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Quick answer: Good book club questions for City of Girls focus on freedom, shame and women's choices. Below are 17 questions grouped by theme, with a spoiler-free summary, a characters-and-themes table, meeting ideas and a sample 90-minute plan.
Quick facts
– Book: City of Girls by Elizabeth Gilbert
– First published: 2019
– Setting: 1940s New York City, with an epilogue years later
– Content note: Sexual content, alcohol and a public scandal
City of Girls is a rewarding choice for a book club because it gives readers plenty to discuss without needing special knowledge. This guide gives you questions you can use as written or adapt for your group, plus ideas for running the meeting, so that a host with little time can still lead a good conversation.
Table of Contents
Spoiler-Free Summary
In 1940, nineteen-year-old Vivian Morris is sent to live with her Aunt Peg in New York City after flunking out of Vassar. Peg owns the Lily Playhouse, a run-down theatre in Midtown, and Vivian throws herself into its world of showgirls, costumes and nightlife. When she makes a mistake that leads to a public scandal, her life changes direction. Told by Vivian decades later, the novel is a celebration of female friendship, independence and second chances.
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Main Characters and Themes
| Character or Theme | What to Know |
|---|---|
| Vivian Morris | The narrator, a young seamstress who comes to New York |
| Aunt Peg | Owner of the Lily Playhouse |
| Celia Ray | A glamorous showgirl and Vivian's wild friend |
| Olive | Peg's loyal, practical assistant |
| Frank | A man Vivian meets later in life |
Discussion Questions (Contains Spoilers)
These questions assume everyone has finished the book, so they discuss the ending. They are grouped by theme so you can move through them in order or jump to the topic your group cares about most. Feel free to rephrase them, add follow-up questions such as “why do you think so?” and skip any that do not suit your members.
Opening Reactions
- What was your first impression of City of Girls, and did it change as you read?
- Which scene or passage stayed with you most, and why?
Vivian's New York
- How does New York change Vivian?
- Which scene at the Lily Playhouse did you enjoy most?
- What did you think of Celia Ray?
- How does Vivian use her sewing talent?
Scandal and Shame
- How did you react to the scandal?
- Was Vivian treated fairly afterwards?
- How does the book handle shame and forgiveness?
- Which character showed the most loyalty?
Looking Back
- Who is Vivian writing to, and why does it matter?
- What did you think of her friendship with Frank?
- Does Vivian live a happy life?
- What does the book say about women's freedom?
Looking Back
- How did the ending of City of Girls make you feel, and was it the ending you expected?
- Would you recommend this book to a friend, and what would you tell them first?
- If you could ask Elizabeth Gilbert one question, what would it be?
Meeting Ideas
Dress in 1940s style or serve classic cocktails and mocktails, and play big-band music in the background.
A simple way to start is to have each person share a one-sentence rating of the book before discussion begins. It surfaces disagreements early and gives quieter members a chance to speak first. You can also ask each member to bring one question of their own, which often leads to the best conversations of the night.
Ways to Make the Discussion Richer
- Compare formats. If a film, series or stage version of City of Girls exists, discuss what changes and why.
- Share a favorite line. Ask each person to read a short passage that stood out and explain what it meant to them.
- Cast the book. Ask the group who they would cast in the main roles, and why.
- Rate the pace. Ask where the book felt fastest or slowest, and whether the structure worked for them.
- Pair it with a snack or drink. Food connected to the story gives guests something to talk about before the formal discussion starts.
Tips for Leading the Discussion
- Prepare, but stay flexible. Pick a handful of questions in advance and let the group's reactions guide you.
- Invite quieter voices. Ask someone who has not spoken to share a favorite line or scene.
- Welcome disagreement. A lively debate about a character is a sign that the book is working.
- Return to the text. Ask members to point to a passage in City of Girls that supports their view.
- Watch the clock. Move on when a question has run its course, and save extra questions for another time.
If your group has only an hour, choose one question from each theme and skip the rest.
Is City of Girls a Good Book Club Pick?
City of Girls is fun, glamorous and full of discussion about women's choices, a great pick for lively groups.
Books Like This One
- Rules of Civility by Amor Towles: a young woman in 1930s Manhattan
- The Seven Husbands of Evelyn Hugo by Taylor Jenkins Reid: an aging film star reveals her life
How to Structure Your Meeting
A 90-minute meeting works well in four parts:
- Welcome and quick ratings (10 minutes). Settle in and share a one-line reaction.
- Spoiler-free talk (20 minutes). Start with characters, setting and style before the plot.
- Spoiler discussion (45 minutes). Work through three or four of the questions above, letting the conversation wander when it is productive.
- Wrap-up (15 minutes). Share favorite lines, choose the next book and thank the host.
If the conversation is going well, it is fine to let it run long and skip some questions.
After the Meeting
Send a short follow-up message with the next title, the date and a link to any readings or articles that came up. Some groups keep a simple record of books read and ratings, which makes it easier to choose future picks and spot the kinds of books the group loves most.
Frequently Asked Questions
How many questions should we prepare for City of Girls?
Five to eight is enough for a 90-minute meeting. This guide gives seventeen, so you can choose the ones that fit your group.
Does City of Girls work as a first pick for a new book club?
City of Girls is fun, glamorous and full of discussion about women's choices, a great pick for lively groups.
Is City of Girls a true story?
No, it is fiction, though it captures the real theatre world of 1940s New York.
Does it have mature content?
Yes, it includes frank sexual content.
Are there spoilers in this guide?
The questions after the summary discuss the ending.
What if some members have not finished City of Girls?
Start with the spoiler-free questions and a short plot recap, then move to the spoiler section only when most people have finished.