Sign on the side of the road with an arrow and text that reads road trip.

150 Entertaining Questions For A Road Trip To Spark Conversations

Road trips are really all about the journey. Spending that much time in the car with your loved ones gives an amazing opportunity to have some interesting conversations. Pulling out a list of fun, silly, thoughtful questions for a road trip will help make new memories and maybe even bring out a laugh or two.

Throwing random road trip questions back and forth can lead to giggles, curiosity and learning. 

Whether you are hitting the road to a National Park, a camping trip close to home, or a cross country adventure, these Road Trip Questions will make the time pass quicker. While they won’t guarantee no arguments, they are guaranteed to entertain (and distract) when needed.

We’ve reached into the far corners of the internet and our mind to compile our list of the top 150 questions for a road trip, and broken them out into the following categories:

  • Road Trip Questions for Couples 
  • Road Trip Conversation Starters
  • Funny Road Trip Questions
  • Would You Rather Questions for Road Trips
  • Family Road Trip Questions
  • Funny Road Trip Questions for Families
  • Would You Rather – Family Road Trip Questions

There is something here for everyone, so let’s shut the car door on boredom, and get this adventure started.

Road Trip Questions for Couples

Nothing beats starting out on your adventure together as a couple. The open road, the excitement and sites soon to be seen. After a while the buzz does die down and boredom or ennuie can set in. Spark up a conversation once the anticipation has waned a bit.

With miles to go before we sleep, it’s the perfect time to learn more about your sweetie, rather than staring aimlessly out the window at mile markers. Let the journey guide your road trip questions for couples.

  1. How has our relationship changed you?
  2. What do you wish you had more time to spend on?
  3. Where do you see us living in 5 years?
  4. If you won $5 million, what would your first  just-for-fun purchase be?
  5. What was one thing you were afraid to tell me when we first started dating?
  6. How strict were your parents?
  7. If money were no object what would you be doing right now?
  8. What is your perfect couples vacation?
  9. What is the accomplishment you are most proud of in your life?
  10. List your 3 favourite things about me?
  11. What’s one compliment you wish I would give you?
  12. Are you a morning or evening person?
  13. What’s the strangest thing you’ve been asked in an interview?
Happy couple smiling at each other in a car on road trip.
  1. What is your top goal in the next 12 months, and how will you reach it?
  2. What are those little things that make your day brighter?
  3. If you could change one thing about our life now, what would it be and why?
  4. What do you love about yourself?
  5. What’s the one thing I do that annoys you the most?
  6. What are you most afraid of?
  7. What’s the bravest thing you’ve ever done?
  8. What motivates you?
  9. What is a relationship breaker for you?
  10. How would you describe yourself in three words?
  11. Favourite breakfast food?
  12. If our relationship were a movie, what movie would it be?
  13. Are you a pre-travel checklists kinda person or last minute packer for trips?

Road Trip Conversation Starters

Travelling with friends, strangers, a partner or dog, you are bound to run out of things to talk about. Come prepared and avoid the dreaded silence (if that bothers you) with some fun, deep and the occasionally silly ideas.

Kick up your quality time together on the highways and byways and try one of these road trip conversation starters.

  1. As a kid, what did you want to be when you grew up?
  2. What’s the most embarrassing thing you’ve done?
  3. What’s your #1 guilty pleasure?
  4. If you could be a world renowned expert at something, what would it be and why?
  5. Top three favourite musicians?
  6. Which genre of music is your least favourite and why?
  7. If you could be any famous person, from any time, who would you be and why?
  8. If you could build a themed hotel what would the theme be?
  9. Would you rather have a live-in chef or massage therapist?
  10. What’s the worst gift you’ve ever received?
  11. If you could go back to your childhood, what one skill would you learn?
  12. What is your favourite thing about travel?
  13. What is your least favourite thing about travel?
  14. What’s the longest road trip you’ve ever taken?
Empty Road between two rocks. A mountain in the distance.
  1. Who are your 3 favourite people in the whole world and why?
  2. How was your life different one, three, five years ago?
  3. If you could go back in time and change one thing in history, what would it be and why?
  4. What is the creepiest place you’ve ever been?
  5. If you could wake up tomorrow and know how to do anything, what would it be?
  6. What’s your biggest regret?
  7. What are you most proud of?
  8. Has an art piece / exhibit ever moved you, if so why? 
  9. What are you most grateful for?
  10. What is your most memorable experience?
  11. Do aliens exist?

