Whether you have been dating your significant other for weeks, months or years, there is always more to learn about one another. Next time you are on a date with your love, put down your phones and pull out this list. You may be surprised what you learn, and where the topics lead!

  1. What are 5 things you hope to be remembered for?
  2. What are 5 passions you have and why?
  3. Describe your family dynamic of your childhood verses your family dynamic now.
  4. What are 3 things that make you happy?
  5. What popular thought or notion do you think the world has most wrong?
  6. What is one thing I don’t know about you?
  7. What are two things I do well?
  8. How have you seen me change since we’ve been together?
  9. How have you changed in the time we’ve been together?
  10. What is one thing you want to do different from your parents?
  11. What is your favorite memory of us together?
  12. If you had to live in another country, where would you go?
  13. What is my most difficult challenge right now?
  14. What is your most difficult challenge right now?
  15. Excluding money or time, what is one thing that I wish I could have?
  16. If you could be an expert in anything, what would it be?
  17. Name 3 things on your bucket list.
  18. What are your favorite qualities in me?
  19. How would you spend 1 million dollars?
  20. What is the greatest strength and weakness of our relationship?
  21. What is your 5-year plan? 10-year plan?
  22. If you never had to work again, what would you do with your life?
  23. If you could choose one mentor – famous or not – who would it be?
  24. What is your biggest pet peeve?
  25. When you met me, what was your first impression? Was it correct?

I love lists like this because they take us out of our comfort zone. Asking questions like these can be beneficial at any stage of a relationship. In the beginning, when everything is new and exciting, we tend to hang on every piece of new information as we learn about one another. After a while, tossing in conversation topics like these keep things fresh and fun.

Ask away!

Chels