Book Club Questions for Prayer: Experiencing Awe and Intimacy with God

1.Keller observes that many Christians feel a persistent guilt about their prayer lives—they know they should pray more and better, but the guilt itself seems to make things worse. Do you identify with that pattern? What does your typical experience of prayer actually feel like right now?

2.The subtitle of the book promises 'awe and intimacy with God.' Keller argues these two qualities—awe (a sense of God's transcendence and holiness) and intimacy (a sense of God's nearness and fatherly love)—must be held together in prayer. In your experience, do you tend toward one more than the other? What happens to prayer when awe eclipses intimacy, or when intimacy eclipses awe?

3.Keller frames this book partly as a sequel to Counterfeit Gods, arguing that prayer is the primary means of dismantling the idols of the heart. Why might prayer—rather than, say, willpower or accountability—be the right tool for that job? What does that say about what prayer actually is?

1.Keller argues that all the great figures of Scripture—Moses, David, Paul, and above all Jesus himself—were people of extraordinary prayer. What does Jesus's own prayer life (the fact that the sinless Son of God prayed constantly) tell us about what prayer is for?

2.Keller draws a distinction between prayer as a 'spiritual discipline' (something you add to an otherwise functioning life) and prayer as the very means by which the Christian life operates. How does that distinction land for you? Does your current schedule reflect the second understanding or the first?

3.Keller notes that Jesus in Luke 18 tells his disciples a parable specifically 'to the effect that they ought always to pray and not lose heart.' What does it say about the nature of prayer that the main enemy Keller identifies in this chapter is not laziness or busyness but discouragement?

1.Keller offers a working definition of prayer as 'continuing a conversation that God has already started through his Word and his grace.' How does framing prayer as a response rather than an initiation change how you approach it?

2.Keller distinguishes between 'the prayer of the mind' (saying correct things to God) and 'the prayer of the heart' (actually communing with God in a way that moves and changes us). Do you recognize that distinction in your own experience? What causes prayer to stay in the mind rather than reaching the heart?

3.Keller engages with the writings of Augustine, particularly Augustine's famous restlessness ('our heart is restless, until it repose in Thee'). How does Augustine's understanding of the soul's longing for God illuminate what prayer is at its deepest level?

1.Keller emphasizes that Christians have access to God not as petitioners approaching a distant king but as children approaching a Father—and specifically, as people who approach God through the intercession of Jesus, who is himself praying for us (Hebrews 7:25). How often do you actually think about Christ's ongoing intercession when you pray? How might it change your posture?

2.Keller draws on the imagery of Hebrews 4:16—the 'throne of grace'—to hold together God's majesty and God's mercy. A throne is an image of power and authority; grace is entirely undeserved. What happens to prayer when we approach only the throne (keeping God at arm's length) or only the grace (losing all reverence)?

3.Romans 8:26–27 tells us the Spirit intercedes for us 'with groanings too deep for words.' How does the doctrine of the Spirit's intercession address the experience of not knowing what to pray—or of feeling too broken or confused to form words?

1.Keller draws heavily on Martin Luther's practice of 'praying the catechism'—taking doctrinal content and turning it into personal address to God. Have you ever tried to turn a passage of Scripture or a theological statement directly into prayer? What happened? What made it easy or hard?

2.Keller argues that reading the Bible without prayer leads to mere information, while praying without the Bible leads to subjectivism—we end up inventing a God to suit ourselves. How does this help explain why both 'Bible people' who rarely pray and 'prayer people' who rarely study the Word can end up spiritually stunted?

3.Keller describes 'meditative prayer'—not emptying the mind but filling it with Scripture and allowing that content to descend from the head to the heart. What is the difference between reading the Bible as study and reading it as the opening move in a conversation with God?

1.Keller argues that self-knowledge and knowledge of God are deeply intertwined—that honest prayer is one of the primary means by which we come to know ourselves truly. Do you experience prayer as self-revealing? When have you discovered something about yourself through praying (or through avoiding prayer)?

2.Keller revisits the idea of 'idols of the heart'—the things we trust for significance, security, and satisfaction more than God. He argues that our prayer lives often reveal our idols: we pray anxiously about what we treasure most and barely at all about everything else. What do your prayers (or your prayer anxieties) reveal about what you actually treasure?

3.Keller describes 'reflective prayer'—praying in a way that turns the searchlight of the gospel on our interior life, examining our fears, desires, and responses in light of who God is. How is this different from mere introspection or psychological self-analysis? What makes it genuinely prayer rather than just journaling?

