101 Fun and Random Road Trip Questions To Uncover Your Friend’s Secrets

Post Summary: 101+ Fun Road Trip Questions (With Free Download!)

Ahh, west coast road trips. The great American tradition that has withstood the test of time.

Berty and I like to believe that some of our favorite conversations happen in the car, both with each other and with our friends.

We have always been a fan of road trip questions because they allow us to inquire about things we wouldn’t normally ask each other.

Whether you’re going across the country, or just to the hiking trail nearby, it’s the people you go with that make the journey worthwhile.

However, we’ve always been on the search for the perfect road trip questions list! We needed one with a good mix of funny and serious questions, as well as simple and thought-provoking ones

So we thought we’d make our own road trip questions list!

We scoured the internet for some of our favorite road trip questions and compiled them together in this list.

We’ve included our favorite and fun travel questions and made up our own along the way. You surely won’t be bored on your next trip! Enjoy!

101 Fun And Random Road Trip Questions To Ask Your Friends

1. What is your favorite kind of doughnut?

2. On a scale of 1-10, how strict are/were your parents?

3. If you could take a month-long road trip, what would be your route? (Need suggestions? Try the PNW or Utah)

4. Who are the 3 greatest living musicians?

5. What was your worst date? Tell a play by play.

6. How do you like your coffee in the morning?

7. What accomplishment are you most proud of?

8. What is the first thing you do when you get out of bed?

9. Which of your friends are you proudest of? Why?

10. Have you ever been skinny dipping?

11. What’s the most beautiful place you’ve ever been?

12. What are your 3 favorite movies?

13. Tell me 3 things you remember about kindergarten.

14. If you could live in any TV home, what would it be?

15. What was the first CD you ever owned?

16. If you could ask your pet 3 questions, what would they be?

17. If you had to live in a different state, what would it be?

18. Using one word, how would you describe your family?

19. What is the scariest movie you’ve ever seen?

20. How often do you go to the gym?

21. What is the wildest thing you would consider doing to your hair?

22. If you could travel anywhere in the world, where would it be? (Discover our clickable destination maps here)

23. What is your favorite family tradition?

24. What’s the first thing you do when you get home from a trip?

25. Would you rather spend five days exploring Disney or New York City?

26. If we had to live in one of the places you’ve visited on vacation which one would be your first choice?

27. What do you like the least about travel? (Read about how we fight when traveling)

28. What is your favorite part of travel?

29. What is the one thing that would be a relationship breaker for you?

30. What is your goal for the next 12 months? How do you plan to reach it?

31. Have you ever achieved a New Year’s resolution?

32. What is your favorite kind of cereal?

33. Are you usually early or late?

34. What one thing annoys you most at a restaurant?

35. What household chore have you never done?

36. What language would you like to master?

37. Who would you love to punch in the face?

38. What is your favorite event in the Winter Olympics?

39. What was the best book or series that you’ve ever read? (OR, your current favorite podcasts for a road trip?)

40. Where is the farthest place you’ve ever traveled in a car?

41. Share your top 5 favorite bands/artists.

42. Who is your most admired athlete of all-time?

43. What do you think will the be “throwback” style of the 00s?

44. What do you like most about your family?

45. What is your least favorite holiday and why? Most favorite?

46. What are some small things that make your day better?

47. If you owned a professional sports team, what team would you own?

48. What is the MUST SEE movie out right now?

49. What shampoo and conditioner do you use?

50. What are three key elements in every successful relationship?

51. If you didn’t have to sleep, what would you do with the extra time?

52. What hobby would you get into if time and money weren’t an issue?

53. Describe your dream home – where would it be and what would it look like? (Would it look like this PNW Cabin?)

54. Do you prefer early mornings or late nights?

55. How do you like to cook your eggs?

56. What shows are you currently into?

57. Which exotic animal would you want as your pet?

58. What is something that is considered a luxury, but you don’t think you could live without?

59. Would you rather go bungee jumping or skydiving?

60. How different was your life one year ago?

61. What kind of art do you enjoy most?

62. What’s the best way a person can spend their time?

63. Where is the most relaxing place you’ve ever been?

64. Who is your favorite influencer?

65. If you had to give up every social media platform but one, which one would you keep? (By the way, we’re on Instagram here)

66. What is one skill you really want to master?

67. What is the most embarrassing thing that happened to you in high school?

68. What is something you will NEVER do again?

69. Where is the creepiest place you have ever been?

70. How long have you gone without taking a bath/shower?

71. What band would you consider your guilty pleasure?

72. Would you rather explore space or the deepest part of the ocean?

73. What has been the best museum you’ve visited? (Our favorite is in this post, psst, it’s hosts the Mona Lisa!)

74. Would you rather climb a mountain or deep sea dive?

75. What’s the most illegal thing you’ve done?

76. What’s the best and worst piece of TRAVEL advice you’ve ever received?

77. When do you feel truly “alive”? (Hiking this trail in Zion was pretty exhilarating…)

78. What is your biggest kitchen fail?

79. What are you really good at, but kind of embarrassed that you are good at it?

80. Which of your scars has the best story behind it?

81. What do you regret not doing or starting when you were younger?

82. What was the best toy of the 90s?

83. What is your spirit animal?

84. If you had to wear one brand of clothing for the rest of your life, what would you choose?

85. What does the last text message on your phone say?

86. Which movie made you cry? Why?

87. Who is your celebrity crush?

88. What is your favorite TV series?

89. How many pairs of shoes do you own?

90. What has been your most expensive Uber ride?

91. What is your favorite location to go camping? (Ours is here, on this awesome Washington beach!)

92. Have you ever had to go to the hospital?

93. Would you ever consider applying for The Bachelor/Bachelorette?

94. How many pillows do you sleep with?

95. Do you prefer warm weather or cold weather?

96. What is your favorite breakfast diner order?

97. Do you have an irrational fear?

98. What is your go-to dance move?

99. Where do you do most of your online shopping?

100. Do you read the newspaper?

101. What has been your favorite photo you’ve taken?


These car ride questions are only on the blog! Let’s say this is your reward for making it all the way to the bottom of the post. It takes a lot of dedication to read that long, and we love you for that! Keep reading for more questions to ask on a road trip…

102: What’s the weirdest place you’ve ever slept?

103: What was the first national park you ever visited? If not, which one is on the top of your list to explore?

104: Did you go camping in your childhood? Where?

105: What school project were you most proud of?

106: How would you describe your decor style?

107: Do you have a favorite flower?

108: Have you ever tried essential oils? Why or why not?

109: If you could paint your house any color, which one would you choose?

110: Did you get through every single one of these road trip questions? If so, we seriously admire your dedication!!

Do you like these road trip questions? Let us know if you want to see a new list with even more ways to entertain you on a road trip!


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Umpqua National Park, Toketee Falls, Oregon TheMandagies.com

Make sure to follow our Road Trip board on Pinterest for more road trip question inspiration!

Do You Have Any Road Trip Questions You’d Like To Ask Someone? What Are Some Other Games You Like To Play While On A Road Trip? Tell Us In The Comments Below!