“Well, That Was Awkward” by Rachel Vail: A Discussion Guide For Writers

discussion questions prepared by Kelly Carey


Rachel Vail puts a modern middle-grade twist on the classic tale of Cyrano de Bergerac in Well, That Was Awkward. Using text messages, Vail’s protagonist helps her best friend respond to a new love. Vail adds tension by giving her protagonist budding feelings for her friend’s new love interest, including a classic nasty mean girl antagonist, and providing parent drama. By studying Vail’s novel, writers can explore the opportunities presented by updating classic tales, the use of text messaging in middle grade novels, the effect of setting on story, and the balance of plot and subplot.

Use the discussion questions on your own or with a book group to investigate Well, That Was Awkward. As you consider each question, take note of how your own manuscripts apply Vail’s methods.



These discussion questions were inspired by the KidLit Book Club meeting at The Writers’ Loft. We’d love to have you join us. Check out the Loft calendar to find out about our next meeting!

Discussion Questions:

  1. Consider how Vail manipulated the original tale of Cyrano de Bergerac to make it modern and age appropriate. For example, Vail traded poetic love letters for witty text messages. What did she do that was successful? Could she have stayed closer to the 1897 play and still appealed to today’s middle-grade readers?
  2. Vail chose to make her “Cyrano” a girl. How did this influence the story? How did it affect the romantic entanglements? When presenting a fractured fairy tale or drawing from a classic piece of literature, what twists can authors invent to remake the story as their own?
  3. Children’s fiction often presents a close friendship between a girl and a boy. How realistic is this? How does this fictional friendship between Gracie and Emmett aid the story and/or make it more appealing? Did Gracie need to be best friends with Emmett? What friendships have you given the MC in your own novels? Are those friendships realistic, and how do they help you tell your story?
  4. How does the city setting benefit Vail’s plot and character development? What would have happened if the novel were set in a small town? Rural farm country? How did the easy walkable proximity of young characters, who don’t have driver’s licenses, help Vail in structuring her story scenes? How have you been helped or hurt by your setting when trying to put young characters in the same place, without their parents, and without resorting only to the time they spend in school?
  5. Was Riley a great villain? How did Riley’s character and actions move Gracie’s story forward? How would the story have changed if Riley were not as mean? Consider the villain or antagonist in your own manuscripts. What have you done to make them truly nasty? Have you allowed them to be more than just a villain?
  6. How did the plotline of Gracie’s dead sister help the story? Could the story have been presented without this plotline? How would it have changed? Did this storyline give the novel tension? And did it help give insight into Gracie? How do you balance plots and subplots in your own manuscripts?
  7. Could the cause of Gracie’s sister’s death have been less accidental and more intentional? How would that have affected the story? Would it have changed the potential reader?
  8. Did the parent/sister storyline match the tension of the AJ/Emmett romance plotline? How did the two plots work together to improve the story? Were there times they worked against each other and the story?
  9. How has Vail captured the tension, importance, and drama of teen lives? An adult may look at some of Gracie’s worries and feel they are insignificant or even silly. How do adult authors stay in touch with teen problems?
  10. Vail presents a modern middle-grade tale devoid of swearing, violence, and sex (with the exception of kissing). How will this help the marketing of her novel? How do you manage language, violence, and sex in your novels?

To learn more about Rachel Vail, visit her website at http://www.rachelvail.com/about-rachel/.

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