Book Club Questions for Gentle and Lowly

1.Ortlund opens by noting that while Christians know the facts of what Jesus has done, they often feel that Jesus is perpetually disappointed or frustrated with them. Does that description resonate with you? How would you honestly describe your felt sense of how Jesus views you on an ordinary day?

2.The book's entire argument pivots on Matthew 11:29, where Jesus says, "I am gentle and lowly in heart." Why does Ortlund consider this verse so remarkable? What is surprising about Jesus making this the one self-description of his inner life found in all four Gospels?

3.Ortlund draws a distinction between what Jesus has done (his works) and who Jesus is (his heart). Why does this distinction matter? Can you think of a relationship in your own life where knowing someone's heart changed how you received their actions?

1.Ortlund argues that when Jesus says "I am gentle and lowly in heart," the word "heart" points to Jesus' most central, defining reality — not merely an emotion he sometimes feels. How does this change the way you think about Jesus' gentleness? Is it easier to believe Jesus is sometimes gentle, or that gentleness is his deepest nature?

2.The chapter examines the healing of the leper in Mark 1:40–41, where Jesus is moved with "compassion" (or in some manuscripts, "anger") and reaches out to touch the man. Ortlund says this touch was socially and religiously unnecessary — Jesus could have healed with a word. What does the unnecessary touch reveal about the heart of Christ?

3."Gentle" in Matthew 11:29 translates the Greek word praus, often rendered "meek." Ortlund explains this word conveys not weakness but a kind of strength held in restraint, condescending to the lowly. How does this definition reshape what it means that Jesus is gentle toward you specifically?

1.Ortlund opens the chapter by noting that we rarely think about whether Jesus is joyful, and that our imagination of him tends toward the grave and sorrowful. Where do you think that image comes from — is it the Scriptures, church culture, or something else?

2.Hebrews 12:2 says Jesus endured the cross "for the joy that was set before him." What was that joy? Ortlund argues it was not merely the joy of obedience completed but the joy of bringing his people home. How does that reading land on you?

3.The chapter draws on the three parables of Luke 15 — the lost sheep, the lost coin, and the prodigal son — to argue that Jesus portrays God as someone who throws a party when the lost are found. What do these parties suggest about the emotional register of heaven when a sinner returns?

1.Ortlund highlights two moments where Jesus weeps or laments — over Jerusalem in Luke 19 and his cry in Matthew 23 ("O Jerusalem, Jerusalem... how often would I have gathered your children together"). What do these moments reveal about Christ's emotional life?

2.The chapter argues that Christ's yearning is not passive wishing but an active, aching desire — a word Ortlund connects to the Hebrew and Greek terms for the deep interior of a person (the bowels, the womb). Why do you think the Bible uses such visceral, bodily language to describe God's longing?

3.Jesus weeps over Jerusalem knowing Jerusalem will reject and crucify him. What does this tell us about the relationship between Christ's love and human rejection? Does his love diminish or intensify in the face of rejection?

1.Ortlund focuses on Psalm 103:13–14: "As a father shows compassion to his children, so the Lord shows compassion to those who fear him. For he knows our frame; he remembers that we are dust." What does it mean that God's compassion is rooted in his knowledge of our weakness — not despite it, but because of it?

2.The phrase "he remembers that we are dust" could sound patronizing — as if God is simply lowering his expectations of us. But Ortlund reads it as tender, almost protective. What is the difference between those two readings? Which one feels truer to your experience of God?

3.The chapter argues that the Father and the Son share one heart — that when we see Christ's gentleness, we are seeing the Father's. How does this correct the common (but mistaken) picture of the angry Father being appeased by the gentle Son?

1.Ortlund argues that the New Testament presents Jesus with a vivid and varied emotional life — he marvels, grieves, rejoices, is angered, is troubled, and weeps. Why do you think Christians often flatten this out, preferring a Jesus who is placidly calm and emotionally neutral?

2.John 11:35 — "Jesus wept" — is the shortest verse in the Bible and one of the most theologically dense. Ortlund argues that Jesus did not weep because he was helpless (he was about to raise Lazarus) but because human death and grief genuinely moved him. What does this say about how Jesus responds to your grief and suffering today?

3.The chapter draws on Isaiah 53:3–4, noting that the Servant of the Lord is "acquainted with grief" and "carried our sorrows." The word "carried" suggests active bearing, not mere witnessing. What is the difference between a Christ who observes our pain and a Christ who carries it?

