200+ Conversation Starters for Family Vacations

July 14, 2023

Planning a family getaway? Getting away together as a family can be a great opportunity to “check in” with your kids. Whether you are touring a city, skiing the slopes, flopping down on a beach or visiting the theme parks, be intentional about starting conversations with your kids while taking a break from your everyday lives.

I’ve included a curated list of more than 200 conversation starters to help you keep the conversation going. From silly “Would You Rather” questions to deeper, more reflective questions, there’s a conversation starter for every family type.

Waiting in line for Slinky Dog Dash or having a family meal? Introduce some Would You Rather or Getting to Know You questions. Have 5-10 minutes of downtime with one child? Do a quick “check-in” by picking some age appropriate questions from the School, Friends or Relationships categories.

Conversation Starter Tips

Listen. The purpose of conversation starters is to get your family off of their devices and talking with one another. That means listening to one another. Your children will notice if you are distracted and not paying attention to what they are sharing. Even if it’s the answer to a silly “I’d Rather” question, pay attention. Memories are made here!
Go Deeper. Draw out their responses by asking more questions about what they’ve shared, such as: Oh really? Why do you suppose that is? Tell me more about _____.
Participate. Share your answers to the questions as well. For school or friendship related questions, you could share stories from when you were their age and how you handled certain situations. You might add whether or not you would have done things differently now. Keep these stories brief, and use your judgment to determine what is appropriate to share. You can always continue the conversation when you are home if something comes up that needs more attention, such as “Remember when you mentioned ______ on our family vacation? I’ve been thinking more about it and wanted to ask you _____.”
No Lectures. Some of the following questions may stir up deeper thoughts, feelings or ideas that are surprising or different from your own. Just listen. Create safe, non-judgemental spaces for sharing so that your child will open up. Some of these questions can lead to teachable moments, but as a rule, listen more than lecture. You can always circle back to the topic at a later time if there’s something that truly needs to be addressed.
Have Fun! Share. Plan. Dream. Bond. But most of all have fun creating new memories and deeper connections!

About Your Family Vacation Questions:

What are you looking forward to most today?
What are you looking forward to most on this vacation?
If you could go anywhere in the world – where would you go?
Where should we go on our next family vacation?
What do you think will be your favorite food on this vacation?
Do you think experiences (traveling, vacations, making memories, ect) or things (toys, new technology, clothes, ect) are most important? Why?

Getting to Know You Questions:

If you could have any animal as a pet which would you choose?
Why is your favorite color your favorite color?
If you could have one superpower what would it be?
Who is your favorite Disney character? Why?
Who is your favorite Star Wars character? Why?
Who is your favorite superhero? Why?
What mythical creature do you wish actually existed?
What’s the funniest joke you know by heart?
What game have you spent the most hours playing?
Do you think it would be fun to be famous?
If you could go into any TV show – what show would want to visit?
What movie always makes you laugh?
If you had three wishes, what would they be? (Not money or another wish-be creative!)
What cartoon character would you want to live with?
Show your funniest face!
If you had to pick a new name for yourself, what would it be?
If you design your own playground, what would you include?
What weird food combinations do you really enjoy?
What do you want to invent?
What is the best compliment you’ve ever gotten? Who gave it to you?
What is the one thing you think you couldn’t live without?
What is the best thing about being ______ years old?
What is the hardest thing about being _____ years old?
If you could only be one age for the rest of your life – what age would you want to be?
What would your perfect day be like?
Can you remember a time when you had a really good day?
What job would you never want to have?
How many children would you like to have one day?
What is your favorite thing about yourself?
Are you a "cup is half full" or "cup is half empty" kind of person?
What is one thing that you would like to learn how to do?
What do you think you are good at?
What do you know how to do that you could teach someone else?
If you could be great at something, what would you want to be great at?
If you could turn someone nice, who would it be?
If you could make one change to improve the world, what would it be?
What is a quality you wish you could have more of?
What is your biggest goal this year?
Name five reasons you’re glad to be alive.

