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Funny Questions to Start a Conversation

Break out these 51 questions around the camp fire, on the road, or in the rental house to get your crew united and laughing uncontrollably on your next adventure. This post can also be found in our smartphone app, Trip Pilot, and downloaded to a personal library that works offline.


1. What’s the scariest experience you’ve had in the Outdoors?

2. What outdoor activity are you not currently doing that you would like to learn, regardless of cost?

3. What is your most embarrassing moment while on an adventure?

4. Who is your celebrity crush of the opposite sex?

5. Who is your celebrity crush of the same sex?

6. Would you rather be too hot or too cold?

7. What’s the biggest and most random coincidence you have experienced?

8. What’s your favorite band of all time?

9. What’s your favorite book of all time?

10. If you could have dinner with anyone from history who would it be and why?

11. Have you kissed more or less than 20 people (not including relatives and family)?

12. If you could be any animal what would it be?

13. If you could bring back or keep any fashion trend in history what is it and why?

14. Uphill or downhill, which is better?

15. What is your favorite invention or technology that was created in your lifetime?

16. Beer, Whiskey, Wine, or Tequila?

17. What is your favorite saying?

18. What is your (as you see it) worst guilty pleasure?

19. If you had to only eat one cultures food for the rest of your life, which one would you choose?

20. What is your favorite form of exercise, and why?

21. If you had to sacrifice one body part what would it be?

22. If you could only save one person from certain death, your best friend or Martin Luther King Jr. who would you save.

23. Who is your favorite superhero?

24. If you could take one animated character and turn them real and go on a date who would it be?

25. What’s your favorite movie of all time?

26. What’s something that everybody loves but you secretly hate?

27. Have you ever run away from home? If yes, please explain.

28. What’s the worst trouble you were ever in as a child, and what happened?

29. What’s the funniest thing you could say to a stranger? Include where it happens if it improves the scene.

30. What’s the worst thing to do while drunk?

31. What’s the most embarrassing thing that you have done on a date?

32. What movie scarred you the most growing up?

33. If your boy friend/girlfriend wife, husband, had this name you may not be able to be together.

34. If you had to replace one body part with something else, which body part, and what do you replace it with?

35. Is there anything that you could drop down the hole of an outhouse that would cause you to go in after it? What?

36. What’s the worst place you ever pooped your pants? Do tell.

37. Show the group your go-to dance move.

38. If you were in hell having dinner, who would you be with, what would you be eating, and what is the background music.

39. Make your best farting noise.

40. If for the rest of the trip you could pick one nickname for everyone to call you what would it be?

41. What would be the most annoying animal if it could talk? Do an impresson.

42. What’s the worst pickup line you can think of.

43. What’s one thing you could say on a first date that would make it go horribly wrong?

44. What’s the worst, or most embarrassing thing/style you have worn in the name of fashion?

45. Have you ever seen a ghost, alien, supernatural event that you can’t explain? Please share.

46. What’s something that everyone looks ridiculous doing?

47. What’s the worst buy one get one free deal you can think of?

48. If your friends found out you were arrested what would they assume you had done?

49. What a show or movie do you not wish to admit that you like?

50. What song gets stuck in your head the easiest? Sing it for the group.

51. What’s on the top of your outdoor bucket list?




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