36 Questions to Ask Your Best Friend

36 Questions to Ask Your Best Friend

In most parts of the country, February is a dark, dreary month made brighter by vibrant chocolate boxes, big red hearts, and long-stemmed roses. All of these symbols are ushered in to help us celebrate Valentine's Day, a universal toast to those in romantic relationships. 

Valentine's Day can leave single people feeling left out, to say the least. And while we've gotten a lot better at celebrating self-love over the years—and many of us are even learning how to date ourselves!—it isn't often that we pause to celebrate what is arguably one of the most important relationships of our lives: The one we have with our best friend. 

In the spirit of the New York Times' 36 Questions that went viral in 2015, we compiled a list of 36 questions to ask your best—or very close—friend. Because Valentine's Day isn't just for couples, or even for self-love. It's for our friends, too. And who knows—through these questions, you may just find that you don't actually know everything about your best friend.  

36 Questions to Ask Your Best Friend

1. Of all the things in your life, what are you most grateful for? 

2. What do you appreciate the most about out friendship?

3. When you can't sleep at night, what are you usually thinking about?

4. Do you want kids? Why or why not?

5. If you already have kids, what's your favorite aspect of parenthood? Least favorite?

6. If you could live in any decade, which one would you choose?

7. What's your favorite memory of our friendship as a whole?

8. Favorite memory of our friendship in the last year?

9. Do you have any regrets? What are they?

10. What's the best gift you've ever received?

11. What is your love language? 

12. When you're upset, how do you typically like to be comforted?

13. What was the hardest moment of your life?

14. When do you feel the most fulfilled?

15. Who do you feel most inspired by? 

16. If you had a day when you could absolutely anything you wanted, what would you do?

17. What are some of the things you still want to accomplish in your life?

18. What do you want people to know about you?

19. What do you consider to be your most embarrassing moment?

20. What do you consider to be your top coping mechanism?

21. Who do you see as the earliest positive influence in your life?

22. What's the best place you've ever visited? Wha did you love about it? 

23. If you didn't have your current job, what would you be doing instead?

24. If your partner didn't like me, what would you do?

25. In general, are you happy?

26. Do you have a secret talent I don't know about?

27. What makes your life feel purposeful?

28. What do you most look forward to doing with me in the future?

29. What would your dream vacation with me look like?

30. How can I better show my appreciation for our friendship?

31. Have you ever kept anything from me? If so, why? 

32. Do you struggle with anxiety?

33. Can you tell me your life story in three minutes? (You can set a timer for this one.)

34. What does love mean to you? 

35. Would you ever want to be famous? If so, in what way?

36. If you could have dinner with anyone, dead or alive, who would it be? 



Want more great blog posts? Give these ones a read: 

Back to blog

Leave a comment

Please note, comments need to be approved before they are published.