Parent-Child Relationship Questions:

What is your favorite thing about our relationship?
What is your least favorite thing about our relationship?
Do you feel like you could talk with me about anything at all?
What would you be most likely to want to lie to me about? Why?
If you got into really big trouble, how do you think I would respond?
Is there something I can do better as your parent that I am not doing now?
If we had a special day together what would you want to do?
What are the most important things I have taught you?
If you had to choose only three words to describe me as a parent, what would you say?
Do I ever embarrass you?
If you and I could switch places for a day, what are the first things you would do?
What’s one rule you wish we didn’t have?
If you were the parent, what lesson would you like to help us learn?
What is something you wish I would do more often?
Less often?
Are you able to tell me or others when you are upset?
How do you feel when someone is angry with you? How do you act?
What do you do to cheer yourself up when you feel down?
What words do you wish someone would say to you when you’re having a tough time?
Have I never not noticed when you're sad?
What is the best way for me to help you when you feel grumpy?
What hurts your feelings? How do you act when your feelings are hurt?
When you're upset, do you like me to stay close or give you some space?
When you get really angry, how do you help yourself calm down?
When you are really angry at me, what is the most helpful way for me to respond?
What do you worry about the most

Family Matter Questions:

Do you know how much your family loves you? How can you tell?
What relative do you love seeing the most?
How do you think your friends' families compare to ours? Are they about as close? Closer? More distant? Why do you think that?
Do you think your friends talk to their parents?
What do you think makes a family close?
On a scale of 1 to 10, how strict are the parents in this family? What is the ideal number?
Is the discipline in our family fair?
What should a parent do when their children don’t obey?
What’s the best thing about our family?
What do you think makes a happy family?
Tell each person in the family why you’re glad they’re part of the family.
How do you think our family is the same or different from other families?
Do you want to have kids when you grow up? Why or why not?
What kind of parent will you be?
What are the good things about having siblings? What are the bad things?
What is the most important thing to do to have a good relationship with a sibling?
Do you have better or worse relationships with your sibling(s) than your friends?
Do you think you will be close to your siblings when you grow up?
How many of your ancestors can you name and what do you know about them?
How are you like each of your parents? How are you different?
What is your favorite family tradition?
What three words (or more) do you think best describe our family?

School Life Questions:

What do you normally do during recess?
What class/subject do your look forward to?
What class/subject do you dread?
Who is or was your favorite teacher? Why?
What do you like best about school?
What’s the hardest part about going to school?
What is your favorite time of the school day?
Have you helped anyone at school recently? Has anyone helped you?
Have you had a chance to be kind to anyone recently? Has anyone been kind to you? Is it hard to make the choice to be kind sometimes?
What is your strategy to manage your homework so you can stay on top of it?
What is the most embarrassing thing that ever happened to you at school?
Do you respect your teachers? Why or why not? Do you think they respect you?
Would you ever want to be a teacher? Why or why not?
What do you think makes the most difference in how kids do at school? Is it the student’s effort, how smart they are, parental supervision, attitudes of their friends, how good the school is?

Friendship Questions:

What traits do you most admire in other people?
Who is the nicest person you know?
Who is your best friend? Why are they your best friend?
How do you make friends?
Do you have any friends you’re worried about right now?
Are you happy with the number of friends you have?
Do you ever feel lonely or left out?
What makes a good friend?
Who in your class is a really good friend to others?
What makes someone a bad friend?
Has anyone ever been a bad friend to you?
What does it mean to be popular at your school?
Do you want to be popular?
Who do you wish would listen more closely to you?
Who do you usually sit with at lunch at school? What do you talk about?
Who is your best friend and why?
What traits do you look for in friends?
Where do you consider yourself on the shy to outgoing scale?
Have you ever been mad at one of your friends? How did you handle it?
Is there anyone at school that you would like to get to know better?
Is there anyone at school that seems to get left out or teased a lot?
Do you have friends who are different races or religions than you? Does that have any effect on the friendship?
Do you think there is a such thing as peer pressure? Do you ever feel peer pressure? Do you think some people are more susceptible to peer pressure than others? Why do you think that is?