1.Isaiah 42:3 says the Servant of the Lord "will not break a bruised reed or quench a smoldering wick." Ortlund unpacks this as a picture of Christ's deliberate, careful tenderness toward the barely surviving. What bruised reed or smoldering wick in your life comes to mind as you read this verse?

2.A bruised reed is almost useless — it makes poor music and might just as well be snapped. A smoldering wick gives almost no light and fills the room with smoke. Why does Christ choose these as his images for the people he is most tenderly committed to protecting?

3.Ortlund draws on 2 Corinthians 4 to show that Paul's own experience of ministry was one of constant crushing — yet the treasure of the gospel was displayed precisely in his fragile, cracked-pot existence. How does the gospel transform weakness from something to hide into something that displays grace?

1.Hebrews 5:2 says a high priest "can deal gently with the ignorant and wayward" because he himself is "beset with weakness." Ortlund emphasizes the phrase "can deal gently" — it is a capacity, an ability shaped by experience. How does this shed light on why the incarnation was necessary, not just strategic?

2.The chapter makes much of the word "gentle" in Hebrews 5:2 (metriopathein in Greek) — a word that describes a middle path between cold detachment and excessive emotion. What does this calibrated, measured gentleness look like in practice when Christ deals with your sins and failures?

3.Ortlund draws a contrast between the Old Testament high priest (who had to offer sacrifice for his own sins as well as the people's) and Jesus, who is sinless yet fully sympathetic. How is it possible to be simultaneously sinless and genuinely sympathetic? How does Jesus' perfect obedience actually increase rather than decrease his compassion?

1.Hebrews 7:24–25 teaches that because Jesus "continues forever," his priesthood is permanent and he is able to save "to the uttermost" those who come to God through him. Ortlund lingers on the phrase "to the uttermost" — it means all the way, completely, without limit. What does it mean for your salvation that it rests on a permanent rather than temporary priesthood?

2.The chapter points out that Old Testament priests died and had to be replaced, creating an inherent instability in the system. The gospel replaces this succession of temporary priests with one permanent Priest. How does the permanence of Christ's priesthood speak to your fear that you might eventually be beyond his reach or too far gone for his care?

3."He always lives to make intercession" (Hebrews 7:25). Ortlund emphasizes the present-tense, ongoing nature of this intercession. What does it mean to you right now — in your current struggles, failures, and confusion — that Christ is actively interceding for you at this very moment?

1.Paul calls himself "the foremost" (or chief) of sinners in 1 Timothy 1:15. Ortlund points out that Paul wrote this late in life, long after his conversion — it is not a past self-description but a present one. Why does Paul not move on from this self-identification? What does it suggest about how deep Paul's grasp of grace had gone?

2.The chapter argues that Paul's awareness of his sinfulness did not diminish over time but deepened, precisely because his awareness of grace deepened. Have you experienced this in your own life — the strange paradox that growing in grace makes you more, not less, aware of your sin? How do you understand this?

3.Ortlund connects Paul's testimony to Christ's ability to save "to the uttermost" — Paul is not a worst-case scenario in which Christ barely succeeds; he is a display case for the unbounded reach of grace. How does framing the worst sinner as a trophy rather than a tragedy change the way you think about your own past?

1.1 John 2:1 says, "If anyone does sin, we have an advocate with the Father, Jesus Christ the righteous." Ortlund notes that the word translated "advocate" (parakletos) is the same word used for the Holy Spirit in John's Gospel. What does this legal-yet-personal image communicate about how Christ relates to our ongoing sin?

2.The chapter draws out a crucial tension: John writes, "I am writing these things to you so that you may not sin" — and then immediately says, "but if you do sin, we have an advocate." Why does the comfort of advocacy not lead to moral indifference? What is it about having an advocate that actually motivates holiness rather than undermining it?

3.Ortlund makes much of the phrase "Jesus Christ the righteous" — the advocate is himself the standard of righteousness he upholds. This means he does not defend us by lowering the bar but by meeting it on our behalf. How does this affect the security you feel in his advocacy?

1.Lamentations 3:22–23 declares that God's mercies are "new every morning" — written in the context of Jerusalem's destruction, which the author acknowledges was God's judgment. How does it reshape the meaning of "new every morning" to know it was written amid ruins? What does that context add to the comfort?

