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48 Road Trip Questions to Ask Your Partner During Long Drives

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Heath and I have been road tripping together for a decade now. That’s a lot of chatting during long drives, traffic stops, and construction zones. Sometimes it feels like we know everything about each other.

Which is when we pull out our fun list of questions to ask each other to keep the drives entertaining. We’ve learned so many things about each other we wouldn’t otherwise know!

Like Heath didn’t know that if I won the lottery, I would charter a yacht to take us and all our favorite people cruising through the rivers in Europe. (But also, does he even KNOW me?! Of course that’s what I would do!)

Feel free to save this list for your next road trip! Just add it to your Google Drive 🙂

This list was inspired by many other lists of questions to ask your friends and partners by people like Justin Mares, Noah Kagan, Ramit Sethi, & fellow RVer, Lindsey Nubern.

Skip around and ask your favorites. Mine are 2, 10, 30, 35, 45, & 48! I also have some very serious thoughts on #31 that no one needs to know.

  1. What is one article of clothing that someone could wear that would make you walk out on a date with them?
  2. If you could have someone on your full-time personal staff, what would you have them do? Personal chef? Masseuse? Maid?
  3. What is your favorite body part on yourself?
  4. What’s the favorite thing you’ve bought this year?
  5. What’s the worst job you’ve ever had?
  6. What’s one bad habit you’re trying to get rid of?
  7. If you can instantly become one overnight, what would you want to be an expert in/at?
  8. What’s something you believe that almost everyone else disagrees with you about?
  9. If you could send a message to the entire world, what would you say in 30 seconds or less?
  10. If you had to teach a class on one thing, what would you teach?
  11. What’s the best piece of advice you’ve ever been given?
  12. When you die, what do you want to be remembered for?
  13. Someone gets a text message from you, and they’re not sure it’s you. They’re worried someone stole your phone. What could they ask to make sure it’s actually you?
  14. When you think about success, who comes to mind and why?
  15. What are your showers like?
  16. What is something you like that most people don’t?
  17. What’s left on your bucket list? What on that list do you know you’ll never accomplish? How does that make you feel? 
  18. What’s your recurring nightmare?
  19. What was your first screen name?
  20. Last time you ate at McDonald’s?
  21. Have you ever been scammed?
  22. If you started over at 18 knowing everything you know now, what would you do differently?
  23. When were your parents most disappointed in you?
  24. If you could have someone full-time remind you of something every day, what would you want to hear?
  25. Which band/artist – dead or alive – would you want to play at your funeral?
  26. What was the first book you read that changed your mind?
  27. Who’d play you in a movie?
  28. Which nicknames have you been called?
  29. What book do you recommend to everyone? 
  30. You must go on a road trip from Bar Harbor, Maine to San Diego, California. You have to bring 3 people. Who are they? Which route are you taking, and what will you see along the way?
  31. If there was a sandwich named after you, what would be on it?
  32. What’s your best scar story?
  33. If you had to delete all the apps on your phone and keep only three, which ones would you keep?
  34. What are you most excited about right now?
  35. You have 1 day to spend 1 million dollars, how do you do it?
  36. What about yourself are you really self-conscious about?
  37. What are 3 adjectives to describe each of your parents?
  38. You have $100k. You have to donate or create a charity, what cause would you support?
  39. What are you really good at?
  40. Buried or cremated?
  41. What would be your best day ever?
  42. What day would you want to repeat forever?
  43. What’s a compliment someone gave you still think about?
  44. What is your favorite thing to spend money on? What’s something you spend money on and never feel guilty about it? 
  45. What’s something you don’t spend money on right now that you want to spend money on in the future? (i.e. name brand clothes, nice restaurants, first-class travel, etc.)
  46. What activity could we do that you would say is “living your best life”? 
  47. The lottery is at $$$ this week. If we won, how would you spend your money? You have to spend every cent! 
  48. Where to next? 

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