Deep questions to ask your partner

You can live with someone for years and still not know about their hardest year or the opportunity they quietly turned down. These questions go to the decisions, fears and turning points that shaped your partner. None of them has a right answer.

Choose one question, not a list, and give it the whole evening if it needs it. Answer it yourself first so it feels like a trade.

1. What was a difficult year in your life that I don’t know much about?
2. What did you worry I would judge you for when we first met?
3. What is a decision you made that changed how you see yourself?
4. Have you ever turned down an opportunity without telling anyone it was offered?
5. Who did you spend too long trying to impress?
6. What promise turned out to be harder to keep than you expected?
7. Have you ever told someone to take a risk you weren’t brave enough to take yourself?
8. What did a past relationship teach you that I benefit from now?
9. What do we disagree about that you've never fully said out loud?
10. What part of your life feels most different from what you expected?
11. What is something you left behind that you still miss?
12. What did you once think you were bad at that you’ve since learned to do?
13. What did you agree to reluctantly that later became your preference?
14. What's the first sign you're more stressed than you're letting on?
15. What do you wish you'd asked your parents while you had the chance?
16. Who would you have called first with good news ten years ago, and would you call them now?
17. Have you ever taken someone’s side and later realized you hadn’t heard the whole story?
18. What is something you have changed your mind about in the past few years?