Funny Road Trip Questions 

Inject some humour into the car. When your butt starts to become numb, and you can’t take listening to that Tiffany song about the flowers you gave me (from the 80’s), that your partner in crime insists on listening to for the 5th time, you’ll thank me.

  1. What’s the  longest time you’ve gone without a shower or bath at one time?
  2. Have you ever skinny dipped? If so, where’s the craziest place you’ve done it?
  3. In highschool, what is the most embarrassing thing that happened to you?
  4. If you could give everyone on earth one trait, what would it be?
  5. What’s the worst piece of advice, anyone has given you?
  6. What’s the worst piece of advice you’ve ever given someone else?
  7. What was the best toy of the 80’s / 90’s?
  8. Favourite band / song to play air guitar to as a teenager?
  9. What’s the last text you sent?
  10. Where’s the strangest place you’ve ever slept?
  11. Would you ever apply to a reality tv show?
  12. Which tv show is your guilty pleasure?
  13. Who was your celebrity crush as a teenager? Now?
  14. What actor would play you in a film?
  15. What character would you most like to play in a film and why?
  16. What would you do if the zombie apocalypse happened tomorrow?
  17. What’s your favourite and least favourite word?
  18. What’s a lie you’ve told to get out of work?
  19. If you had an extra body part, what would it be?
Vehicle driving down a mountain road. Text overlay 150 Fun questions for a road trip. Avoid boredom and awkward silences.

“Would You Rather” Questions for a Road Trip

  1. Would you rather live in outer space, or in the ocean deep? 
  2. Would you rather be stranded on a deserted island or in the middle of a desert?
  3. Would you rather never need to sleep, or never need to eat?
  4. Would you rather be loved or feared by all?
  5. Would you rather mountain climb or skydive?
  6. Would you rather be fluent in every language or know how to play any musical instrument?
  7. Would you rather be a movie star or a famous musician?
  8. Would you rather have super strength, or control the elements?
  9. Would you rather find your passion or the love of your life?
  1. Would you rather be able to breathe underwater or fly?
  2. Would you rather take an all-inclusive resort vacation to Jamaica or a backpacking trip to South America?
  3. Would you rather live in a hot climate or a cold climate?
  4. Would you rather live by the ocean or in the mountains?
  5. Would you rather be given physical presents or experiences as gifts?
  6. Would you rather give up your phone or wear crocs for the rest of your life?
  7. Would you rather clog the toilet on the first day of a new job or a first date?
  8. Would you rather be stuck in a closet full of snakes or tarantulas?

Family Road Trip Questions

If you’ve ever taken a long road trip with kids, you understand the need to head off the dreaded “Are we there yet” question every 5 minutes.  Asking fun, silly and thoughtful questions will help keep the masses amused, off their devices, and not fighting. At least for a little while.

While the previous questions could be adapted to suit many age groups, these family road trip questions are fun, and safe for the younger  crowd.

