21 Brutal Questions to Ask Before You Say "I Do"

Love feels effortless when you're in the first flush of it. Marriage? That's forged in hard questions, cracks, and the courage to answer honestly. Don't wait for a crisis to ask what matters. Ask now.

Why These Questions Matter

A 2018 Journal of Marriage and Family study found that couples who clarify expectations about money, roles, and conflict before marriage are significantly less likely to divorce. That isn't a guarantee—but it's a fighting chance. These aren't conversation starters. They're risk management. They dig into values, scars, and hope.

The 21 Questions

1. How do we fight—and how does it end?
2. What does "cheating" mean to you?
3. Who controls money? Do we combine it or keep parts separate?
4. Do you want kids? When? How many?
5. What role does faith play in your life?
6. What's the secret you were never told to tell?
7. How involved should our families be?
8. How do you show love when you're hurting?
9. Where's your boundary with work after dark?
10. How do you apologize when you're wrong?
11. What health issues worry you—and how will we manage them?
12. What's your legacy vision for us in ten years?
13. How do we talk about sex, desires, and boundaries?
14. What happens if one of us betrays the other?
15. How do you want me to support your dreams?
16. If life breaks us, how do we try to rebuild?
17. Where is privacy okay—and where is it betrayal?
18. How do you cope under pressure or trauma?
19. What do you expect when grief enters our lives?
20. How much silence kills—and how much space heals?
21. What promise do you want us to protect above all else?

How to Use These Questions

Don't sprint through them. Choose one per week. Journal your own answers first. Then revisit the list in five or ten years. Let the conversation evolve as your marriage does.

Books That Breathe These Questions

These questions aren't theoretical. In The Grass Is Always Greener, marriage sits under pressure—where secrets, betrayal, and love collide. In They Never Came Home, loyalty, silence, and moral weight test a teen's heart.

Want more thought-provoking stories? Visit the Books page.