When you’ve been friends with someone for years (even decades), you probably think you’ve heard all their stories, laughed at all their jokes, and witnessed all their shining moments. (Of course, you’ve seen—and supported—them at less than their best, too.)
But no matter how well you think you know your squad, you can always dig a little deeper. How? Ask your friends some questions that go way beyond the run-of-the-mill “How was your day?” and “Wanna get brunch this weekend?” (The answer’s always yes, anyway.)
The first way to do this, according to Anna Akbari, PhD, a sociologist and former professor in the department of media, culture, and communication at New York University, is to ask your friends questions about their past so you can get a better picture of where they came from. “We too often assume that everyone has had the same experiences that shaped them that we have… We all have different wounds that we carry with us,” she explains. “So the more you can understand that person’s history, the more empathetic you can be for them.”
The second approach, she says, is asking future-minded questions. “That helps you to really understand what they’re working toward, or their idealized vision for their identity and their life,” Akbari explains. “And that can also help you be perhaps less critical of some of the decisions they’re making.” Plus, asking about their future goals—which, btw, might’ve changed since you met—can also help you to give your friend better advice so, ya know, they can actually achieve them.
Ultimately, Akbari says, “Paying attention to both of those things can bring you deeper—and create a stronger, more understanding, more empathetic, more loving relationship.”
Of course, you don’t have to ask all these questions at once (unless you want to do it at a sleepover, like in the good ole days). You took time developing your friendships, so it only makes sense that you take some time to deepen them. These are the best questions to ask your friends:
1. What’s your favorite childhood memory?
2. Do you have any regrets? If so, what are they and why?
3. If you could change anything about your past, would you and what would it be?
4. What’s the best advice a family member gave you growing up?
5. What was the worst advice?
6. How would you describe your childhood home?
7. What did you fear most growing up, and do you still fear that?
8. Who was your first celebrity crush?
9. How did you deal with past disappointments?
10. What was your first dream job, and is it still your dream job?
11. Who was your role model growing up?
12. If you had a childhood pet and they passed away, how did you handle that?
13. Have you ever given up on a dream? What was it?
14. How has your relationship with your parents changed?
15. What’s your proudest moment?
16. When have you felt the most challenged?
17. Who has been a big influence on you?
18. What’s the weirdest thing you believed as a kid?
19. If you could relive any moment in your life, would you? Which one?
20. What’s the hardest lesson you’ve ever had to learn?
21. How have your values changed over time?
22. Would your younger self be proud of where you are in life now?
23. What was your first impression of me when we met?
24. Have you ever lost a friend? If so, why?
25. What’s the biggest mistake you’ve ever made?
26. Do you have any weird habits that I don’t know about?
27. What’s your earliest memory?
28. Who was your first kiss with, and did you enjoy it?
29. If you could change one thing about yourself, would you?
30. Have you ever had a “life-changing” moment? If so, what was it?
31. What’s the #1 thing on your bucket list?
32. Do you believe in having a five-year plan?
33. If you can only accomplish one thing in your life, what would it be?
34. What’s your biggest career goal?
35. Do you worry about your future, or take things as they come?
36. How have your past experiences shaped your view of the future?
37. Are you afraid to grow older or excited?
38. If you could travel anywhere in the world (all expenses paid), where would you go?
39. Do you want to have kids someday? If so, how many?
40. How do you define success for yourself?
41. What’s more important to you: work life or personal life?
42. Who do you aspire to be like?
43. Are you happy where you’re living now, or do you plan to move?
44. When do you think you’ll know you’ve met “The One”?
45. What motivates you to go after your goals?
46. What do you hope to achieve by age 50, 60, 70, etc.?
47. If you had to move across the world for your dream job, would you?
48. How will you know you’ve “made it”?
49. Do you think we’ll always be friends?
50. Does anything keep you up at night? If so, what?
51. What’s the first thing you do in the morning, and how does it impact the rest of your day?
52. Do you think your priorities will change over time or generally stay the same?
53. If you found out today was your last day on Earth, what would you do?
54. What would you be willing to give up to achieve your dreams?
55. What are you most looking forward to this year?
56. When you make a resolution, do you stick to it?
57. If you had unlimited money to start your own business, what would it be?
58. How do you plan to spend your retirement?
59. What would you want to eat for your last meal?
60. If you had the opportunity to be immortal, would you take it?