Book Club Questions for Single. Dating. Engaged. Married.

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?

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?

2.Paul's words in 1 Corinthians 7 suggest that a single person has an undivided devotion to God that a married person cannot fully replicate. Do you find that compelling, or does it sound like a consolation prize? Be honest.

3.Stuart points to Jesus and Paul as examples of single people who changed the world. How does looking at their lives challenge the assumption that a person can't fully flourish or make their greatest impact until they're married?

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?

2.He draws on examples of single men and women throughout church history who made enormous kingdom impact precisely because they were unattached. Who are some of those figures, and what is it about their lives that strikes you most?

3.Stuart challenges single people not to drift through this season but to invest it intentionally. What does intentional kingdom investment look like for a single person in your specific context — your city, your workplace, your campus?

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?

2.He describes two unhealthy extremes in Christian dating culture — those who treat dating too casually (serial dating with no intentionality) and those who treat it with paralyzing seriousness (afraid to date anyone they couldn't immediately marry). Which extreme are you more prone to, and why?

3.Stuart argues that clarity — knowing what you are looking for — is essential before you start dating. What does he say you should be looking for in a potential spouse? Do you have that kind of clarity yourself?

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?

2.He grounds the call to purity in the doctrine of the body — that your body is a temple of the Holy Spirit and was bought at a price. How does that theological foundation change the conversation from "How far is too far?" to something more substantial?

3.Stuart is honest about the power of sexual desire and does not treat it as shameful in itself — he treats it as a good gift pointed in the wrong direction when misused. How does distinguishing between the desire (good) and the misuse (harmful) help you think more clearly about purity?

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?

2.Stuart argues that ending a dating relationship well is an act of love and integrity, not just a necessary evil. What does "ending well" actually look like, according to this chapter? What are the key elements?

3.He addresses the temptation to "slow fade" — gradually withdrawing rather than having a direct, honest conversation. Why is the slow fade so tempting? And what makes it ultimately more harmful than a hard conversation?

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?

2.He argues that one of the greatest dangers of engagement is treating it as an emotional high to be enjoyed rather than a window for honest evaluation. What are the hard questions that should be asked during this season, and why do so many couples avoid them?

3.Stuart draws on the story of Ruth and Boaz as a model of a relationship that moved through distinct stages with integrity and purpose. What stands out to you about how Boaz pursued Ruth — particularly the way he took initiative, acted with honor, and was guided by wise counsel?

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?

2.He argues that understanding your own "family of origin" patterns — the relational habits and wounds you carry from your upbringing — is essential preparation for marriage. What patterns (healthy or unhealthy) have you absorbed from your family that you would need to be aware of going into a marriage?

3.Ephesians 5 presents marriage as a picture of Christ and the church — the husband's love reflecting Christ's self-giving sacrifice, the wife's respect reflecting the church's trusting response. How does this vision of marriage as a living parable change the stakes of what you're preparing for?

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?

2.He traces marriage back to Genesis 1 and the creation of humanity in God's image — male and female together reflecting something of God that neither can reflect alone. What does that "image-bearing together" language say about what marriage is fundamentally for?

3.Jesus' parable of the wise and foolish builders (Matthew 7) is about hearing and doing — not just knowing the right things but building on them. What does it look like to actually build a marriage on Christ rather than just using Christian language about it?

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?

2.He describes the husband's role of headship through the lens of Ephesians 5 — not domineering authority but self-sacrificial, servant leadership in the pattern of Christ. What does that kind of leadership actually look like in day-to-day married life? What does it not look like?

3.Stuart describes the wife's role in terms of 1 Peter 3 and Ephesians 5 — a willing, trusting response that is itself an act of strength, not weakness. How does the analogy of the church's relationship to Christ reframe what it means for a wife to respect and follow her husband?

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?

2.He draws on Ephesians 4 — "speak truth in love," "don't let the sun go down on your anger" — as a framework for healthy conflict. What does it mean in practice to speak truth AND love at the same time? Which one do you tend to sacrifice when conflict heats up?

3.Stuart addresses different conflict styles — those who escalate (attack) and those who withdraw (go cold). Which pattern do you tend toward, and what is it rooted in?

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?

2.He holds up Priscilla and Aquila from Acts as a model of a couple on mission together — hosting a church in their home, discipling Apollos, working alongside Paul. What is striking to you about how they used their marriage as a vehicle for the kingdom?

3.Stuart connects back to the creation mandate in Genesis 1:28 — "be fruitful and multiply, fill the earth and subdue it" — as a mandate for married couples to expand the kingdom together. What does that mission look like in your specific context today?

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?

2.Stuart's consistent refrain is that God has a purpose for every relational season. Has reading this book changed the way you see your current season? If so, how — and if not, what is still holding you back from that shift?

3.Which idea or argument in the book did you find most challenging or hardest to accept? Have you come to a place of peace with it, or is it still unresolved? Share that honestly with your group.