56 Questions to Ask at Dinner With Friends

1. What's a super common thing you've never done or experienced?

2. What's the biggest scam that's commonly accepted?

3. What’s the weirdest thing you did in the early part of the pandemic?

4. What was your worst summer job experience?

5. If you could choose anyone, who would you have narrate your inner monologue?

6. What's your favorite pair of sneakers? 

7. Amazon or Apple?

8. What was your first job—and how much did you make?

9. What's the farthest you've been from home?

10. You're at brunch with your friends. What do you say to start a fight?

11. What are you reading right now?

12. What's one thing you know way, WAY too much about?

13. You're on a blind date. What would they have to say for you to up and leave?

14. What corporate buzzwords/phrases make your skin crawl?

15. What was your first job, and what are you doing now?

16. What's something a doubter said to you that actually motivated you to prove them wrong?

17. What product are you obsessing over right now?

18. What's a movie or TV show you regrettably finished?

19. If you opened up your fridge, seeing what item would make you the most happy?

20. What was your first AIM screen name?

21. What's a fringe company or technology that could be mainstream in a few years?

22. What's something you learned as an adult that blew your mind?

23. What's one splurge you spring for that makes you feel rich?

24. Would you date a coworker?

25. How old do you feel, and how old are you actually?

26. What rabbit hole did you go down most recently?

27. What's the most miserable experience that you wish a startup would solve?

28. What's something you buy from the grocery store but never finish?

29. What purchase would make your inner child happy?

30. You're given the choice of $1 million in cash, bitcoin, or stock of your choice. Which are you taking?

31. What brand are you always loyal to?

32. You just got a huge bonus at work. Congrats. What're you spending big on?

33. What non-athletic event would you gold medal in?

34. You want to do a heist. who's your dream partner in crime?

35. What was your favorite show to watch on Saturday mornings?

36. What's the best piece of advice a manager ever gave you?

37. Everyone loves dunking on Facebook. What are some other things you love to hate?

38. What is the book you say is your favorite and what is your actual favorite?

39. What is the best potato chip flavor — BBQ, Plain, Sour Cream & Onion, Salt & Vinegar?

40. What is the most outrageous hill you will die on?

41. What's your go-to Wordle starting word?

42. You have 12-months to turn $10 into $10 million. Who are you partnering with?

43. Would you take a $70k/week job offer where you get paid to sit in a pitch-black room and do nothing for 10 hours a day?

44. Would you rather have: 1 bitcoin or 60 shares of Tesla?

45. What is a simple habit you adopted that changed your life?

46. What are the biggest red flags you've seen in a boss you've had?

47. What is the best business/finance movie ever made?

48. Without saying the name of your state, where do you live?

49. What is something that lots of people feel guilty spending money on, but shouldn't?

50. What is one company you are convinced you could do a better job at running than the current CEO?

51. If you could tell your younger self any one thing, what would it be?

52. What was cool when you were a kid, but isn’t cool now?

53. One’s gotta go: Twitter, TikTok, Instagram, Reddit — which one do you pick?

54. You're given the choice of $1 million in cash, bitcoin, or stock of your choice. Which are you taking?

55. Which stock is making you money today?

56. What's something you learned embarrassingly late?