1. Based on the first chapter, describe Jenna by highlighting her physical appearance, emotional state, and character traits.

2. Jenna has a distressing interaction with her intoxicated father, which she recounts to her mother and sister, Faith. How would you suggest Jenna approach the situation with Faith? Is there a method to protect siblings while still being honest about a difficult experience?

3. Jenna's closest companion is her Grandma Boiler, who resides in a nursing home due to Alzheimer's disease and requires specialized care. During her visits, Jenna uses a memory board with her grandmother. What is a memory board, and what purpose does it serve?

4. Jenna is astonished that Mrs. Gladstone would choose her, a newly licensed driver, to be her personal chauffeur. Jenna aspires to be a competent driver. List the qualities that define a good driver. Which of these qualities does Jenna possess?

5. How would you feel if you were tasked with Jenna's job of driving Mrs. Gladstone in her Cadillac from Chicago, Illinois, to Dallas, Texas? Given that Jenna has only been licensed for six months, how do your feelings compare to Jenna's?

6. Jenna's trip preparations resemble those an adult or parent would make for a six-week absence. Why is Jenna taking on these responsibilities instead of her mother?

7. Jenna conducts some investigative work in the Peoria, Illinois store and other locations along the route. How does her detective work benefit Mrs. Gladstone?

8. How does Harry Bender's advice assist Jenna during her initial meeting with Elden Gladstone? Does she manage the situation effectively? What are some techniques for handling angry individuals?

9. Alice Lovett and Mrs. Gladstone seem like unexpected friends. Compare and contrast their personalities. Why do they maintain a friendship?

10. When Elden visits Mrs. Gladstone's home in Dallas, why does she keep Jenna with her during their conversation? Why does she introduce Jenna as her assistant to Elden?

11. Jenna realizes her father needs help with his alcohol addiction but is unsure how to provide it. From where does Harry Bender's assistance originate? Can Jenna offer similar support to her father?

12. Past experiences can sometimes influence our present actions. This is true for Jenna. Explain why she finds it easier to write letters than to speak on the phone.

13. Jenna diligently does her homework and visits the library to learn about Ken Woldman. What did her grandmother mean by saying, "God made libraries so that people didn't have any excuse to be stupid"? Why was Jenna interested in Ken Woldman, and how will this information benefit her?

14. In the novel, Jenna reflects on Mrs. Gladstone's teachings about hope, Harry Bender, work, and grace. What do these lessons signify for Jenna?

15. Discuss the irony surrounding Harry's death.

16. Upon returning to Chicago, Jenna faces the challenging task of confronting her father. Despite a plethora of painful memories associated with him, there are also positive ones that sustain her. What are these memories? What actions does Jenna take to free herself from the weight of her father's influence? What outcomes arise from her efforts? What insights does she gain about herself in the process?

17. By the conclusion of the story, the relationship between Jenna and Madeline Gladstone evolves beyond a typical employee-employer dynamic. What nature does this new relationship take, and how does it develop over time?

18. At the novel's conclusion, Jenna experiences a transformation in her self-confidence and self-perception. What drives these changes, and are they permanent?

19. Using examples, how does humor play a role in enhancing the story's overall impact?