I’m passionate about the intersection of entrepreneurship and marriage. Entrepreneurship is lonely when things aren’t good at home, and having been a serial entrepreneur over the decades, this rings true for me. So, here’s an idea for you. Plan to spend one wk/year on vacation with your spouse (no kids). Here are 50 questions can ask each other year over year when it is just the two of you. You likely won’t get thru all of them each year, but it’s a great way to refocus your relationship with each other.
1. If you could relive a year in our relationship , what year would you choose? Why?
2. What is something you would like us to do to invest in our marriage this year?
3. What about our relationship makes you really sad?
4. What about our relationship makes you really sad?
5. What’s my biggest failure as a partner?
6. When are you the happiest?
7. What are you most excited about in our relationship during this season?
8. What would like for us to do differently from here to the end?
9. What’s your dream date night or weekend with me?
10. What were some things we used to do before we were married that you miss now?
11. What’s something you’d like to do together that we’ve never done? What makes it so inviting to you?
12. What was the last thing I did for you that you really enjoyed? What made it so pleasant for you?
13. When was a time you felt that I listened to you really?
14. What unspoken desires and wishes of yours would you like for me to fulfill?
15. What would be a perfect day for you?
16. What does quality time look like to you?
17. What is a time you have felt unheard or misunderstood?
18. Is there a couple you’d like to change places with for a day?
19. Where will we be in five years? 10? 20?
20. What bad habits have we fallen into that we’d like to change?
21. If you could trade a great quality with your spouse what would you trade?
22. What are you three favorite days of our marriage (excluding the obvious)?
23. What is the most favorite place we have visited together?
What’s the hardest thing you are dealing with right now?
24. What’s the most filling thing you are doing right now?
25. I f you had three wishes what would you wish for?
26. If I was more present with you what would you like for me to be doing while I do it? Be specific.
27. Given the choice of anyone in the world, whom would you want as a dinner guest?
28. What would constitute a “perfect” day for you?
29. For what in your life do you feel most grateful?
30. Is there anything on your ‘bucket list’ for us to plan toward? Would you like to make a plan?
31. If you could change anything about the way you were raised, what would it be?
32. If you could wake up tomorrow having gained any one quality or ability, what would it be?
33. If we were to create a morning routine, how would you like it to proceed?
34. If today was your last day on earth, what would you like to say to your children?
35. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
36. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
37. What is the greatest accomplishment of your life?
38. If you could change any behavior of mine, what would it be?
39. What do you value most in a friendship?
40. What is your most treasured memory?
41. What does friendship mean to you?
42. What are your unrealized expectations for our marriage you wish I’d dealt with differently? How would you like me to address them now?
43. Complete this sentence: “I wish I had someone with whom I could share … “
44. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone?
45. Your house, containing everything you own, catches fire. You have time to safely make a final dash to save any one item. What would it be?
46. What will be my legacy?
47. What matters most to you?
48. How much is enough?
49. What can I do differently to love you the way you want to be loved?
50. If you had a day to pamper yourself in the most decadent way you can imagine, what would it be like?
51. What about our relationship makes you really happy?
