13-Week Study & Discussion Guide

Single. Dating. Engaged. Married.

by Ben Stuart·92 discussion questions

Week 1 — FreeRead the Introduction of Single, Dating, Engaged, Married. Key passages: Ecclesiastes 3:1-8; Jeremiah 29:11

Discussion question your group will work through:

1.Stuart opens by observing that even in a hyper-connected culture, loneliness is epidemic. Have you felt this tension personally — surrounded by social connection yet still feeling relationally alone? What do you think is driving it?

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About This Study Guide

Single, Dating, Engaged, Married by Ben Stuart is a practical and theologically grounded guide to navigating the four major seasons of relational life. Stuart's central thesis is that God is not absent from any stage of your love life — He has intentions, purposes, and gifts built into each one. Rather than treating singleness as a waiting room, dating as a minefield, or marriage as a finish line, Stuart invites readers to ask a better question: not "How do I get to the next stage?" but "How do I thrive — for God and for others — right where I am?" Drawing on Scripture, honest cultural observation, and pastoral warmth, Stuart walks through singleness, dating, engagement, and marriage as distinct seasons, each with its own beauty, its own dangers, and its own callings. This updated edition also includes a new chapter on how to end dating relationships well — a topic rarely addressed with this much care and wisdom.

This study guide is designed for small groups or individuals who want to engage the book slowly, prayerfully, and honestly. Each week corresponds to one chapter or section of the book. The suggested rhythm is simple: read the assigned chapter before your group meets (or before your personal study time), journal your initial responses to one or two questions, then work through the discussion questions together — or alone, speaking them back to God. You don't need theological training to benefit from this guide; you just need a willingness to be honest about where you actually are.

By the end of this guide, you can expect to have a clearer sense of how God views your current relational season, a more biblically grounded framework for pursuing (or preparing for) relationships, and — perhaps most importantly — a deeper conviction that your life right now, in this season, is not on hold. God is at work. This guide is an invitation to pay attention.

Week 1: Introduction — Navigating the Seasons

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Read the Introduction of Single, Dating, Engaged, Married. Key passages: Ecclesiastes 3:1-8; Jeremiah 29:11

1.Stuart opens by observing that even in a hyper-connected culture, loneliness is epidemic. Have you felt this tension personally — surrounded by social connection yet still feeling relationally alone? What do you think is driving it?

2.The book's premise is that God has a purpose for each relational season, not just for marriage. How does that idea strike you? Does it feel like good news, or does part of you resist it — and why?

3.Stuart is writing primarily to young adults who want to be married but aren't sure how to get there wisely. Even if that's not your exact situation, what do you hope to gain from working through this book?

4.The introduction frames the four seasons — single, dating, engaged, married — not as a ladder to climb but as distinct callings to steward. What would change about your current season if you genuinely believed God had placed you there on purpose?

5.Stuart notes that most single adults still want to be married, even as marriage rates decline. What cultural messages have you absorbed about marriage — is it ultimate fulfillment, an outdated institution, or something else? Where do those messages come from?

6.Ecclesiastes 3 reminds us there is a season for everything. How have you typically responded to seasons of life that felt "wrong" — seasons you didn't choose or didn't want? What would it look like to receive your current season as a gift rather than a burden?

7.What is one specific question or fear about relationships that you hope this book addresses? Share it with your group — or write it in your journal — so you can return to it at the end.

Week 2: Chapter 1 — The Goodness of Singleness

All 7 questions

Read Chapter 1 of Single, Dating, Engaged, Married. Key passages: 1 Corinthians 7:32-35; Matthew 19:10-12

1.Stuart argues that singleness is not simply the absence of marriage but a season with its own God-given purpose. How does that reframe the way you (or people you know) typically talk about being single?

+ 6 more questions in the full guide

Week 3: Chapter 2 — Singleness and Mission

All 7 questions

Read Chapter 2 of Single, Dating, Engaged, Married. Key passages: Matthew 28:18-20; Romans 12:1-2

1.Stuart connects singleness to the Great Commission — arguing that single people have a unique mobility and availability for mission. Does thinking about your singleness in missional terms feel natural or foreign to you?

