Someone to Watch Over explores a range of contemporary family and societal issues. Presented here are topics and questions for discussion included in the book.

William would be delighted to visit virtually with book clubs and library gatherings via such platforms as Zoom and Skype to participate in a conversation about the book. If you’re interested in arranging such a visit, please email him at

Downloadable PDF available here.

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Questions & Topics for Discussion

  1. A primary theme in the book is family dynamics and how a person’s life trajectory often defines his or her family relationships. When we meet Lennie and John, we realize their lives went in very different directions. Why do you think they were able to reach a better understanding and appreciation of each other?
  2. Lennie’s journey took her to different places and into many unique experiences. What do you think her life would have been like if she had stayed in Mosely after having her child?
  3. Lennie’s resolve to reconnect with her father is abruptly interrupted by his death, combining grief with regret. She finds forgiveness, in part, because she believes he is helping her to find Michelle. Do you believe Lennie was helped by her deceased parents and Joella, or were those experiences due to her emotional state and desire to find answers? How does belief in the afterlife help people?
  4. Lennie describes her encounter with Boone as the first time a boy paid her that type of attention, and she liked it. Given how the encounter played out, how do you think this impacted Lennie’s ability to maintain future relationships with men?
  5. What part of the story was your favorite and why?
  6. Mosley is a fictitious small town in Tennessee with clear power dynamics between those with resources and those reliant on those who possess the resources. What is your experience with this type of situation? What was your reaction to the encounter between Mr. Mosely and Lennie at the cemetery when returns to the small town after finding Michelle?
  7. John is convinced he will better understand his deceased father by re-creating a family vacation taken many years earlier. Why do you think he was so adamant about aspects of the trip such as the car, the route, and the same stops? Did you find his reaction to events that undermined his goal understandable or unreasonable?
  8. As the story unfolds, we learn about events pertaining to Michelle’s adoption that were unknown to Lennie and her father. Have you ever unearthed a “family secret” or information that changed your understanding of past events? How did this make you feel?
  9. Knowing a person’s backstory can oftentimes change our perception of him or her. Describe a time when you learned more about someone else’s experiences and how that changed your feelings about him or her.
  10. Lennie’s car plays an important role in this story. What of your current or past possessions hold a special place in your life? What made that connection so important?
  11. Both Lennie and Michelle wrote letters to their absent mothers. How can writing letters, journaling, or creative expression such as poetry or music help people deal with life’s unknowns? Do you write or play music or have another type of creative outlet, and if so, how does it help you?
  12. Reconciliation is a complicated process. What was your reaction to Michelle’s anger the first time she meets Lennie? What do you think their relationship was like after the story ends?