City of Girls Book Club Questions

City of Girls isn’t another memoir from Elizabeth Gilbert, but it kind of reads like one. The book’s themes of female friendship, sexual freedom and finding oneself are all set in the glittering theater district of 1940’s New York City. The range of characters and the lead character’s own personal journey are what will make City of Girls an interesting book club read.

This guide is designed to provide you with City of Girls book club questions and additional fodder for your discussion.

If you are new here, our discussion guides have four sections. The first is the publisher synopsis. This alone can provide a start for your City of Girls book club discussion. Is the synopsis accurate? Would you have written it differently?

The second section gives you 10 specific City of Girls book club questions to help you get the conversation started. The third has a range of reviews about the book (some are good, some are “meh”). You can use these to further stimulate conversation.

And if you liked the book, the final section with give you three suggestions for related reads.

City of GirlsBook Club Questions- cover

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City of Girls Synopsis

(We always chose to provide the publisher synopsis because we feel that it’s worthwhile to discuss whether the official book description actually squared with your experience of the book.)

City of Girls, by Elizabeth Gilbert

“Life is both fleeting and dangerous, and there is no point in denying yourself pleasure, or being anything other than what you are.”

Beloved author Elizabeth Gilbert returns to fiction with a unique love story set in the New York City theater world during the 1940s. Told from the perspective of an older woman as she looks back on her youth with both pleasure and regret (but mostly pleasure), City of Girls explores themes of female sexuality and promiscuity, as well as the idiosyncrasies of true love.

In 1940, nineteen-year-old Vivian Morris has just been kicked out of Vassar College, owing to her lackluster freshman-year performance. Her affluent parents send her to Manhattan to live with her Aunt Peg, who owns a flamboyant, crumbling midtown theater called the Lily Playhouse. There Vivian is introduced to an entire cosmos of unconventional and charismatic characters, from the fun-chasing showgirls to a sexy male actor, a grand-dame actress, a lady-killer writer, and no-nonsense stage manager.

But when Vivian makes a personal mistake that results in professional scandal, it turns her new world upside down in ways that it will take her years to fully understand. Ultimately, though, it leads her to a new understanding of the kind of life she craves – and the kind of freedom it takes to pursue it. It will also lead to the love of her life, a love that stands out from all the rest.

Now eighty-nine years old and telling her story at last, Vivian recalls how the events of those years altered the course of her life – and the gusto and autonomy with which she approached it. “At some point in a woman’s life, she just gets tired of being ashamed all the time,” she muses. “After that, she is free to become whoever she truly is.” Written with a powerful wisdom about human desire and connection, City of Girls is a love story like no other.

City of Girls Book Club Questions

These questions have been tailored to this book’s specific reading experience, but if you want more ideas, we also have an article with 101 generic book club questions.

  1. Vivian tells her life story in the form of a letter to Angela. Gilbert actually referred to the book as “my fourth memoir”. What do you think of this memoir-as-fiction device and how might the book have read differently if it was written in a linear timeline?
  2. The opening page quotes Colette “You will do foolish things, but do them with enthusiasm.” What did you find to be some of Vivian’s more enthusiastically foolish acts?
  3. Conversely, Olive is relentlessly practical, even a gloomy killjoy at times. “Be careful, Olive”, says Billy. “Make sure you don’t enjoy a minute of our success.” How was her character necessary to the story? Did you relate to Olive?
  4. The scene in which Edna dresses down Vivian for the tryst with Celia and Arthur is positively devastating. Edna accused Vivian of being a pretty nobody…boring. Yet in Vivian’s later years, she also came to describe herself as “and old battle-ax who would rather stand dry-eyed and undefended in the most hostile underbrush of truth than degrade herself and everyone else by collapsing into a swamp of manipulative tears”. Was the battle-ax in Vivian all along? Or did Edna trigger something?
  5. The book had a lot more sex than one might have imagined for the ’40’s. Gilbert interviewed a lot of theatre people from the era, including a 90 year old former show girl. “When I asked her, did you ever regret never getting married, she said, “Who the hell wants to f— the same man for 60 years?” What did you think of the sexual action in the book?
  6. The book seems to celebrate a certain “can-do” spirit of the 1940’s and the war. What of that spirit has America retained and what has it lost?
  7. Female friendship plays such an important role in City of Girls. Discuss the relationship between Vivvie and Celia and also the relationship between Vivvie and Marjorie. Or perhaps even Peg and Olive’s relationship.
  8. Vivian’s relationship with Frank is a major twist. Did you see it coming? Who did you imagine Angel’s father to be?
  9. Have you ever been to the theater in NYC? If so, how was your experience relative to Gilbert’s Times Square of the ‘40’s?
  10. At 469 pages, City of Girls is no short read. How did you find the pacing?

Selected Reviews for City of Girls

(Use these selected Goodreads reviews to compare with your own experience of the book. Do you agree or disagree with the reviews?)

“…When the second half takes a more serious turn, it’s a little disappointing. Everything was so wonderful! Why did you have to ruin it? The answer, of course, is that real life isn’t all fun and feathers. Gilbert succeeds in the grittier sections by showing us that, even in the realm of adult consequences, it’s possible to move beyond mistakes, be true to yourself, and ultimately live a fabulous life.”

“1) Elizabeth Gilbert has an excellent publicist.
2) Have sex and be happy.
3) Nothing happens during the first 50%. Then, there is mild drama, followed by more nothingness. And, it ends on a somber note.”

“It manages to be a fun, fast read, while also grappling with big messy issues like shame, grief, and how we live with our choices and mistakes.”

“Who else would love to see a spinoff book from Celia’s perspective? I am dying to find out what happened to her!”


Use our guide to find dozens of book ideas for your group.

More Books Like City of Girls

If you like a strong independent woman who knows her own mind, then check out our discussion guide and related reads for Things in Jars, Matrix and Erotic Stories for Punjabi Widows.

Themes of feminism, friendship and finding (and expressing) your authentic self play out in City of Girls. If you liked that, then you (and your book club) may like the following books like City of Girls.

The Seven Husbands of Evelyn Hugo book cover

The Seven Husbands of Evelyn Hugo, Taylor Jenkins Reid

After decades of serving the public, Evelyn Hugo decides that it’s time to serve herself. She’s ready to tell the truth about her glamorous and scandalous life…and who was her true family. Because (spoiler) it kinda wasn’t her husbands. She reaches out to an unknown magazine reporter Monique Grant for the job, and no one is more astounded than Monique herself.

“The journey through Evelyn Hugo’s life is filled with trials and tribulations, love and loss, mistakes and redemption.”

If you read it, then check out our Evelyn Hugo book club guide ( with spoilers). We’ve also got a list of books like Evelyn Hugo, which features City of Girls and other great reads.

Girl Woman Other book cover

Girl, Woman, Other, Bernardine Evaristo

This book won the Booker Prize in 2019. It follows the lives of 12 Black women in contemporary Britain. The book has a feminist perspective which covers a wide range of from differing backgrounds, ages, roots, class, occupations, families, and sexuality in all its forms. The women cross paths in various ways and the book serves to highlight their very diverse life experiences.

Once you read it, check out our reading guide for Girl, Woman, Other.

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