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These The Woman in Me book club questions will enhance your reading experience and facilitate thought-provoking conversations about every shocking thing that the Princess of Pop Britney Spears shared in her memoir.

Plus, get a free printable PDF of the questions to take with you.

Britney Spears’s new book, The Woman in Me, is already a controversial and bestselling memoir everyone is talking about, including its shocking revelations about such topics as her teenage abortion of Justin Timberlake’s baby. More than that, though, it’s the first time the public got to hear Britney’s life story in her words. The result is something well worth reading (and discussing) in full — an account of how fame and generational trauma converged to impact one very famous young woman’s life. (Full Review of The Woman in Me)

As a decades-long Britney fan since her first hit song was released, I binge-read this memoir the day it was released in one sitting, and I drafted these The Woman in Me book club questions for you as I listened on audio, in order to give you the most comprehensive and thoughtful topics for discussion.

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The Woman in Me Book Club Questions

Discuss the significance of the title “The Woman in Me.”

Discuss the format in which you read the book, including the fact that the audio version was, for the most part, not narrated by Britney.

One of the first bold statements Britney makes is that she was raised not to disobey her parents. Discuss the significance of this statement.

Discuss music as an escape for Britney.

Britney said, “Tragedy runs in my family.” Discuss tragedy and its impacts on the various members of the Spears family, including Britney’s father.

Separate from tragedy, discuss trauma and its impacts on the various members of the Spears family.

Discuss the differences between Britney’s parents, including their upbringings.

Discuss the parenting styles of the various members of the Spears family.

Discuss the role of drugs and alcohol in the lives of the Spears family.

Britney speaks very succinctly and matter-of-factly about her rise to fame. Why?

Britney refers to herself and Justin Timberlake as “magnets.” What drew them together so fiercely?

Britney talks about the different ways in which the press spoke to her versus Justin. Discuss the role gender played in this.

Was the press fair and appropriate to teenage Britney?

Talk about the difference between perception and reality as they pertain to Britney’s fame.

Discuss the dark sides of fame in Britney’s life.

Talk about the irony in the fact that Britney was terrified of the snake used in her infamous MTV VMA performance.

Why was Britney drawn to method acting?

How may The Notebook and Chicago have been different with Britney in the lead role?

How may Britney’s life have been different if she starred in The Notebook and Chicago?

In talking about declining a role in Chicago, Britney said, “I had power back then. I wish I’d used it more thoughtfully, been more rebellious.” Why is her hindsight 20/20?

Why did Britney prefer staying in her “safe zone,” as she calls it?

Why didn’t Britney say anything before about Justin’s infidelity?

Why did Britney cheat on Justin?

Does Britney regret her abortion?

Discuss the impact of Britney’s abortion on her life both during it and thereafter.

Did it surprise you that no one knew about Britney’s abortion except Justin and Felicia?

Discuss how Britney and Justin each portrayed their breakup publicly and why.

Did the way in which Britney’s and Justin’s breakup happened surprise you?

Discuss the changes in Britney’s adolescent sister Jamie Lynn, how their relationship changed, and why.

Why did Britney begin to feel like a child again after her breakup with Justin?

About her breakup with Justin, Britney said, “There’s always been more leeway in Hollywood for men than for women[.]” Discuss this.

Discuss Britney’s experiences of shame after her breakup with Justin and how she coped with the situation.

Why was Britney happy that Justin revealed publicly their relationship was sexual?

Why were Britney’s breasts and virginity so publicly discussed? Was this appropriate?

Would a teenage girl’s breasts and virginity be fair game to discuss today?

How has Britney’s self-described empathy impacted her life?

What caused Britney’s anxiety?

What role did Britney’s time in New York City play in her life?

What role did Madonna play in Britney’s life?

Does Diane Sawyer owe Britney an apology?

Why did Britney marry her childhood friend, Jason Alexander?

What attracted Britney to Kevin Federline?

What do you make of Britney’s admissions that she was “mean” during her pregnancies?

Discuss how parenting caused Britney to become more childlike.

What mental health support did Britney lack during her pregnancies and early years of parenting?

Discuss the role of Paris Hilton in Britney’s life.

Was the press fair to Britney during her “partying” phase?

Discuss Britney’s statement, “I had no freedom, and yet, also no security.”

How did grief impact Britney’s life?

Why did Britney shave her head?

Was Britney’s attack on the paparazzi’s car justified?

Did your perception of Britney’s infamous “Gimme More” performance change after hearing her version of events?

Did your perception of Britney’s mental health crisis and psychological hold change after hearing her version of events?

Describe the role of “the photographer” and other boyfriends in Britney’s life.

What emotions drove Britney’s actions just prior to her conservatorship?

Was the conservatorship warranted?

Was the legal system fair to Britney?

Was Britney’s mother “cruel,” as Britney describes her, for publishing her memoir?

Discuss the statement of Britney’s father: “I’m Britney Spears now.”

Why did Britney go along with the conservatorship for so long?

Britney suggests her conservatorship was sexist. Do you agree?

Did anything about the conservatorship surprise you?

Discuss Britney’s statement that “people seemed to experience my body as public property” and the impact this had on her life.

Both in the book and in real life, Britney has said of her work during the conservatorship, “I wasn’t good. I was great.” What do you make of this?

How did it make you feel to learn that the conservatorship “crushed her soul” and transformed her into “a sort of child-robot” and a “bird without wings” that was “ritually tortured”?

What did Britney see in her inspiration, Reese Witherspoon?

Discuss the many parallels in the generational trauma in the Spears family, including the fact that both Britney and her grandmother were forced to take Lithium.

Why did the #FreeBritney movement mean so much to Britney?

Discuss Britney’s life post-conservatorship and what “freedom” means to her.

What got Britney through it all?

Describe Britney’s personality.

What do you think motivated Britney to write this book?

Did your perception of Britney change after reading this book?

How do you think the people referenced in the book will react to it?

What do you wish for Britney’s future?

These The Woman in Me book club questions help you foster a meaningful discussion about the complexities of fame and generational trauma, as experienced very publicly by Britney Spears. As book clubs across the world take up her memoir for discussion, it’s crucial to approach it with thoughtful questions that foster understanding and empathy. These proposed discussion questions are just the beginning of doing so.

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