50 Questions You Should Ask Your Friends At Some Point In Time

You might think the only way to get to know someone—like, really know them—is by having a one-on-one convo full of deeply personal questions (or, at least, that’s what they say on The Bachelor). But the fun, silly questions you ask your friends can also be important—not just for strengthening your bond, but for your overall happiness.

Why? Well, imagine what hidden gems you might learn about your friends after they confess some of their biggest guilty pleasures, or show off their best dance move. “The value is not so much in the question itself, but in the conversation that the question sparks,” says Anna Akbari, PhD, a sociologist and former professor in the department of media, culture and communication at New York University.

No matter what the answer is, you now have the opportunity to ask more questions and uncover deeper layers, she explains. Because, while asking those silly questions might seem insignificant on the surface, they ultimately reveal something about your friends.

“The question and its answer is a starting point for a conversation journey that maybe you wouldn’t be having with that friend,” says Akbari.

So, gather your squad (preferably over a bottomless mimosa brunch), and try injecting a few of the following questions into the conversation to see where it gets you:

1. Who was your first celebrity crush, and are you still crushing on them?

2. What’s your go-to dance move, and can you show me? (Pleeeeease.)

3. If you got to choose your name, what would it be and why?

4. If you could use magic to do one mundane task for the rest of your life, what would it be? (Bonus question: What would you name the spell?)

5. What’s the weirdest item you keep by your bed?

6. What TV show would you want to be in? Which one would you not want to be in? (Not The Handmaid’s Tale, please.)

7. What’s the strangest purchase you’ve made or almost made on Amazon?

8. What is the best excuse for being late you’ve heard or used?

9. Do you have a secret talent? Can you do it right now?

10. When you were a kid, what name did you give your favorite toy or stuffed animal?

Want more reasons to bust a gut with your besties? Check out these hilarious friend fails:

11. If you had a pet parrot, what would you teach it to say?

12. What is one band or musician you would love to party with?

13. What’s the best pick-up line you know?

14. What is your go-to movie when you need a pick-me-up?

15. What is your go-to guilty pleasure song?

16. If you could make the ultimate sandwich, what would be on it?

17. What is the worst fashion decision you’ve ever made? Do you have a picture of it?

18. If you could invent a holiday, what would it be?

19. What book or series did you wish you could live in?

20. If you could be the best in the world at something, what would it be?

21. What is your favorite room in your home?

22. What’s the strangest thing you’ve ever eaten?

23. What item do you think (or tbh, hope) will be obsolete in 20 years?

24. If you could choose a lifetime supply of anything, what would it be?

25. What’s the weirdest thing you wanted to be when you grew up?

26. If you were the ruler of the world, who would be your top adviser?

27. What’s the worst date you’ve been on?

28. If you had to eat the same meal at least once a day, what would it be?

29. What would be the tagline to the sitcom of your life?

30. What’s your most unpopular food opinion?

31. Which piece of clothing do you no longer wear but can’t throw away?

32. Do you like pineapple on pizza? Make the case why or why not.

33. What word do you want added to the dictionary, and what is its definition?

34. What two normal activities would be really weird if you did them back to back?

35. Have you or someone you know seen your doppelgänger?

36. What food do you think would represent each U.S. state?

37. If you opened a store, what would you sell and what would be its name?

38. What’s the funniest thing you’ve read recently?

39. If you were famous, what would your stage name be?

40. What character from a movie/book/show do you relate to the most and why?

41. Who do you think will be playing on “oldies radio” in 30 years?

42. What is a food combination that people eat that you just can’t get behind? (For example: dipping french fries in Frosties.)

43. Where is the coolest place you’ve ever pooped?

44. What is something you do that would be embarrassing if everyone found out?

45. What celebrities would you want to play your parents in a biopic about your life?

46. If you were arrested, what would it be for?

47. What’s the worst (fake) brand name you can think of for items you use every day?

48. Who is the one celebrity you would want to be friends with? Who would you not want to be friends with?

49. What is your favorite line from any movie?

50. Is a hot dog a sandwich?

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