50 Questions To Ask Your Boyfriend That Will Bring You Closer Together

Thought Catalog
3 min readJun 13, 2022

By Chrissy Stockton

1. What quality do you most hope your future children possess?

2. What accomplishment are you most proud of?

3. Who has it easier: our generation or our parent’s?

4. What place you’ve traveled to has changed you as a person?

5. What fictional character do you most relate to?

6. What song would be the theme song if you had your own show?

7. What was your favorite book as a child?

8. What’s the scariest thing you’ve ever experienced?

9. What is your earliest memory?

10. What do you want to do differently than your parents?

11. What do you wan to do the same as your parents?

12. What is your perfect day?

13. What’s something I would be surprised to find out about you?

14. What’s an experience you never, ever want to repeat?

15. What technology can you not live without?

16. Are you closer to your mother or your father?

17. What has been the best thing about the last year of your life?

18. What has been the most frustrating thing about the last year of your life?

19. Where is your favorite place in the world?

20. Who is the best superhero?

21. How would you survive the zombie apocalypse?

22. What are you most likely to be arrested for?

23. What’s your favorite time of day?

24. What is the first thing you would do if you won the lottery?

25. What is something you’d like to change about yourself?

26. What is your funniest dating story?

27. What is the most embarrassing thing that’s happened to you?

28. What is your favorite family tradition?

29. What did you want to be when you grew up?

Thought Catalog

We’re a community of creators based in NYC. We publish a digital magazine and limited edition books. thoughtcatalog.com // shopcatalog.com