I Will Always Write Back

Discuss the major racial and cultural differences between I Will Always Write Back’s main narrators, Caitlin and Martin. How have these differences shaped their friendship?

As Caitlin and Martin begin to learn about one another, they form several misunderstandings about one another. Discuss three of these misunderstandings and what they imply about their difference in background.

Caitlin’s exposure to the struggles of Martin’s family teaches her a valuable lesson about privilege. How do these lessons about privilege manifest in her life? How do these lessons depict her personal growth?

During Caitlin and Martin’s friendship, a series of global and historical events take place that affect their correspondence. Discuss three of these events in relation to the development of Caitlin and Martin’s friendship.

Caitlin and Martin’s mothers play pivotal roles in their respective children’s lives. Compare the two narrators’ relationships with their mothers. What major values has each mother imparted upon their children? How have these values impacted each narrator’s coming of age?

Throughout the book, Caitlin and Martin have access to different educational opportunities. Discuss the parallels and distinctions between Caitlin and Martin’s education journeys. How have their respective relationships to educational access informed their eventual careers as adults?

In the closing of I Will Always Write Back, Caitlin imparts the following message: “Kindness is contagious” (396). Identify three pivotal acts of kindness that have occurred in Caitlin and Martin’s narratives. How do they demonstrate the “contagious” quality of kindness?

Caitlin and Martin make each other the promise to always write to each other, no matter the circumstances. What is the significance of this promise to both narrators? How does this promise become even more meaningful when they face challenges to their regular correspondence?