Romantic Questions to Ask Your Boyfriend | Deep Questions to Ask Your Boyfriend

Date nights for established couples can feel boring and stale if you talk about the same old topics all the time. Talking about work, the kids or household repairs should not be the primary focus of nights when you’re trying to reconnect as a couple.

So, here is a list of 100 — yes, 100 — questions that you can choose from to ask each other on your next dinner out.

Use only two to three questions per date night, and really talk about the answers in depth. They range across various domains, including romance, intimacy, family, career, and many others.

Questions:

  1. What makes you feel the most loved?
  2. What’s your dream date night?
  3. What’s your favorite romance movie?
  4. What’s your favourite meal to cook for date night?
  5. What kind of music puts you in the mood?
  6. What’s the number one thing that you think makes a relationship last?
  7. What do you love most about me?
  8. What setting do you think makes the perfect date night atmosphere?
  9. What physical action or gesture do you find romantic?
  10. Who do you think makes a great example for a relationship and why? (Can be a celebrity couple or someone you know.)
  11. What was your first impression of me when we met?
  12. If you had your choice for date night would you rather 1) stay at home and have a candlelit dinner, 2) Dress up and go to a concert, or 3) explore the great outdoors and go on a hike together?
  13. What physical feature of mine is your favorite?
  14. What’s your favorite way I touch you?
  15. If you could travel anywhere in the world with me with no monetary restrictions, where would we go?
  16. What song do you think of when you think of me?
  17. Is there anything about me you might not know but want to know?
  18. If you could describe me in only one word, what would it be?
  19. What was your favorite part about our first kiss?
  20. When and what was the first moment you knew you were in love with me?
  21. What’s your most favorite outfit I wear?
  22. What’s your favorite restaurant for date night?
  23. What could I do to improve our relationship?
  24. What about me first attracted you?
  25. What’s been one of the funniest times we’ve had together?
  26. What do you say to others when you talk about me?
  27. Why do you think we met each other?
  28. When was the first moment you wanted to kiss me?
  29. What do you think I find most attractive about you?
  30. What do I do that helps you calm down?
  31. Is there anything I can do to help you feel more special?
  32. What’s one thing you want to do with me that we haven’t done yet?
  33. When are you the happiest with me?
  34. What great adventures do you think we’ll achieve in the next 5 years?
  35. What values do you think are most important in a relationship?
  36. What do you like best about our relationship?
  37. Is there anything you’re afraid to accomplish that I can help you with?
  38. Is there anything you’d like me to be willing to change?
  39. Has anything surprised you about our relationship?
  40. What can I do to encourage you on a regular basis?
  41. What strengths do you see in our relationship?
  42. What weaknesses do you see in our relationship?
  43. What goals would you like to set for our relationship?
  44. What do you think is most important for communicating in our relationship?
  45. What’s been the most memorable moments we’ve had together (other than our wedding day)?
  46. What can I do to spice up our love life?
  47. Would you rather receive the most amazing massage you’ve ever had in your entire life from me or have me pour my heart and soul out in the most beautiful poem you’ve ever read?
  48. What’s your most scandalous memory of us?
  49. What moment would you want to relive again and again?
  50. What is something little I do that makes you smile?

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