Book Club: Bossypants discussion questions

Tina Fey Bossypants Review and discussion questionsBossypants by Tina Fey Discussion Questions
In case you’re in the same boat as I was and couldn’t find book club discussion questions for Bossypants anywhere, here are the book club discussion questions I came up with for our meeting. You can also check out my review of Bossypants here. If these discussion questions are helpful, please leave me a comment and let me know:

  1. How much did you know about Tina Fey before reading Bossypants? Did the book change your perception of her? Is your overall impression of Fey better or worse since reading the book?
  2. Fey is very open and honest about her self-image and quest to fit in throughout her life. She also uses a lot of self-deprecating humor when she discusses her self-image and looks. Did her struggles surprise you? If so, what parts did you find most unexpected or impacting?
  3. In the chapter titled “Growing Up and Liking It”, Fey asks the questions “When did you first know you were a women?”. In her experience with a group of women she recounted that, “almost everyone first realized they were becoming a grown woman when some dude did something nasty to them.” Does this resonate with your personal experience? If not, what was it that first make you realize you were were a woman?
  4. Fey spends a lot of time focusing on being a woman in the book; from being a working mom, to self-image, to working in a male dominated industry. What parts of Fey’s perspective on being a woman did you find most interesting? Were there parts that you could or couldn’t relate to?
  5. In the book, Fey discounts the idea that the images we see in magazines, on television, billboards, etc. are causing women to have self-image problems. On page 201 she says, “I think that we will soon see a rise in anorexia in women over seventy. Because only people over seventy are fooled by Photoshop.” Do you agree or disagree?
  6. Bossypants is written in a essay format, where each chapter focuses on a different topic or phase of her life. How did you like this style/format? Did you feel like anything was missing or left out because the books wasn’t one fluid story? Did you have a favorite section or a least favorite section?
  7. Fey addresses many issue in the book, including feminism, being a woman, how not to go on a cruise, motherhood, self-image, and leadership. If you could pick one central theme from the book what do you think it was? Do you feel like you learned anything from reading the book?
  8. Fey spends several chapters of the book discussion motherhood? Were there any parts of her perspective that surprised you? Were there any parts that you disagreed with?
  9. Satire and sarcasm hold a prominent place in the world of comedy today. What are your views on the use of these two techniques? Did your views on satire and sarcasm effect how you feel about the book?
  10. After reading the book did you feel like the title Bossypants is appropriate? Why or why not? Why do you think Fey chose that title? Did you find that the harry arms on the cover got any less disturbing after you read the book?

If you find these questions useful for your group or have questions you would add, please leave me a comment and let me know!


  1. aAnne Marie says

    This is just what I was looking for. Thank you so much for sharing. We are having book club soon, and I was feeling that Bossy Pants would not lead to a rich book discussion. After reading you questions I feel there is a lot to discuss. What other books have you been reading lately?

    • says

      I hope you’re discussion went as well as ours did. Our group is mostly moms, so we spent a lot of time talking about Fey’s insights on motherhood.

      We are currently reading In the Garden Of the Beasts by Erik Larson. It is one of the most challenging books we’ve read in the four years we’ve been meeting. But it is also very good. We just finished The Gift Giver. It was interesting but not really one of our favorites! I’m going to work on the blog this weekend while my husband is off doing his national guard thing. I’ll do a post with some more of the titles our group has read, so check back again soon!

  2. Ann says

    I am hosting book club next week and Bossypants was my choice book. Thank you for these questions-they will help iniatiate our discussion-although I expect members will have many other comments (good or bad) about her stories!

    • says

      Yes, we definitely had mixed reviews about the book. There were a few people that didn’t enjoy some of the content. But it did make for a great discussion! What other books are you all reading this year?

  3. says

    One more thank you! My book group met tonight and liked your questions a lot. It was also a book that invited straying off topic but the questions that resonated were all yours. Thank you!

  4. Saron says

    I think the questions you have a really awesome! I do have a few comments, though. As I was reading through them, I noticed that there were several grammatical errors that needed to be fixed. I also noticed that some of your questions were a little redundant, and that you could combine some of them or even omit them completely.

    Overall though, I will most definitely be using these questions for my book club!

  5. says

    I was surfing the web looking for discussion questions for BossyPants for our first book club meeting. These are fantastic!!! Thanks for sharing!!!

  6. tammy says

    I am hosting a meeting here in Chicago tonight and these questions are fantastic. Many are very similar to what I have come up with on my own…Thanks s much!

  7. Betty says

    I am hosting our book club evening on Bossypants in a couple of weeks. Thank you so much for these questions. We should have a very interesting discussion.

  8. cindy says

    Thank you for putting these on your site. They are perfect! I was looking for book club discussion questions and found yours first. I appreciate it.


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