THE CROSSING GUARDS 

Discussion Questions

1. The Meaning of the Title

The phrase 'Crossing Guard' carries literal, medical, emotional, and philosophical weight throughout the novel.​

• Did your understanding of the title change by the end of the book?

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2. Megan Wallace and the Cost of Compassion

Megan dedicates her life to caring for people at the end of theirs.

• What do you think drives her to hospice work?

• Where do you see compassion turning into self-sacrifice?

• Do you think Megan is avoiding something in her own life by focusing so intensely on others?

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3. Jackie Boy Hayes: Strength or Stubbornness?

Jackie Boy defines himself as a Marine first—and last.

• How does his military identity both help and hurt his relationships?

• Is his tire-dragging ritual an act of discipline, grief, defiance, or all three?

• In what ways is Jackie Boy preparing for death, even as he refuses to acknowledge it?

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4. Father and Daughter

The relationship between Megan and Jackie Boy sits at the emotional core of the novel.

• How do they express love differently?

• What do they understand about each other without ever saying out loud?

• How does their bond evolve over the course of the story?

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5. Dying Alone vs. Being Alone

Megan insists that no one should die alone, while other characters accept solitude as inevitable.

• Is there a difference between dying alone and feeling alone?

• Which characters experience loneliness even while surrounded by people?

• Do you agree with Megan’s belief—or do you think some people choose solitude at the end?

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6. Humor in the Face of Death

Despite its subject matter, the novel is often funny—sometimes uncomfortably so.

• How does humor function as a survival tool for these characters?

• Were there moments where laughter surprised you?

• Did humor ever make the emotional moments hit harder?

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7. Community as Character

Boston—especially South Boston and East Boston—is more than a setting.

• How does place shape the characters’ identities and values?

• In what ways does gentrification function as a quiet antagonist?

• Could this story exist anywhere else?

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8. Secondary Characters and Moral Mirrors

Characters like the Giordano family, Tim Wallace, Loretta, Davey, and Tricia reflect different approaches to love, duty, and denial.

• Which supporting character stayed with you the most, and why?

• Who represents the kind of life Megan might fear—or secretly want?

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9. Control vs. Acceptance

Many characters struggle with control: over bodies, routines, memories, and outcomes.

• Where do you see characters fighting against what cannot be changed?

• Where do you see moments of surrender—and are they peaceful or painful?

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10. The Ending (Spoilers Encouraged)

Without giving specifics, the ending asks readers to sit with unresolved emotions rather than neat closure.

• Did the ending feel hopeful, devastating, or honest?

• What does the novel ultimately suggest about how we should live, knowing life is finite?

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Reflection Prompts 

• Which character reminded you most of someone in your own life?

• Has this book changed the way you think about aging, caregiving, or death?

• What would “showing up” look like in your own life right now?

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Suggested Pairings & Activities

• Pair discussion with a conversation about hospice care, end-of-life planning, or family caregiving.

• Invite a healthcare worker, veteran, or caregiver to share perspectives.

• Consider reading the opening Castle Island chapter aloud—it’s a powerful entry point.