2.Ortlund examines Exodus 34:6–7, where God passes before Moses and declares his own name: "merciful and gracious, slow to anger, and abounding in steadfast love." This is the oldest divine self-definition in the Bible. What does it say about God's self-understanding that mercy, not wrath, is the first word he uses to describe himself?

3.The chapter presses the Hebrew word hesed — often translated "steadfast love" or "lovingkindness." Ortlund describes it as covenant loyalty infused with tender emotion — a love that will not let go. What does a love defined by covenant (not feeling alone) add to your sense of security? Why is covenant love more durable than purely emotional love?

1.Isaiah 55:8–9 famously declares that God's ways and thoughts are as high above ours as the heavens are above the earth. Ortlund applies this specifically to God's mercy — God does not extend mercy the way we do (grudgingly, with conditions, up to a point). Why is it significant that the transcendence of God is applied here to his mercy rather than his power or holiness?

2.The chapter draws on Hosea 11, where God watches Israel walk away from him and cries, "How can I give you up, O Ephraim?" In verse 9, God says, "I am God and not a man, the Holy One in your midst, and I will not come in wrath." What does God being "not a man" mean in this context? What specifically is God saying he will NOT do that a man would do?

3.Ortlund argues that when we are sinned against repeatedly, our capacity for mercy decreases — but with God, his capacity for mercy does not work that way. The very holiness that makes sin so serious also makes God's mercy so inexhaustible. How do holiness and mercy reinforce each other in God's character?

1.Ephesians 2:1–3 describes our pre-conversion state in the darkest terms: dead in sins, following the devil, living in the flesh, children of wrath. Ortlund does not soften this portrait. Why is it important to feel the full weight of this description before moving to verse 4? What is lost if we rush past "dead" to get to "But God"?

2.Ephesians 2:4 opens with "But God, being rich in mercy, because of the great love with which he loved us." Ortlund notes that Paul links God's mercy to God's wealth — he is not merely merciful, he is rich in mercy. What is the difference between a merciful God and a God who is rich in mercy? What does wealth imply?

3.Romans 5:20 says that "where sin increased, grace abounded all the more." Ortlund presents this as a kind of divine counterintuitive arithmetic: the worse it gets, the more grace is unleashed. What risks come with this statement (which Paul addresses in Romans 6), and why does he still make it so boldly?

1.Ortlund uses the Song of Solomon — traditionally read by many in the church as an allegory of Christ's love for his people — to speak of Christ's passionate pursuit of the believer. Does reading the Song of Solomon this way feel natural or forced to you? What are the limits and the benefits of this interpretive approach?

2.Jeremiah 31:3 records God saying, "I have loved you with an everlasting love; therefore I have continued my faithfulness to you." Ortlund emphasizes the word "therefore" — the faithfulness is the result of the love, not its cause. What does it mean that God's continuing acts of faithfulness toward you are driven by love rather than obligation?

3.The chapter explores the idea of being "drawn in" — not merely invited but pulled by love into relationship with God. What is the difference between a God who issues an open invitation and a God who actively draws? How does this connect to the doctrines of election and irresistible grace?

1.Zephaniah 3:17 says God "will rejoice over you with gladness; he will quiet you by his love; he will exult over you with loud singing." This is one of the most startling verses in the Old Testament. What is your initial, honest reaction to the image of God singing over you with joy?

2.Ortlund notes that the God of the Old Testament is sometimes portrayed as emotionally distant or predominantly wrathful in popular Christian imagination. How does Zephaniah 3:17, Isaiah 62, and the trajectory of Old Testament passages in this chapter challenge that caricature?

3.Isaiah 62:5 says God rejoices over his people "as the bridegroom rejoices over the bride." This is the Father using romantic joy as the closest available metaphor for his feeling toward his people. What does this metaphor add to your understanding of the Father's heart that more formal or legal language cannot convey?

1.Romans 8:31 asks, "If God is for us, who can be against us?" Ortlund treats this not as a rhetorical question that shuts down all opposition but as a question that acknowledges real opposition — and then answers it with the greater reality of God's "for-ness." What does it mean for God to be "for" you? How is this different from God simply being kind or tolerant?

