Once Upon a List | The Perfectly True Tales of a Perfect Size 12

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Once Upon a List


  1. Which items on Clara’s list were most challenging to her? Which would you have the hardest time completing? Did any appeal especially to you?

  2. Have you ever written a “bucket list”? If so, what sort of items were on it, and have you completed any of them? If you haven’t, why not?

  3. Clara’s time capsule list was created at age ten, “before reality encroached upon that magical sense of childhood power that allowed her to believe anything was possible.” Considering the person who you were at age ten, how does that child compare and contrast to who you are today? Did your childhood hopes, dreams and desires impact who you are now? If you got lost somewhere along the way, what can you actively do to “find” yourself again?

  4. At the beginning of Once Upon A List, it is established that Sebastian is the love of Clara’s life - she refers to him as her “soul mate.” And then she reunites with Lincoln and falls in love all over again. Do you think it is possible to have more than one soul mate? Is it really possible to find true love more than once? Can you be in love with more than one person?

  5. What characteristics attracted Clara to Lincoln? Do you think she would have been drawn to him if Sebastian hadn’t passed away?

  6. Once Upon A List begins with the quote, “Grief turns out to be a place none of us know until we reach it.” Later in the book, Lincoln echoes this sentiment, remarking to Clara, “We’re both aware that nothing, I mean nothing, prepares you for handling death. Unfortunately, you don’t just wake up one day and say, Okay, I’m done with mourning, and now it’s time to go right back to the normal life I had.” Was Clara’s reaction to Sebastian’s death realistic? What aspects of Clara’s grief can you relate to? What does Clara’s experience tell us about grief? How have you reacted to death?

  7. What dream of yours do you fear might never happen if you died suddenly?

  8. Do you think someone ever moves on from a loss such as one that Clara experienced?

  9. Love, death, redemption, and self-discovery are central themes in this book. Which theme made the most impact on you - and why?

  10. All of the supporting characters who Clara encounters while fulfilling items on her list (i.e. Billy/William Warrington, Frank the proprietor of Frank’s Antiques, and the teenage Plunge Boy from Noah’s Ark) play a key role in helping her to learn an important lesson and advance with her life. Which supporting character did you like best? Which one would you most want for a friend - and why?

  11. The notion of loyalty and commitment comes up throughout the book: Clara’s loyalty toward Sebastian and her guilt about starting a new relationship with Lincoln, Clara’s commitment to mending her fractured friendship with Tabitha, even Leo, with his unwavering support of Clara. When is it okay to acknowledge that something ? a relationship, a person ? has died and that the person left behind can start anew?

  12. The concept of family manifests itself continually throughout the novel. Describe the role family plays in Clara’s life. Who is the central figure in Clara’s life?

  13. According to the popular saying, “You can never go home again.” Yet, for Clara, it seems the only place for her to go was home. What function does home play in her path toward recovery? Could she have healed and found joy if she stayed in Boston?

  14. By the end of the book, Clara feels that she’s changed. What do you think had the biggest impact on her transformation?

  15. If you had to distill the themes and essential storyline of Once Upon A List into three sentences for a write-up in the "And Bear in Mind" section of The New York Times Book Review, what would you say?

  16. What do you think happens after the last page of the novel? Where do you see Clara, Lincoln, Leo, Libby, and Tabitha five years after the close of the book? Outline the story arc of a Once Upon A List sequel.

The Perfectly True Tale of a Perfect Size 12


  1. Describe Delilah White both physically and psychologically.  What is her character’s greatest strength?  What is her character’s greatest weakness?

  2. Compare and contrast the portrayal of body image and self-esteem in this novel with another contemporary book featuring a female protagonist (i.e. Bridget Jones’s Diary).  What similarities or differences do you notice in the depiction of the characters?  How does each character deal with their individual self-esteem and confidence issues?  Describe Delilah’s view of herself and how it relates to that of today’s “average” modern woman.

  3. Cherry Pond is a central setting in the novel.  How is it a metaphor for the relationship between Delilah and Jack?  How is it a metaphor for the relationship between Sofia and Delilah?  How is it a metaphor for life?  If you were invited to spend a weekend at Cherry Pond and could bring along one guest, who would it be and why?

  4. Towards the end of the novel, Delilah shares an important discovery with Sofia, explaining, “The Margo Harts of this world, sadly enough, are a dime a dozen.  Our industry’s crawling with them!  Hell, the world’s crawling with ‘em!” Are you more or less sympathetic to Margo’s character by the end of the book?  Why?  What is her character’s greatest strength?  What drives and motivates Margo?  How does this compare or contrast to what drives and motivates Delilah?  Have you ever encountered a “Margo Hart”?  If so, how did this person make you feel?  

  5. There’s a large cast of supporting characters in “The Perfectly True Tales of a Perfect Size 12.”  Were there any that you wish were featured more prominently in the novel?  If so, who and why?  Which character in the book do you most identify with?  Why?  Which character do you consider to be the least relatable?

  6. The novel concludes with the words, “The Beginning.”  What did you think of this ending?  Would you like to see “The Perfectly True Tales of a Perfect Size 12” turned into a book series?  If Delilah’s perfectly true adventure does indeed continue, describe some of the things you’d like to see happen in the next book.  What are some of the things that you would not like to see happen?  What role do you envision Margo Hart playing in the next installment?  

  7. How would Delilah’s character and the overall story change if she was not a perfect size 12, but rather a smaller or larger size?

  8. “The Perfectly True Tales of a Perfect Size 12” explores several main themes including self-actualization and its correlation to personal happiness and fulfillment.  What is your own definition of “happiness”?  Are you happy?  For Delilah to create her own happiness, she acknowledges that she must take a large, frightening risk.  She does not accept this fact until she reaches a particularly low point (…maybe, she just had to sink to a certain level of desperation, the kind of desperation that makes one quake first with fear, and then with enlightenment, to find the courage required to face the truth and take the leap into the unknown, having the faith in herself to know she can succeed, if only she’ll let herself try.).  Do you believe Delilah would have quit her job at Domestic Bliss in order to pursue her real dream if Margo had not come to Cherry Pond or sabotaged her at work in the first place? 

  9. Discuss some of the ways in which the concept of independence plays a significant role in the book.

  10. What is your favorite scene in the book?  Why? 

  11. If the novel were a movie or TV show, whom would you cast as Delilah, Jack, Margo and Sofia?

  12. Is “The Perfectly True Tales of a Perfect Size 12” a fairy tale?  If so, why?

  13. “The Perfectly True Tales of a Perfect Size 12” is about:
    A.) Personal achievement
    B.) Professional achievement
    C.) Body size
    D.) Dueling domestic divas
    E.) A, B, & D

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