38 Interesting Questions You Never Thought To Ask Your Friends But Should

Want to strengthen your friendships? Skip the superficial small talk and dive deeper with these questions.
These questions are bound to spark some good conversations that can help you reconnect with friends.
Yusuke Nishizawa via Getty Images
These questions are bound to spark some good conversations that can help you reconnect with friends.

If your friendships have been feeling distant, strained or just out-of-sync lately, you’re not the only one.

Americans report having fewer close friends, keeping in touch with friends less and relying less on them for emotional support than they once did, according to recent data from The Survey Center On American Life.

The truth is, friendships enrich our lives: they make us feel connected, lift our spirits when we’re down and even help us live longer. But maintaining close friendships does require some effort.

If you’ve been looking for ways to dig deeper with your pals, start here. The questions below can act as a gateway to more meaningful, interesting conversations that will bring you closer together.

With help from friendship coach Danielle Bayard Jackson (host of the “Friend Forward” podcast), counselor Suzanne Degges-White (professor and chair of the department of counseling and higher education at Northern Illinois University) and psychotherapist Deborah Duley (founder of the counseling practice Empowered Connections), we’ve compiled a list of 38 questions that will up-level your friendships.

Ask a few of these questions — or heck, all of them — during your next get-together, whether it’s over FaceTime or face to face.

1. What was your first impression of me when we met?

2. When did you realize we were going to be good friends?

3. What’s an unpopular opinion that you have?

4. When’s a time you laughed so hard you cried?

5. What, if anything, do you miss about being a kid?

6. What were you like in middle school?

7. What other job or career do you think you’d be really good at?

8. What’s an album you could listen to from beginning to end?

9. What did you look like when you were younger? Show me a baby picture!

10. If you could rename yourself, what name would you choose?

11. When do you feel most in your element?

12. What’s the best birthday you ever had?

13. Do you have any recurring dreams — good or bad?

14. Which person in your life knows you the best?

15. What good quality of yours do you wish more people noticed?

16. What would you do with an extra hour in the day?

17. If you had $10,000 to donate to a cause or charity, which would it be?

18. What do you appreciate most about our friendship?

19. What’s one thing I could do to be a better friend to you?

20. What’s the most expensive thing you own? Was it worth the money?

21. What does your ideal Friday night look like?

22. When’s the last time you cried and why?

23. What’s a common misconception people have about you?

24. If the pandemic ended tomorrow, what’s the first thing you’d do?

25. What’s a recent win you’ve had that I can celebrate with you?

26. What keeps you up at night these days?

27. What are two changes you could make that would improve your life? Why haven’t you done them yet?

28. What cheers you up when you’re having a bad day?

29. What was your best sexual experience? And your worst?

30. If you had to pick a motto for your life, what would yours be?

31. What’s the last book you read? Would you recommend it?

32. Have you ever been admitted to the hospital? For what?

33. What was your first heartbreak?

34. What’s the scariest thing you’ve been through?

35. (If they have kids) What’s your secret hope for your child’s future? And what’s your secret fear?

36. Which actor would play you if they were making a movie about your life?

37. Have you ever lied for a friend or asked a friend to lie for you? What were the circumstances?

38. Where would you want to retire and why?

Friendships ebb and flow throughout our lives, but these days, it may feel like all they do is ebb. Friend Zone is a HuffPost series that features reflections on the nature of our friendships and what we can do to maintain and strengthen them — plus, how to know when it’s time to let them go.

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