160 Road Trip Questions to Ask in Every Category

November 26, 2020

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Road trips have always held a certain appeal to them. In our distracted and busy world, road trips provide an opportunity away from everyday distractions. Time spent on the road is prime for quality time and long conversations.

My fiancé and I road tripped with another couple last summer when they moved from New York to Oregon. We traveled through thirteen states and spent 48 hours in the car. I anticipated audiobooks, podcasts, and blaring music. To my delight, we spent the majority of the time talking.

Armed with fun and thought-provoking road trip questions to ask, you’d be surprised by how fast the time goes. Where better to practice vulnerability and bring greater meaning into your relationships? And how better to do it than with questions?

There are many great lists of road trip questions out there, but I wanted to make one a bit more organized. Whether you’re looking for serious contemplation or fun banter, nostalgia or forward-thinking, this list of road trip questions will have just about everything you might want.

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Road Trip Questions for Everyone

• Road Trip Questions to Ask About Childhood
• Road Trip Questions to Ask About Goals
• Road Trip Questions to Ask About Adventure
• Road Trip Questions to Ask About Interests
• Road Trip Questions to Ask About Growth
• Road Trip Questions to Ask About Challenge
• Road Trip Questions to Ask About Random Things

Road Trip Questions for Couples

• Road Trip Questions for Couples About Love
• Road Trip Questions for Couples About Commitment
• Road Trip Questions for Couples About Family
• Road Trip Questions for Couples About Conflict

Road Trip Questions for Family

• Road Trip Questions for Family About Love
• Road Trip Questions for Family About Interests and Adventure
• Road Trip Questions for Family About Personality

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Road Trip Questions for Everyone

Road Trip Questions to Ask About Childhood

1. What is something that happened in your childhood that still bothers you?
2. What hopes and dreams did you have as a child that you have given up on?
3. What primary coping strategy did you develop as a child that you still use today?
4. What messages did you receive about what you needed to do to receive love?
5. How did your upbringing shape your view of what you wanted for a healthy family? A relationship?
6. What lesson from childhood has stuck with you the most?
7. Who had the biggest influence on you as a child?
8. What communication patterns did you develop as a child? Are they effective or ineffective?
9. What did you not like about your childhood that you want to change for your adult life?
10. What did you feel most ashamed of as a child? How might this shame still be affecting you now?

Road Trip Questions to Ask About Goals

1. What goals do you have for the next 5 years? 10 years?
2. What goals do you want to achieve before you die?
3. What goals have you given up on? What made you give them up?
4. What makes something worth pursuing in life?
5. What do you need from others when you’re striving for a goal?
6. How does a fear of failure affect you?
7. What dreams are most important to you?
8. What is your process when working toward a goal?
9. What goals do you have for your love life?
10. What goals do you have for your work?

Road Trip Questions to Ask About Adventure

1. What items are on your bucket list?
2. What items have you crossed off already on your bucket list?
3. What have been your most memorable experiences?
4. What does an adventurous life look like for you?
5. What makes you afraid or avoid new adventures?
6. How much do you side on stability and security versus adventure and spontaneity?
7. What’s the last thing you can remember doing that was only about having fun?
8. How often do you prioritize fun in your life?
9. If money wasn’t a worry, what adventures would you go on?
10. How can you bring more adventure into your day-to-day life?

Road Trip Questions to Ask About Interests

1. What do you do for fun?
2. What are your hobbies?
3. What is something that you’re really passionate about?
4. What is something you could spend hours doing?
5. What is something you wish you did more often?
6. If you had to watch a documentary, what would you want it to be about?
7. What do you always have on in the background?
8. How do you feel about travel?
9. What is a guilty pleasure you enjoy?
10. How have your interests changed over the years?

Road Trip Questions to Ask About Growth

1. How are you a different person now than you were five years ago? Ten?
2. What are you most afraid of?
3. What do you have trouble trusting about yourself?
4. How often do your emotions interfere with what you want for yourself?
5. Where in your life do you feel like you’re not living up to your full potential?
6. What are you most grateful for in your life?
7. If you evaluate the narrative you create for your life, is it more negative or positive?
8. If you could go back and change something you said, what would it be?
9. What causes you to feel the most out of control?
10. How often do you feel lost or purposeless? What causes these moments?

Road Trip Questions to Ask About Challenge

1. When have you failed in life?
2. How have you handled each failure in your life?
3. How was failure treated in your upbringing?
4. When in your life have you repeated the same mistakes over and over again?
5. What is one of your biggest regrets? What did you learn from it?
6. What challenges in your life have defined you the most?
7. What is your attitude when facing a challenge?
8. How comfortable are you asking for help when you’re faced with a challenge?
9. What is my most harmful pattern when faced with stress?
10. When do you actively seek out challenges? When do you avoid them?

