22-Week Study & Discussion Guide

Gentle and Lowly

by Dane Ortlund·155 discussion questions

Week 1 — FreeRead the Introduction of Gentle and Lowly. Primary Scripture: Matthew 11:28–30

Discussion question your group will work through:

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?

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About This Study Guide

At a glance: this is a 22-week study and discussion guide for Gentle and Lowly by Dane Ortlund, with 155 questions organized by reading assignment. Week 1 is free to read, with no card required.

Gentle and Lowly: The Heart of Christ for Sinners and Sufferers by Dane C. Ortlund is a book with one simple, stunning thesis: the deepest impulse of Jesus Christ's heart is not frustration, disappointment, or reluctant tolerance — it is tender, zealous, and inexhaustible love for sinners. Drawing on Matthew 11:29, where Jesus describes himself as "gentle and lowly in heart," Ortlund mines the Old and New Testaments and draws heavily on the Puritan writers — Thomas Goodwin, Richard Sibbes, John Bunyan, John Owen, and others — to show that the gospel does not merely change what God does for us; it reveals who God is toward us. The book is not primarily about what we must do but about what kind of Savior we actually have.

To use this guide well, read the assigned chapter before your group meets (or before your personal study time). Sit with the questions for a few minutes before writing or discussing — many of them ask you to go somewhere honest and personal, and that takes a little courage. Journaling your answers before the group conversation will help you go deeper. If you are studying alone, treat the closing prayer not as a formality but as the destination: the goal of every chapter is not just new information but a warmer, more trusting relationship with the Jesus the chapter describes.

Over the course of this guide you will likely find that your working mental image of Christ is corrected, enlarged, and ultimately transformed. Readers consistently report that Gentle and Lowly does not feel like a theology book — it feels like good news heard for the first time. The aim of this study is that you would finish it not merely knowing more about Christ's heart but actually resting in it, bringing your failures and your suffering to a Savior you are no longer afraid of.

Introduction — His Very Heart

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Open Week 1

Read the Introduction of Gentle and Lowly. Primary Scripture: Matthew 11:28–30

Before diving into the chapters, Ortlund lays out the one question the whole book exists to answer: what is Jesus Christ actually like in his heart toward us? Sit with that question this week.

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?

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Chapter 1 — His Very Heart

All 7 questions

Read Chapter 1 of Gentle and Lowly. Primary Scripture: Matthew 11:28–30; Mark 1:40–41

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?

+ 6 more questions in the full guide

Chapter 2 — The Happiness of Christ

All 7 questions

Read Chapter 2 of Gentle and Lowly. Primary Scripture: Hebrews 12:2; Luke 15:1–32

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?

+ 6 more questions in the full guide

Chapter 3 — Yearning

All 7 questions

Read Chapter 3 of Gentle and Lowly. Primary Scripture: Luke 19:41–44; Matthew 23:37

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?

+ 6 more questions in the full guide

Chapter 4 — A Tender Father

All 7 questions

Read Chapter 4 of Gentle and Lowly. Primary Scripture: Psalm 103:8–14; Luke 15:11–32

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?

+ 6 more questions in the full guide

Chapter 5 — The Emotional Life of Christ

All 7 questions

Read Chapter 5 of Gentle and Lowly. Primary Scripture: John 11:1–44; Isaiah 53:3–4

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?

+ 6 more questions in the full guide

Chapter 6 — Struck Down, Not Destroyed

All 7 questions

Read Chapter 6 of Gentle and Lowly. Primary Scripture: 2 Corinthians 4:7–12; Isaiah 42:1–4

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?

+ 6 more questions in the full guide

Chapter 7 — He Can Deal Gently

All 7 questions

Read Chapter 7 of Gentle and Lowly. Primary Scripture: Hebrews 5:1–3; Hebrews 4:14–16

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?

+ 6 more questions in the full guide

Chapter 8 — The Persistent Priest

All 7 questions

Read Chapter 8 of Gentle and Lowly. Primary Scripture: Hebrews 7:23–25; Romans 8:34

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?

+ 6 more questions in the full guide

Chapter 9 — Able to Save to the Uttermost

All 7 questions

Read Chapter 9 of Gentle and Lowly. Primary Scripture: Hebrews 7:25; 1 Timothy 1:15–16

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?

+ 6 more questions in the full guide

Chapter 10 — Our Advocate

All 7 questions

Read Chapter 10 of Gentle and Lowly. Primary Scripture: 1 John 2:1–2; Romans 8:33–34

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?

+ 6 more questions in the full guide

Chapter 11 — Compassions New Every Morning

All 7 questions

Read Chapter 11 of Gentle and Lowly. Primary Scripture: Lamentations 3:22–23; Exodus 34:6–7

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?

+ 6 more questions in the full guide

Chapter 12 — His Ways Are Not Our Ways

All 7 questions

Read Chapter 12 of Gentle and Lowly. Primary Scripture: Isaiah 55:6–9; Hosea 11:8–9

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?

+ 6 more questions in the full guide

Chapter 13 — Rich in Mercy

All 7 questions

Read Chapter 13 of Gentle and Lowly. Primary Scripture: Ephesians 2:1–7; Romans 5:20

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"?

+ 6 more questions in the full guide

Chapter 14 — Drawn In

All 7 questions

Read Chapter 14 of Gentle and Lowly. Primary Scripture: Song of Solomon 1:2–4; Jeremiah 31:3

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?

+ 6 more questions in the full guide

Chapter 15 — The Emotional Life of the Father

All 7 questions

Read Chapter 15 of Gentle and Lowly. Primary Scripture: Zephaniah 3:17; Isaiah 62:4–5

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?

+ 6 more questions in the full guide

Chapter 16 — Nothing Can Separate Us

All 7 questions

Read Chapter 16 of Gentle and Lowly. Primary Scripture: Romans 8:31–39

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?

+ 6 more questions in the full guide

Chapter 17 — Christ With Us in the Darkness

All 7 questions

Read Chapter 17 of Gentle and Lowly. Primary Scripture: Psalm 23; Isaiah 43:1–2

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?

+ 6 more questions in the full guide

Chapter 18 — All Authority

All 7 questions

Read Chapter 18 of Gentle and Lowly. Primary Scripture: Matthew 28:18–20; Philippians 2:9–11

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?

+ 6 more questions in the full guide

Chapter 19 — He Who Began a Good Work

All 7 questions

Read Chapter 19 of Gentle and Lowly. Primary Scripture: Philippians 1:6; John 10:27–29

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?

+ 6 more questions in the full guide

Chapter 20 — The Exploding Heart

All 7 questions

Read Chapter 20 of Gentle and Lowly. Primary Scripture: Ephesians 3:14–19; John 17:24–26

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?

+ 6 more questions in the full guide

Review & Reflection

All 8 questions

Review your notes, journal entries, and highlighted passages from the entire book

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?

+ 7 more questions in the full guide

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About the Gentle and Lowly guide

How many weeks is the Gentle and Lowly study guide?

This study guide covers Gentle and Lowly in 22 weeks, with week-by-week discussion questions, reading references, and closing prayers for each session.

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The complete guide includes 155 discussion questions across 22 weeks — an average of 7 questions per week, designed for group conversation.

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Yes — the questions are written for group discussion and work well for small groups, book clubs, church studies, and couples reading together.

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