Love and Marriage Questions:

At what age do you think people can fall in love?
At what age should people marry?
How do you think love is different in real life than it is in the movies?
What would be most important thing to you in spouse?
What are the top 5 qualities you would look for in a spouse?
What quality would you absolutely not want in a spouse?
Do your friends have boyfriends/girlfriends?
Is there anyone you have a crush on?
What do you like about them?
Is there anything about them that might be a “red flag” or you’re not sure about?

Faith Questions:

How would you describe God?
What types of things do you pray for?
What do you think happens after death?
What do you think is the meaning of life? Why are we alive?
Do you have any questions about what we believe?

Would You Rather Questions:

Would you rather live at the beach or the mountains?
Would you rather see a fireworks display or circus performance?
Would you rather eat your least favorite vegetable or have extra homework?
If you had to pick only one – would you want to be a great singer or a great dancer?
If you had to have no arms or no legs – which would you pick?
Would you rather fly or be able to read minds?
Would you rather learn to water ski or snow ski?
Would you rather visit the international space station for a week or stay in an underwater hotel for a week?
Would you rather be able to see things far away like binoculars or see things close up like a microscope?
Would you rather be incredibly funny or incredibly smart?
Would you rather be able to control fire or water?
Would you rather be able to remember everything you’ve ever seen or heard or be able to perfectly imitate any voice you heard?
Would you rather drink every meal as a smoothie or never be able to eat food that has been cooked?
Would you rather meet your favorite celebrity or be on a TV show?
Would you rather be able to shrink down to the size of an ant any time you wanted to or be able to grow to the size of a two-story building anytime you wanted to?
Would you rather live your entire life in a virtual reality where all your wishes are granted or in the real world?
Would you rather do a book report or a science project?
Would you rather build a sandcastle or build a snowman?
Would you rather live without the internet or live without AC and heating?
Would you rather give up watching TV / movies for a year or give up playing games for a year?
Would you rather be forced to dance every time you heard music or be forced to sing along to any song you heard?
Would you rather be the youngest or the oldest sibling?
Would you rather be the most popular person at work or school or the smartest?
Would you rather be too busy or be bored?
Would you rather be poor and work at a job you love, or rich and work at a job you hate?
Would you rather have telepathy or telekinesis?
Would you rather have a cook or a maid?
Would you rather live in Narnia or go to school at Hogwarts?
Would you rather go into the past and meet your ancestors or go into the future and meet your great-great grandchildren?
Would you rather have to sew all your clothes or grow your own food?
Would you rather read an awesome book or watch a good movie?
Would you rather win the lottery or live twice as long?
Would you rather have a family of 12 children or never be able to have children at all?
Would you rather spend the night in a luxury hotel room or camping surrounded by beautiful scenery?
Would you rather win the lottery or live twice as long?
Would you rather be always dressed up or always in your pajamas?
Would you rather be a doctor or a scientist?
For your birthday, would you rather receive cash or gifts?
Would you rather go to a movie or to dinner alone?
Would you rather go without TV or junk food the rest of your life?
Would you rather give up bathing for a month or give up the internet for a month?
Would you rather know everything or be amazing at any activity you tried?
Would you rather live in a place where it is always hot or always cold?
Would you rather go on the world’s tallest roller coaster or go skydiving?
Would you rather visit a zoo or an aquarium?
Would you rather change your eye color or your hair color?
Would you rather take an action-packed European vacation or spend two weeks at the same Caribbean resort?
Would you rather hear the good news or the bad news first?
Would you rather be an art teacher or PE teacher?
Would you rather have a blue nose or purple ears?
Would you rather have a pet dinosaur or pet dragon?
Would you rather have 5 brothers or 5 sisters?