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Heath and I have been road tripping together for over 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!)
This list was inspired by many other lists of creative questions 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.
- What is one article of clothing that someone could wear that would make you walk out on a date with them?
- If you could have someone on your full-time personal staff, what would you have them do? Personal chef? Masseuse? Maid?
- What is your favorite body part on yourself?
- What’s the favorite thing you’ve bought this year?
- What’s the worst job you’ve ever had?
- What’s one bad habit you’re trying to get rid of?
- If you can instantly become an expert overnight, what would you want to be an expert in/at?
- What’s something you believe that almost everyone else disagrees with you about?
- If you could send a message to the entire world, what would you say (in 30 seconds or less)?
- If you had to teach a class on one thing, what would you teach?
- What’s the best piece of advice you’ve ever been given?
- When you die, what do you want to be remembered for?
- 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?
- When you think about success, who comes to mind and why?
- What are your showers like?
- What is something you like that most people don’t?
- What’s left on your bucket list? What on that list do you know you’ll never accomplish? How does that make you feel?
- What’s your recurring nightmare?
- What was your first screen name?
- Last time you ate at McDonald’s?
- Have you ever been scammed?
- If you started over at 18 knowing everything you know now, what would you do differently?
- When were your parents most disappointed in you?
- If you could have someone full-time remind you of something every day, what would you want to hear?
- Which band/artist – dead or alive – would you want to play at your funeral?
- What was the first book you read that changed your mind?
- Who’d play you in a movie?
- Which nicknames have you been called?
- What book do you recommend to everyone?
- 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?
- If there were a sandwich named after you, what would be on it?
- What’s your best scar story?
- If you had to delete all the apps on your phone and keep only three, which ones would you keep?
- What are you most excited about right now?
- If you have one day to spend one million dollars, how do you do it? You have to spend every cent in order to keep it!
- What about yourself are you self-conscious about?
- What are three adjectives to describe each of your parents?
- You have $100k and have to donate it or create a charity, which cause would you support?
- What are you good at that you think is underappreciated?
- Buried or cremated?
- What would be your best day ever?
- What is something that always reminds you of me, even when I’m not around?
- What’s a compliment someone gave you that you still think about?
- What is your favorite thing to spend money on? What’s something you spend money on and never feel guilty about it?
- 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.)
- What activity could we do that you would say is “living your best life”?
- The lottery is at $$$ this week. If we won, how would you spend your money?
- What is your favorite family vacation from childhood that you would want to recreate as an adult?
- If this next year were a “gap year” and money were no object, how would you want us to spend it?
- What is the best gift you’ve ever been given?
- What’s something non-work related that you’ve been learning recently?
- What is one moment from the past week that made you truly happy?
- If we got to relive one year of our relationship again, which year would you choose?
- What’s a small gesture I’ve made recently that made you feel loved?
- Where to next?
Feel free to save this list for your next road trip! Just add it to your Google Drive 🙂
