55 pages • 1-hour read
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Gather initial thoughts and broad opinions about the book.
1. Timothy Keller opens by reframing the story not as the Parable of the Prodigal Son but as the “Two Lost Sons” (xvii). How did this shift in focus right from the beginning affect your reading of the parable and the book as a whole?
2. How did Keller’s exploration of spiritual homesickness, or Sehnsucht, resonate with you? In what ways does it compare to other works that tackle similar themes, like C. S. Lewis’s writings on longing (for instance, in Mere Christianity)?
3. Who is this book primarily for—religious insiders, spiritual seekers, or both? How effective do you believe Keller is at speaking to his intended audience?
Encourage readers to connect the book’s themes and characters with their personal experiences.
1. Keller presents the elder and younger brothers as archetypes for two basic life paths: moral conformity and self-discovery. In your own life or observations, where have you seen these two mindsets play out? Do you find you naturally lean toward one more than the other?
2. Consider the elder brother’s description of his obedience as joyless “slaving.” How does the book challenge you to think about your own motivations for “good” behavior?
3. The book suggests that people’s hearts can default to an “elder brother” mindset of earning favor even after embracing grace. Does this idea ring true to your experience? If you identify as a Christian, what helps you reset to what Keller calls a gospel-mode?
4. How did the book’s emphasis on grace being “costly” to the giver change your perspective on what it means to forgive in your own relationships?
5. The younger brother “comes to his senses” when he hits rock bottom (24), but the elder brother remains unaware of his own lostness. When have you seen self-righteousness become a significant barrier to self-awareness?
Examine the book’s relevance to societal issues, historical events, or cultural themes.
1. Keller suggests that early Christianity was seen as a “non-religion” or tertium quid, distinct from both religion and secularism. Why do you think modern Christianity is often perceived as just another moralistic religion, and how does Keller’s argument challenge that view?
2. How does understanding the first-century honor-shame culture change the impact of the father’s run or the elder son’s public refusal to join the feast? What might be some modern equivalents of these actions?
3. The guide connects the two brothers’ mindsets to the “culture wars” between conservative and liberal ideologies. In what ways does the book’s argument, that both are flawed self-salvation projects, offer a different lens for viewing these societal divisions?
Dive into the book’s structure, characters, themes, and symbolism.
1. Why do you think Jesus ends the parable with the elder brother still outside, leaving his decision unresolved? What is the effect of this open-ended conclusion?
2. The feast is a central metaphor, representing everything from the father’s immediate welcome to the final “marriage supper of the Lamb” (115). How does this recurring symbol illustrate salvation as being experiential, material, individual, and communal?
3. What is the significance of identifying Jesus as the “True Elder Brother” (82), a character who is absent from the parable itself? How does this interpretive move resolve the story’s central conflicts?
4. Keller analyzes the parable as a two-act drama. How does this framework, which separates the illustration of free grace in “Act One”
from its cost in “Act Two,” shape Keller’s overall theological argument?
5. Keller defines “prodigal” not as wayward but as “recklessly spendthrift” and applies it to the father’s grace. How did this influence your interpretation of the father’s character and the story’s message?
Encourage imaginative and creative connections to the book.
1. The younger brother rehearses a speech asking to be treated as a hired hand but is interrupted. If you were to write out his full speech, what would he have said? How might the story have been different if he’d delivered it before his father embraced him?
2. Imagine you get to add a final scene to the parable. What happens after the father pleads with the elder son at the door? Does he go in, and if so, what is the reunion with his brother like?
3. The book concludes with an analysis of Isak Dinesen’s story “Babette’s Feast.” If you were to create a modern story—a short film, play, or novel—that illustrates the central themes of The Prodigal God, what would your plot and characters look like?



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