1.Keller uses the story of Jacob wrestling with God at Peniel (Gen. 32) as an extended image for prayer. Jacob refuses to let go until he receives a blessing. What does this image say about the disposition prayer requires—specifically about perseverance, honesty, and the willingness to be hurt in the process?

2.Keller also points to the description of Moses speaking with God 'face to face, as a man speaks with his friend' (Exod. 33:11). What kind of friendship is implied in that description? How does it compare with how you currently experience your conversations with God?

3.Keller distinguishes between prayer as monologue (talking at God) and prayer as genuine dialogue (a conversation in which we also listen). What does it mean to listen in prayer? What makes it difficult, and how is listening in prayer different from simply waiting for an emotional experience?

1.Keller draws heavily on Psalm 51—David's great prayer of confession after his sin with Bathsheba—as a model for how deep, honest confession works. What makes David's confession in that Psalm different from a mere apology or a legal petition? What is David actually asking God to do?

2.Keller distinguishes between 'legal confession' (confessing sin to restore standing before God) and 'relational confession' (confessing sin because it has damaged closeness with God as Father). For a Christian who is already justified, why does confession still matter? What does it restore?

3.Keller warns against two failure modes in confession: the person who confesses glibly without real conviction, and the person who confesses with such excessive guilt that they can never accept forgiveness. Do you recognize either pattern in yourself? What produces each one, and what is the gospel's answer to both?

1.Keller argues that adoration is the 'highest form of prayer' because it is the only form that is entirely about God rather than about us or our needs. Does that claim surprise you? How much of your typical prayer time is petitional versus purely worshipful? What does the balance reveal?

2.Keller notes that adoration is not simply 'saying nice things to God' but involves genuinely beholding God—fixing the mind and heart on specific attributes and works of God until something like wonder or joy rises in us. What makes the difference between going through the motions of praise and actually experiencing what Keller is describing?

3.Keller draws on C.S. Lewis's observation that in praising something we genuinely love (a sunset, a poem, a friend), we are completing or expressing the joy rather than adding to the thing being praised. How does Lewis's insight change the way you understand why God commands us to praise him? What does this say about what praise does to us?

1.Keller argues that petition is legitimate and important—that God genuinely invites us to bring our needs to him—but that it becomes distorted when it is all we do in prayer. What shape does your petitionary prayer usually take? Is it more like a shopping list or more like a child talking to a parent?

2.Keller unpacks the structure of the Lord's Prayer (Matthew 6:9–13) as a model for all prayer, noting that it moves from God's concerns ('Your kingdom come, your will be done') before our concerns ('Give us this day our daily bread'). What does that ordering teach us about the posture from which petition should arise?

3.Keller addresses the question of unanswered prayer directly and honestly—one of the most pastorally sensitive topics in the book. He argues that prayer changes us more reliably than it changes circumstances, and that this is itself a form of God's goodness. How does that claim strike you? Does it feel like a consolation prize, or does it carry genuine weight?

1.Keller notes that both Daniel and Jesus had fixed, daily times of prayer—not because they were rigid but because they understood that consistent access to God requires consistent habits. What is the relationship between habit and authenticity in prayer? Can a scheduled prayer time be genuine, or does scheduling it make it merely mechanical?

2.Keller outlines a basic pattern for daily prayer that moves through adoration, confession, thanksgiving, and supplication (sometimes called ACTS). He argues this structure is not a cage but a scaffold—it helps us not to forget whole dimensions of prayer. Have you ever used a structured approach to prayer? What did you find helpful or unhelpful about it?

3.Keller recommends spending significant time in the Psalms as a daily practice, using them both for content (learning what to say to God) and for emotional honesty (finding words for what you actually feel). Is there a specific Psalm you have returned to repeatedly? What is it, and what keeps drawing you back?

1.Looking back across the whole book, which single chapter or idea landed most powerfully for you—and why? Was it a new idea, or was it something you already believed but hadn't yet felt?

2.Keller's central thesis is that prayer is the primary means by which the gospel moves from the head to the heart and produces genuine, lasting character change. Has that thesis been confirmed, challenged, or complicated by your experience over these weeks? How has your understanding of what prayer is changed?

3.Think back to Week 1, when you described what your prayer life actually felt like at the start of this study. How would you describe it now? Be honest—not just about positive changes but about where the struggle remains.