2.Paul lists a series of things that cannot separate us from the love of Christ: hardship, distress, persecution, famine, nakedness, danger, sword. These are all external sufferings. He then adds: height, depth, things present, things to come, powers, death, life, angels, rulers. What do these escalating lists suggest about the comprehensiveness of Christ's protective love?

3.Ortlund argues that the most threatening item on Paul's list, for most modern believers, is not persecution or danger but the fear that our own sin and failure will finally separate us from Christ's love. Where does Paul address this fear specifically in Romans 8? How does his argument hold?

1.Psalm 23:4 shifts from "he" to "you" — "Even though I walk through the valley of the shadow of death, I will fear no evil, for you are with me." Ortlund notes this grammatical shift as significant — in the darkest valley, the psalmist stops talking about God and starts talking to him. Why does personal address become necessary in the place of deepest darkness?

2.Isaiah 43:2 says, "When you pass through the waters, I will be with you; and through the rivers, they shall not overwhelm you; when you walk through fire you shall not be burned." Note that God does not promise the waters will be avoided but that they will not overwhelm. How does this distinction between deliverance from and presence through suffering change the way you pray in dark seasons?

3.Ortlund argues that Christ's suffering in Gethsemane and on the cross was the deepest darkness anyone has ever walked through — and that he walked through it so that no believer ever walks through darkness alone. How does the cross function not just as payment for sin but as companionship in suffering?

1.Matthew 28:18 records Jesus saying, "All authority in heaven and on earth has been given to me." Ortlund argues that this authority belongs to the same Jesus described in Matthew 11:29 as gentle and lowly. Why is it important that these two descriptions of Christ go together — that power and gentleness belong to the same person?

2.The chapter argues that Christ's authority is not exercised despite his gentleness but through it — the authority of the cross is an authority exercised by surrendering power in love. How does the cross redefine what authority looks like? How does it challenge worldly models of power?

3.Philippians 2:9–11 says that precisely because Jesus humbled himself to the point of death, God exalted him above every name. The path to all authority ran through lowliness. What does this pattern — humility leading to exaltation — mean for the Christian life? What does it mean for how we exercise whatever authority we have?

1.Philippians 1:6 says, "He who began a good work in you will bring it to completion at the day of Jesus Christ." Ortlund anchors the believer's perseverance not in their ability to hold on but in Christ's determination to complete what he started. How does this reframe the question of "Will I make it?" into a different question entirely?

2.John 10:28–29 records Jesus saying that no one can snatch his sheep out of his hand — or out of the Father's hand. The double protection (Son's hand and Father's hand) is striking. What does this layered security say about how seriously God takes the keeping of his people?

3.Ortlund addresses the tension between the doctrine of perseverance and the many biblical warnings against falling away (e.g., Hebrews 6). How does he hold these together? Is the doctrine of perseverance a guarantee of complacency, or is it the only basis for genuine fighting against sin?

1.Ephesians 3:18–19 prays that believers would "comprehend... the breadth and length and height and depth" of the love of Christ and "know the love of Christ that surpasses knowledge." Ortlund lingers on the paradox: you are being asked to know what you cannot fully know. What does it mean to grow in knowing a love that exceeds the capacity of knowledge?

2.The chapter uses the phrase "exploding heart" to describe Christ's love — a love so large it cannot be contained in any single chapter, any single metaphor, or any single lifetime of experience. How have the twenty chapters that preceded this one begun to enlarge your sense of the size of Christ's heart for you?

3.John 17:24 records Jesus praying to the Father: "Father, I desire that they also, whom you have given me, may be with me where I am, to see my glory." Christ's deepest desire for his people is not merely their forgiveness but their presence with him in glory. What does it mean that Christ wants you with him? How does this move beyond the transactional into the relational?

1.Looking back at the full book, which single chapter or theme was most impactful for you? What made it hit so hard? Was it a truth you had never heard, or a truth you had heard but never quite believed until now?

2.Ortlund's central verse is Matthew 11:29 — Jesus describing himself as "gentle and lowly in heart." How has your understanding of this verse changed from Week 1 to now? What do those two words mean to you now that they did not mean before?

3.The book draws heavily on the Puritan writers — Thomas Goodwin, Richard Sibbes, John Bunyan, John Owen. Did engaging their voices surprise you? Did any particular Puritan quote or image stay with you? What does it suggest about the faith that such old words still feel so alive?