolize for Phoebe?
- a) Her love of crafting
- b) Her readiness for something truly important and her friendship with Meg
- c) Her OCD need for color-coding
- d) Her desire to redecorate her classroom
The recurring "crossword" motif in the novel primarily symbolizes:
- a) Competition between characters
- b) Communication and connection
- c) Boredom and routine
- d) Intellectual superiority
Which element most strongly conveys the theme of timeline pressure?
- a) The thirty‑day countdown list
- b) The letter from eighteen‑year‑old Phoebe demanding she lose her virginity
- c) Jamie's wedding
- d) All of the above

Synthesis (3 questions)

How does Phoebe's conversation with her father in the closet help her accept her anxiety? (Short answer)
Compare Phoebe's "list" coping strategy with Jonathan's secretive behavior. What does this contrast reveal about both characters? (Short answer)
In the epilogue, the therapist says, "everyone has their own virginities to lose." Explain what this means in the context of the novel. (Short answer)

Answer Key

b) A panic attack and vomiting during a first kiss attempt with Lucas Johnson.
Explanation: The prologue describes twelve‑year‑old Phoebe experiencing a panic attack and vomiting when Lucas touches her, which haunts her for seventeen years. (Prologue outline)
Sandy.
Explanation: Phoebe's therapist is consistently referred to as Sandy throughout the book.
b) A purple felt-tipped marker.
Explanation: In chapter 3, Phoebe uses a purple felt-tipped marker to write the title of her checklist. (Retrieved evidence chapter 5)
Finn.
Explanation: Phoebe meets Finn, the new fourth‑grade teacher, in chapter 6 and immediately decides he is the one she wants to lose her virginity to.
c) She uses the Find My Friends app and sees the location is Finn's apartment.
Explanation: In chapter 20, Phoebe tracks Jonathan's phone and discovers the location matches Finn's apartment after finding the green t‑shirt.
c) Takes her first sick day and later throws away her romance novels.
Explanation: Chapter 21 shows Phoebe taking her first sick day ever, lying in bed, and then throwing away all her romance novels and the list.
b) He once vomited from nerves on a date with her mother.
Explanation: In chapter 14 (wedding chapter), Phoebe's father shares his own pre‑date anxiety story, normalizing her feelings. (Retrieved evidence chapter 16)
b) He is gay.
Explanation: In chapter 22, Jonathan comes out to Phoebe, revealing he used a secret app to meet men.
b) Nora jokingly suggests the movie title, inspiring Phoebe to take action.
Explanation: Chapter 3 shows Nora saying "How to Lose Your Virginity in Thirty Days" as a joke, which sparks Phoebe's idea. (Retrieved evidence chapter 5)
Because Phoebe is intoxicated.
Explanation: In chapter 14, Matthew refuses to kiss her because she is drunk. (Retrieved evidence chapter 16)
a) She thinks listing accomplishments is counterproductive and insults the art of list-making.
Explanation: In chapter 1, Phoebe tells Sandy that the assignment is "an insult to the art of list making." (Retrieved evidence chapter 3)
a) She feels inspired by Jonathan's bravery and honesty.
Explanation: After Jonathan comes out, Phoebe calls Matthew, drawing a parallel between his courage and her own fear. (Chapter 23 outline)
He is afraid to come out as gay and fears losing Phoebe's friendship if the secret gets out.
Explanation: Chapter 22 reveals that Jonathan was living two lives, using a secret app, because he was scared of being too late and of losing his best friend.
It symbolizes Jonathan's secret life and the betrayal of trust between him and Phoebe.
Explanation: The green t‑shirt under Finn's bed is the clue that forces Phoebe to realize Jonathan has been seeing Finn.
b) Her readiness for something truly important and her friendship with Meg.
Explanation: The markers were a gift from Meg and Phoebe saves them for a life‑altering project, symbolizing hope and her bond with Meg. (Retrieved evidence chapter 3)
b) Communication and connection.
Explanation: Crosswords are a bonding activity for Phoebe with Jonathan and later with Matthew; they represent shared understanding and intimacy.
d) All of the above.
Explanation: The thirty‑day list, the letter, and Jamie's wedding all reinforce the pressure Phoebe feels about turning thirty without having lost her virginity.
He shares his own story of pre‑date anxiety, telling her that anxiety is normal and that there is nothing wrong with her. (Chapter 14 outline, retrieved evidence chapter 16)
Phoebe uses external planning and control (the list) to manage her fear, while Jonathan hides his true self out of shame. Both avoid vulnerability but eventually learn that honesty and self‑acceptance are the only ways forward. (Synthesis of chapters 3, 17, and 22)
It means that everyone has fears or first‑time experiences they must face, not just sexual virginity. Self‑acceptance and the courage to try are what truly matter. (Epilogue outline)