160 FUN, DEEP, AND SOMETIMES SILLY ROAD TRIP QUESTIONS

empty street on winding road

Post Summary: Epic list of fun road trip questions and would you rather prompts so you never get bored on the open road. The list includes road trip questions for couples and adults and road trip questions for family.

When deciding to go on a road trip, the journey is truly as great as the destination. It’s in those long car rides that the best conversations can happen. We spent a year road tripping across America with our wild toddler in tow, so we like to believe we’ve earned our road trip badge of honor. Top on our list of favorite road trip games to do is a back and forth of random road trip questions.

We’ve compiled a list of 160 open-ended questions for a road trip that is guaranteed to be a conversation starter. This list is inspired by our own long road trips and meant to be inciteful, entertaining, and a great way to connect to whomever you’re traveling with.

The first list consists of road trip questions geared toward adults and the second list is questions geared towards children and families. As you go through the car ride questions, we encourage you to allow room for flexibility and storytelling. Allow the questions we’ve provided to inspire your own questions. Perhaps you even make a game of it and try to guess what the other person’s going to say. Regardless, have fun, and stay curious about your travel partner!

More Road Trip Posts:
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15 Helpful Tips For Roadtripping With A Toddler
17 Western National Parks To Visit This Year
The Must-See National Parks On The East Coast

Road trip van on sidewalk

103 Fun Questions For A Road Trip

1. What did you want to be when you were a kid?

2. What was the best meal of your life?

3. What was an embarrassing moment you had in childhood?

4. What three things would you bring from your house in the event of a zombie apocalypse? 

5. If you could be the leading expert in something, what would it be?

6. Who are the top 3 people who have influenced your life?

7. What’s a guilty pleasure of yours?

8. What element do you feel most connected to – earth, air, fire, water – and why?

9. What is one talent or skill that you wish you had?

10. What’s your funniest drunk memory?

11. Who’s the most famous person you’ve ever met?

12. Which instrument speaks to your soul the most?

13. What song could you listen to over and over and not get tired of?

14. What three things would you buy if you won the lottery?

15. What would you like to change about yourself?

16. What do you love about yourself?

17. What’s your favorite thing about me?

18. What’s your favorite place in the world?

19. What’s your most magical childhood memory?

20. What one piece of advice would you give your younger self?

21. What is your definition of a soul?

22. What three words would you use to describe me?

23. What is your primary love language? (gift-giving, quality time, acts of service, physical touch, words of affirmation)

24. What items are on your bucket list?

25. How many bones have you broken?

26. What are you most proud of doing?

27. If you could live anywhere in the world, where would you live?

28. If you could be more disciplined and wake up early, what would you add to you morning routine?

29. If you could switch places for a week with anyone in the world, who would you switch with?

30. If you could have a conversation with one non-living person, who would you talk to?

31. What time period would you like to take a time machine to and observe for yourself?

32. What was your first record/tape/cd/mp3?

33. Have you ever gone skinny dipping?

34. If you could communicate with one animal species, what type of animal would it be?

35. What two languages would you like to speak?

36. What are your three favorite movies?

37. What are two things a love relationship needs to thrive?

38. What is one thing you would love to take out of your daily routine?

39. If money weren’t an issue, what is the one thing you would love to do?

40. What does your dream home look like and where is it?

41. When have you felt most at peace in your life?

42. What piece of art has profoundly impacted or moved you?

43. Have you ever broken the law?

44. What would your perfect date be like?

45. Who would you love to have an all out verbal smackdown with?

46. Which celebrity would you choose as your “okay to cheat on” person?

47. If you could be invisible for one day, what would you do?

48. How have you changed in the last 5 years?

49. What do you wish your parents had done differently with you?

50. Can money bring happiness?

51. What scandalous thing would you do if you could get away with it?

52. What has been your favorite travel experience?

53. What is a hero and who is a hero to you?

54. When have you exhibited bravery?

55. Are you more like your mom or dad and how?

56. Would you describe yourself as impulsive?

57. If you had $100,000 to help people with, what would you do?

58. What animal would you like to come back as?

59. What kind of superhero would you be and what’s your superhero power?

60. When have you felt the most gratitude in your life?

61. What do you think has been one of the most impactful inventions?

62. What sound do you love?

63. How would you like to be remembered?

64. What’s your favorite horror film?

65. What food could you eat every day for the rest of your life and never get tired of?

66. If you could magically imbue one personality trait into every single human on earth, what would it be?

67. Do you think people have the ability to change or are we fundamentally the same all our life?

68. When is the last time you apologized for something you did?

69. Are you proud of what you are doing with your time right now?

70. What motivates you to work hard?

71. What is the best gift you have been given?

72. If you could reconnect to one friend that you’ve lost touch with, who would it be?

73. If you had to spend a week with no internet, what would you do?

74. What are two pet peeves of yours?

75. When was the last time you felt complete and total bliss?

76. What was your most prized possession as a child?

77. What do you fear about getting older?

78. What do you regret not doing when you were younger?

79. If you could live anywhere for a year, where would it be?

80. Who are your top three favorite singers/bands/musicians of all time?

81. If you could go back in time to change one thing, what would it be?

82. Who would be your five (alive or living) guests at your dinner party?

83. What deceased musician or singer would you love to see in concert?

84. What would you do if you could spend one day as the other gender?

*Lastly, we’ll be ending the road trip questions with a fun round of would you rather.