+ 6 more questions in the full guide

Week 4: Chapter 3 — The Purpose of Dating

All 7 questions

Read Chapter 3 of Single, Dating, Engaged, Married. Key passages: Proverbs 4:23; 1 Thessalonians 4:3-8

1.Stuart defines the purpose of dating clearly: it is the process of prayerfully and wisely evaluating someone for marriage. How does that definition compare to the way you or your culture typically thinks about dating?

+ 6 more questions in the full guide

Week 5: Chapter 4 — Dating with Purity

All 7 questions

Read Chapter 4 of Single, Dating, Engaged, Married. Key passages: 1 Corinthians 6:18-20; Song of Solomon 2:7

1.Stuart argues that the Christian vision of sexuality is not primarily a list of rules but a high and beautiful vision of what sex is for. In your own words, what is that vision? Does it feel compelling to you?

+ 6 more questions in the full guide

Week 6: Chapter 5 — How to End a Dating Relationship Well

All 7 questions

Read Chapter 5 of Single, Dating, Engaged, Married. Key passages: Matthew 7:12; Ephesians 4:15

1.Why do you think the topic of breaking up is so rarely addressed in Christian books and conversations about dating? What does that silence communicate?

+ 6 more questions in the full guide

Week 7: Chapter 6 — Engagement: The Purpose of the Season

All 7 questions

Read Chapter 6 of Single, Dating, Engaged, Married. Key passages: Ruth 3-4; Proverbs 24:27

1.Stuart defines engagement as a season of intentional preparation for marriage — not just wedding planning, but life preparation. How does that definition compare to how most engaged couples you know have approached it?

+ 6 more questions in the full guide

Week 8: Chapter 7 — Engagement: Preparing for Marriage

All 7 questions

Read Chapter 7 of Single, Dating, Engaged, Married. Key passages: Ephesians 5:22-33; Genesis 2:18-25

1.Stuart identifies several key areas that engaged couples must discuss and align on before marriage — finances, family of origin, faith, future goals. Which of these conversations do you think is most commonly avoided, and why?

+ 6 more questions in the full guide

Week 9: Chapter 8 — The Foundation of Marriage

All 7 questions

Read Chapter 8 of Single, Dating, Engaged, Married. Key passages: Genesis 1:26-28; Matthew 7:24-27

1.Stuart argues that many marriages crumble not because they lacked love at the start, but because they lacked the right foundation. What does he identify as the only foundation strong enough to hold a marriage — and why does that matter before anything else?

+ 6 more questions in the full guide

Week 10: Chapter 9 — Roles in Marriage

All 7 questions

Read Chapter 9 of Single, Dating, Engaged, Married. Key passages: Ephesians 5:22-33; 1 Peter 3:1-7

1.Stuart argues that the biblical vision of roles in marriage is not about hierarchy of worth but about difference in function — and that it is ultimately a picture of the gospel. How does he explain that connection? Do you find it convincing?

+ 6 more questions in the full guide

Week 11: Chapter 10 — Communication and Conflict in Marriage

All 7 questions

Read Chapter 10 of Single, Dating, Engaged, Married. Key passages: Ephesians 4:25-32; James 1:19-20

1.Stuart argues that most marital conflict is not really about the surface issue (money, chores, schedules) but about something deeper — unmet needs, unspoken fears, or misaligned expectations. Have you observed this pattern? How does recognizing the deeper issue change how you approach conflict?

+ 6 more questions in the full guide

Week 12: Chapter 11 — Marriage and Mission

All 7 questions

Read Chapter 11 of Single, Dating, Engaged, Married. Key passages: Genesis 1:28; Acts 18:2, 18, 26 (Priscilla and Aquila)

1.Stuart argues that a marriage turned entirely inward — consumed with each other and with personal happiness — is both unsatisfying and unfaithful to God's design. Why do you think so many marriages become self-contained rather than outward-facing?

+ 6 more questions in the full guide

Week 13: Review & Reflection

All 8 questions

Review your notes from all chapters of Single, Dating, Engaged, Married. Key passage: Philippians 1:6

1.Looking back across the whole book: which chapter or season spoke most directly to where you are right now — and what did it say that you most needed to hear?

+ 7 more questions in the full guide

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This study guide covers Single. Dating. Engaged. Married. in 13 weeks, with chapter-by-chapter discussion questions, reading references, and closing prayers for each session.

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The complete guide includes 92 discussion questions across 13 weeks — an average of 7 questions per week, designed for group conversation.

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