Road Trip Questions to Ask About Random Things

1. If you wrote a memoir about your life, what would it be called?
2. What fictional world would you want to travel to for a day?
3. What room in your house most represents who you are as a person?
4. How clean a person are you?
5. What is a pet peeve that you have?
6. What behavior do you do that is most likely a pet peeve to others?
7. What phrase or word do you overuse when you talk?
8. If you could only eat at one restaurant for the rest of your life, what would it be?
9. What is something about your personality that you like? Don’t like?
10. What would your friends be surprised to learn about you?
11. What are your favorite movies? What makes them so good?
12. When is the last time you laughed really hard?
13. What was your most memorable moments in school?
14. If you had to go back to school, what would you want to learn about?
15. If you could become a professional athlete in any sport, what sport would you choose?
16. What made you get into your line of work?
17. What makes you get out of bed in the morning?
18. What is one of your strengths?
19. What is something you’re really proud of in your life?
20. How comfortable are you sharing what you believe in?
21. What is something that makes you most angry?
22. What in life makes you feel most excited?
23. How often are you creative?
24. If you could gift everyone in the world one quality, what would it be?
25. What was an embarrassing moment you experienced?
26. What is the most ridiculous thing you’ve ever purchased?
27. What’s the most adventurous thing that you’ve done?
28. What is something you did when you were younger that makes you cringe to think about?
29. How has your fashion sense changed over the years?
30. What are the most meaningful relationships in your life?

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Road Trip Questions for Couples

Road Trip Questions for Couples About Love

1. What does love look like in your mind?
2. How has your perception of love changed during your life?
3. Who is a good model of love in your life?
4. How many times have you been in love?
5. What are the things you love about me?
6. When has your love for someone been tested?
7. How do you express your love?
8. How do you like to receive love?
9. Who do you love in your life?
10. How often do you say, “I love you”?

Road Trip Questions for Couples About Commitment

1. When was the last time you didn’t trust me, and what could I have done differently?
2. What can I do to prove that I am committed to you and our relationship?
3. What are the differences between our definitions of trust and commitment, and how can we resolve them?
4. What healthy relationships do you think are good models of commitment?
5. When have you felt like our commitment has been tested? How did you feel about what happened?
6. How difficult is it for you to trust me?
7. When have you been betrayed by someone you trusted? How did it shape your view?
8. What are your needs from a partner?
9. What little actions have I done that helped promote trust?
10. What does commitment look like to you long-term?

Road Trip Questions for Couples About Family

1. How do you define family?
2. What is your idea of the perfect family? Does it include children?
3. How many children do you want to have?
4. What sort of problems might you encounter while raising children?
5. How can you prevent or tackle these problems?
6. What traditions from your family do you want to preserve?
7. What habits from your family do you want to not repeat?
8. How important is family to you?
9. What do you need to maintain a healthy balance of family and self?
10. What would you consider doing for a family name?

Road Trip Questions for Couples About Conflict

1. What are the significant differences between us?
2. How might these differences cause conflict? What compromises are possible?
3. How did your family handle conflict?
4. What are your most common defensive mechanisms when conflict arises?
5. What are your strengths when dealing with conflicts?
6. What do you consider to be a healthy amount of conflict?
7. What do you consider to be an acceptable argument?
8. What is important for you to not have happen during a conflict?
9. How have we as a couple handled conflict in the past?
10. How can we handle conflict more productively going forward?

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Road Trip Questions for Family

Road Trip Questions for Family About Love

1. What is your definition of love?
2. When do you feel most loved?
3. How do you should people that you love them?
4. How do people show their love differently?
5. Who is somebody who you think needs more love?
6. Why do you think people have trouble feeling love?
7. What does a loving family look like to you?
8. When do you not feel very loved?
9. If you could give everyone in the world one thing, what would it be?
10. Who are the people in your life that are most important to you?

Road Trip Questions for Family About Interests and Adventure

1. What adventures do you want to go on?
2. What do you enjoy doing?
3. What do you notice in common about the things you enjoy doing?
4. How often do you use your imagination?
5. How can you use your imagination more?
6. What are some different hobbies that other people like but you don’t?
7. When is the last time you tried something new?
8. When are you afraid to try something? What makes you afraid?
9. If you could do something more, what would it be?
10. If you could go shopping right now with $100, what would you buy?

Road Trip Questions for Family About Personality

1. What is something you do really well?
2. What is something you wish you could do better?
3. How do you think you look at the world differently than other people do?
4. What makes you unique?
5. When have you learned that you’re different than other people?
6. What is something you’re proud of?
7. What are the different personalities in our family?
8. Who is someone who you think is a really good person? What makes them good?
9. Do you think our personalities can change?
10. How have you changed in how you think and act?