85. Would you rather have picture-perfect health until you die or always have 20 million dollars in the bank till you die?

86. Would you rather have super strength or the ability to move items with your mind?

87. Would you rather go on safari in Africa or a cruise to the Galapagos Islands?

88. Would you rather live in the mountains or on the water?

89. Would you rather eat only cold soup for the rest of your life or never have sex again?

90. Would you rather dive with sharks or swim with orca whales?

91. Would you rather live somewhere scorching hot or freezing cold?

92. Would you rather have the ability to play every instrument or know every language?

93. Would  you rather live without music or without television?

94. Would you rather be able to freeze time or go back in time?

95. Would you rather be able to breathe underwater or fly?

96. Would you rather never drive again or never fly again?

97. Would you rather never see again or never speak again?

98. Would you rather adopt a baby wolf or baby koala?

99. Would you rather have a conversation with Jesus or Buddha?

100. Would you rather talk to Mary Magdalene or Mother Mary?

101. Would you rather be a genius in astrophysics or neuroscience?

102. Would you rather be a savant at painting or a prodigy of music?

103. Would you rather take a weekend to road trip to different natural hot springs or take a foodie weekend to gorge on amazing farm to table food?

Boy on road trip standing up through the car of a sun roof pointing at a mountain.
Photo from Kelly Sikkema

57 Road Trip Questions For Family

While many of the above questions could be used for families, these questions are specifically tailored for families with young kids. It doesn’t mean adults can’t enjoy them too! The heart of the questions are meant to inspire conversation, laughter, and to potentially learn something new about your child. We encourage you to ask why to whatever they answer and most of all, to enjoy your time together.

1. Who is your favorite superhero and why?

2. Who is the funniest person you know?

3. If you were the parent for a day, what would you do?

4. If you could be an animal for one day, what would you be?

5. If you could communicate with one animal species, what would it be?

6. What three words would you use to describe yourself?

7. What would the perfect day be for you?

8. If you could change your name, what would you change it to?

9. What do you think makes someone a hero/heroine?

10. In a fight between an alien and a robot, who would win?

11. What school subject do you wish you could be better at?

12. How would you design the perfect treehouse?

13. How do you show people you love them?

14. If you could give 200 dollars to help someone, what would you do?

15. What makes you feel special?

16. How do you think animals talk to each other?

17. What’s your favorite sound?

18. If you could be a circus performer, what kind would you want to be?

19. What’s your favorite season – winter, spring, summer or fall?

20. If you could change one thing about the world, what would it be?

21. If you could visit anywhere in the world, where would it be?

22. If you could be anyone for a week, who would you be?

23. What are you grateful for today?

24. What are the traits of a good friend?

25. What rule do you think makes no sense?

26. If you were invisible for a day, what would you do?

27. If you could give one piece of advice to the world, what would it be?

28. If you could live somewhere else for a year, where would it be?

29. What five things would you take with you onto a deserted island?

30. What’s something you’re really good at?

31. What’s something you wish you could be better at?

32. If you found a genie, what would your three wishes be?

33. If you could go back in time, where would you travel to?

34. What’s your favorite thing to do outside?

35. What does happiness feel like?

36. What animal would you like to have as a pet?

*”Would you rather” questions are great options for pre-school aged kids who will enjoy the simplicity of two choices.

37. Would you rather be a magician or a superhero?

38. Would you rather ride a dolphin or a unicorn?

39. Would you rather visit Hawaii or Antarctica?

40. Would you rather see a mermaid or a dragon?

41. Would you rather have your own personal robot or a magic carpet?

42. Would you rather pet a lion or a monkey?

43. Would you rather eat pizza for a week or stay up late for a week?

44. Would you rather fly a jet or captain a yacht?

45. Would you rather be a world-renowned artist or award-winning scientist?

46. Would you rather explore outer space or the bottom of the ocean?

47. Would you rather be an amazing guitar player or drum player?

48. Would you rather have a pet raccoon or pet turtle?

49. Would you rather go to a theme park or a water park?

50. Would you rather climb Mount Everest or swim the Great Barrier Reef?

51. Would you rather go back in time or go into the future?

52. Would you rather get stuck and have to spend the night in a toy store or a candy store?

Our final five family road trip questions aren’t questions that are meant to be answered “correctly.” Instead, they are five simple questions that can be answered in the most inventive and wacky way. It’s to promote creative thinking and to have fun with each other. You can come up with an elaborate story or give a simple one-sentence answer. Encourage your kids to not think about it too much and to say the first thing that comes up. The point is to have fun with each other!

Looking for some family inspiration? Read our post on 40 travel quotes to inspire your next family vacation.

53. Why is the sky blue?

54. Why is lightning loud?

55. Why do rabbits have such big ears?

56. Why do trees grow straight up?

57. Why are strawberries sweet?

We hope you enjoy our list of fun and sometimes random road trip questions. Let us know if you used them and if they inspired some great laughs or revelations. Happy road tripping!

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2 comments
  1. I love these! I always dread the boredom that can come with long car rides. I’m looking forward to playing with these questions on my next trip.

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