  1. If a genie granted you one wish, what would you wish for?
  2. If you could only eat one thing for the rest of your life, what would it be?
  3. What is your earliest memory as a kid?
  4. How would you describe your family in one word?
  5. Which family tradition is your favourite?
  6. What is your favourite family activity?
  7. What are your top 5 family bucket list items? (Find Bucketlist Ideas Here)
  8. What are three things you are thankful for?
  9. If you could switch places for one day with someone who would it be and why?
  10. Who is the kindest person you know? Why are they kind?
  11. Who is your best friend and why?
  12. What is your perfect family vacation?
  13. If you could have a family pet, what would it be and why?
  14. If you could travel anywhere, where would you go?
  1. Describe yourself in three words.
  2. What is the one thing you can’t live without?
  3. If you opened a store, what would you sell
  4. What does it mean to be happy?
  5. Where do you want to live when you grow up?
  6. What makes you feel loved or special?
  7. Describe your perfect treehouse.
  8. What rule makes no sense to you?
  9. What is something you are good at?
  10. What is one thing you wish you could change about the world?
  11. What is one thing you wish the world, your family or friends knew about you?
  12. What makes a good friend? How are you a good friend to others?
  13. If someone gave you $100 what would you do with it?

Funny Road Trip Questions For Family

Funny road trip questions kids will love to ask and answer. Expect a few giggles, or even a belly laugh as you all think up the answers to these silly questions.

  1. If you could ask your pet any question what would you ask? 
  2. If your pet could talk, what do you think they’d say?
  3. If you could invent a new ice cream flavour, what would it be?
  4. If you could change your name, what  name would you choose?
  5. What’s the most annoying thing your brother / sister / dad / mom has ever done?
  6. What do you do that annoys your brother /  sister / mom / dad etc. the most?
  7. If you could only eat one food for the rest of your life, what would it be?
  8. If you could be a superhero, who would you be and what superpower would you have?
  9. Who would win in a fight between Godzilla and King Kong
  10. Who would win in a fight between a shark and a zombie
  11. If there was a zombie apocalypse which 3 people would you want with you and why?
  12. If you could run away with the circus what type of performer would you be?
  13. If you could create a new holiday, what would it be and how would you celebrate?

Would You Rather – Family Road Trip Questions

If you have younger kids they may find having only two choices easier than open ended questions. These are all clean, kid friendly would you rather questions you can pull out for your next road trip without worries.

  1. Would you rather have a robot servant or a self driving car?
  2. Would you rather camp in a USA National Park or vacation at a resort in Hawaii (Hawaii with Kids)?
  3. Would you rather only be able to eat spaghetti or pizza for the rest of your life?
  4. Would you rather be a mermaid or a dragon?
  5. Would you rather be able to control water or fire?
  6. Would you rather be an expert dancer, or an expert skateboarder?
  7. Would you rather pet a cheetah or a koala bear?
  8. Would you rather be a famous singer or a famous artist?
  9. Would you rather go ride a rollercoaster or a waterslide?
  10. Would you rather go back in time or ahead to the future?
  11. Would you rather get stuck overnight in a toy store or a candy store?
  12. Would you rather eat candy for a week, or not have a bedtime for a week?
  13. Would you rather be able to talk to animals, or speak any language you want?
  14. Would you rather fly a plane or captain a pirate ship?
  15. Would you rather be able to fly or breath underwater?
  16. Would you rather be a detective or a pilot?
  17. Would you rather be the smartest person on the planet or the funniest?
  18. Would you rather brush your teeth with milk or lemon juice?
  19. Would you rather be a scientist or a writer?
  20. Would you rather visit the space station for a week or live in a submarine for a week.
  21. Would you rather eat a bowel of spaghetti noodles without sauce, or a bowl of sauce without noodles?
  22. Would you rather have an elephant sized cat or a cat sized elephant.

Conclusion: Questions For A Road Trip

Well there you have it. Fun, silly, deep, conversation starters to pass the time on your wild road trip adventures with friends and family, or as a couple. I can’t wait to try a few out myself this summer.

Do you have a favourite conversation starter? Let us know in the comments below or connect with us on social media. We’d love to hear from you!

Related road trip destinations and tips:

2 thoughts on “150 Entertaining Questions For A Road Trip To Spark Conversations”

  1. We have a long family road trip
    planned for this summer, so l‘m definitely bookmarking this post. I can‘t wait to hear some of the answers!

  2. These are so great! Thanks for sharing them. I want to plan a family road trip this summer and this will definitely be a great thing to add to the journey and make it a little more fun

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