50 Road Trip Questions for Couples

Our last big trip was to Ireland in January 2018. Greece in 2020 got postponed and I'm hoping to get there in April 2021. For now, in the uncertain times of COVID, travel is mainly taking place by car, if at all.  We road tripped it to my home state of Pennsylvania at the end of June and have another (mini) road trip coming up at the end of the month!

Road trips with your sweetheart can offer you a lot of time to connect, but can also get long and boring. Having some conversation starters in your back pocket is never a bad idea!

//1// What is your favorite way to relax when things are hectic?
//2// What do you wish you could spend more of your time doing?
//3// What destination do you want to visit together next?
//4// If you could go back in time to before you were born, what period of history would you choose?
//5// Which of your childhood vacations would you like to recreate for our kids?
//6// If we had to live in one of the places you've visited on vacation which one would be your first choice?
//7// What activities zap your energy the most?
//8// What made you decide to ask me out on our first date?
//9// What overseas location would you most like for us to visit together?
//10// What talent do you really wish you had?
//11// What would be your ideal getaway for a long weekend?
//12// If your boss said he/she would donate $10,000 to a charity of your choice which one would you pick?
//13// What made you accept when I asked you out on our first date?
//14// In what way are you most like one of your parents?
//15// What is your least favorite place you've visited on a trip?
//16// What is the strangest food you have ever eaten?
//17// Who is the most famous individual you have met in person?
//18// What are the first two adjectives that come to mind when you think about our relationship?
//19// Which one of your friends would help you dispose of a body if you needed them to?
//20// If you could only eat one food for the rest of your life what would you choose?
//21// What would we do on your ideal date night?
//22// What irritates you the most in restaurants?
//23// What is the biggest adventure we've had together so far?
//24// What comedy TV show best describes our life?
//25// What song do you really love to listen to when you are on a long drive?
//26// Which public figure do you admire most?
//27// What qualities or characteristics in a person would cause you to want to have nothing to do with him/her?
//28// What do you like least about travel?
//29// What is your all-time favorite memory of our time together?
//30// What an event or activity you have attended with me that you would have preferred not to participate in?
//31// Other than a dog or cat what kind of pet would you most like us to have?
//32// What book has had the most impact on your life?
//33// What was the first thing you purchased using money you earned?
//34// What two words would you use to describe my values?
//35// What's your favorite thing for us to do together on weekend when the weather is too bad to go out?
//36//What is the first thing you noticed in a man/woman?
//37// What have you never done before that you would like for us to try together if money and time were no object?
//38// What negative thing has happened to you that actually turned out for be for the best?
//39// What theme park would you like us to visit together?
//40// If there was a movie made about us who would place me and you?
//41// What is the most courageous thing you have done so far?
//42// If you inherited $10 million what would you buy first (after all the bills/debts were paid)?
//43// What is one thing you wish you could change about the early days of our relationship?
//44// What compliment would you like to hear from me?
//45// In what ways has our relationship changed you?
//46// What is something you did not want to do at all that turned out to be a terrific experience?
//47// What would be your idea of a perfect 25th anniversary trip?
//48// What irritates you the most in restaurants?
//49// What ideas do you have about how we could improve the 'couple time' we spend together?
//50// What food would you never eat under any circumstances?