52 Date Night Questions

One of the main goals of this little date night experiment in marital bliss was to cultivate depth through intentional questions that fuel discussion. This is what we both loved when we were dating and it can quickly lose steam in marriage if you’re not careful. So, here are our 52 most favorite date night questions to cultivate depth and oneness amongst each other.

52 Date Night Questions

  1. What is one word you would use to describe our marriage?
  2. What is your favorite book and why?
  3. What is your favorite Starbucks drink? Or what drinking are you wanting to try?
  4. What is one adjustment I could personally make so I can be more sharpening and helpful for you?
  5. What is one thing you wish you would have done differently during the past year?
  6. What is one thing you want to do differently in the upcoming year?
  7. If you could read any book (or series) anywhere in the world, what book and where?
  8. If you could be a professional chef in any city, what city would that be and why?
  9. If you could dine upscale anywhere in the world, where would it be and why?
  10. If you could meet three people, dead or living, who would they be?
  11. When you were younger, what was your most embarrassing memory?
  12. What are a few things you got in big trouble for when you were younger?
  13. What are you most looking forward to in the coming weeks?
  14. What are some things burdening your mind that I can take care of this week?
  15. What are you most looking forward to heading into the upcoming Season (Fall, Spring, etc.)?
  16. What is your top ten list of the most romantic love songs ever?
  17. What is the hardest task you have ever done to this point in your life?
  18. With vacation approaching, what are a few things you are really excited to do?
  19. Over the next few weeks, what are ways we can deepen as friends?
  20. What is a funny, and not often talked about, memory from our dating story?
  21. What are a few family adventures I can create in the coming weeks/months? — i.e. home projects, trilogies to watch, trip to take, etc.?
  22. What is your funniest family vacation memory?
  23. What are your dream family vacations for us in the our future?
  24. Is there a craft or skill you would like for me to cultivate in the coming years?
  25. If we snuck off to a concert, who would you want to see?
  26. What is the best restaurant we have dined at since we’ve been married?
  27. Since we have been married, what is the best hotel we have stayed at?
  28. What is the most humbling experience you’ve had in the past year?
  29. What is your most embarrassing memory from High School or College?
  30. What is one way I can serve you in a more helpful way?
  31. If you could pick up any hobby, be really good at it, and have unlimited funds to engage in that hobby, what would it be?
  32. Would you rather vacation in the mountains or on the beach for the rest of your life?
  33. If you could be a character in any book, what character and why?
  34. What is one adjustment you really want to make before the end of the year?
  35. What are a few date night activities you would want to do?
  36. How can I help you prepare emotionally, financially, and personally for the holiday season?
  37. What five movies would you want to have forever if stranded on a desert island?
  38. If you could time travel to any time in your life, what event would you travel to?
  39. What was your favorite memory from our wedding?
  40. What is you absolute dream job?
  41. What events and details would you like included in our upcoming anniversary celebration?
  42. If you could give one or two encouragements to me, what would they be?
  43. What are a few projects/tasks you’re most excited about accomplishing this year? Anyway I can help?
  44. If you could buy one thing from Best Buy (money not an issue) what would you get?
  45. What spontaneous city would you like to visit this year?
  46. What was the best Halloween costume you ever wore?
  47. What is something you have been nervous/anxious about this past week?
  48. What are your favorite things about our marriage?
  49. What is one thing that I can do from week to week to make your life easier?
  50. If you could have a gift card to any store where would you want it to be?
  51. What is the best Christmas gift you have ever received from me?
  52. What is your favorite quote?

52 Date Night Questions