100 Thought Provoking Would You Rather Questions for Family

As a parent, I’d love more fun conversations that connect my parents to my children. But it’s not always easy.

Interests differ from Minecraft to motorhomes, attention spans can be limited and some family members don’t get to speak much. For me, the Holly Grail would be a fun family conversation where we learn something interesting about each other. I discovered that ‘would you rather…’ questions are a great kid-friendly and grandparent-friendly way to achieve this.

We’ve pulled some great questions and crafted our own to make the ultimate list of thought-provoking family-friendly questions. We have been searching for fun questions suitable for everyone over the age of 10, with the added benefit of helping family members get to know each other better.

We’ve specifically chosen more thought-provoking and interesting questions than silly ones, to ensure adults don’t find them tedious.

The questions are organised into six categories ranging from Adventure to Skills and Superpowers. 

Jump to section:

• How to Use Would You Rather Questions for Family
• 1. Personal Choice Questions
• 2. Social Questions
• 3. Adventure Questions
• 4. Lifestyle Questions
• 5. Personal Growth and Life Reflections Questions
• 6. Skills and Superpowers Questions
• It’s A Fun Game That Shares Our Values
• Preserve Family Fun With Simirity App
• Other Ways to Connect With Your Family

How to Use Would You Rather Questions for Family

Get to know your family with fun and thought-provoking questions using one of these methods:

1. With a question master: A question master should choose one question for family members in turn.
2. Take turns to ask a question: Everyone takes turns choosing a question to ask a family member.
3. Take turns picking a question: Everyone takes turns choosing a question from the list to answer. This is a little easier for family members as they get to decide what they are ready to talk about.
4. Take turns answering each question on the list: Go down the list, taking turns to answer questions.
5. Answer all questions together: Go down the list together, answering all the questions

These questions can be great for family game night or over family dinner, but they are especially helpful on video calls where children can quickly disengage from the conversation.  

Asking ‘why’ family members gave that answer is a great way to get the conversation flowing and learn more about how they make decisions. Encourage others to share their views, to get everyone talking. 

We hope these questions spark some imaginative and unusual conversations that help you get to know each other better.

1. Personal Choice Questions 

These questions help kids think about what is important in their lives and gives them interesting references about their family members.

Would you rather never read a book again or never watch a movie?

— Simirity

• Would you rather have the very best clothes or the very best technology?
• Would you rather live without your mobile or your computer? 
• Would you rather have one gift worth $1,200 or a $100 gift every month for one year? 
• Would you rather get $100 dollars or 100 lottery tickets?
• Would you rather face the heat of the desert or the cold of the artic?  
• Would you rather be a great chef who loves his job or have a great chef cook for you? 
• Would you rather go to jail for a year or be homeless for a year?
• Would you rather have one wish granted today or three wishes granted ten years from now?
• Would you rather be on a losing team with friends or join your rival team and win the competition?
• Would you rather be forced to sing along to every song you hear or dance to every song you hear?
• Would you rather solve climate change or end all fighting around the world? 
• Would you rather predict the future or remember everything you have ever done?
• Would you rather live in a world without music or without TV?
• Would you rather cheat at a game and win or lose but know you tried your best?
• Would you rather eat at your favourite local restaurant or a new restaurant that just opened?
• Would you rather live in a world run by elected teenagers or a world run by one well-educated adult randomly selected every 15 years?
• Would you rather make $1 million yearly as a famous YouTuber or an anonymous author?
• Would you rather someone borrowed $500 and never returned it, or someone lent you $500, and you never repaid it?
• Would you rather lose your sight or your memories?
• Would you rather give up home heating and air conditioning or the Internet?
• Would you rather lose all of your teeth or all of your hair?
• Would you rather never use social media or never watch movies again?
• Would you rather never stand in a queue or always have traffic lights turn green when your car approaches?
• Would you rather lose your long-term memory or your short-term memory?
• Would you rather spend weekends indoors or weekends outdoors?
• Would you rather be an unknown superhero or a famous villain?
• Would you rather be an extra in a really good movie or have a big part in a terrible movie?

2. Social Questions 

These are questions to learn about people’s preferences in a social context and share your views about topics like the pros and cons of fame or the importance of friends.

Would you rather meet people who are famous today, or people who will be famous in a year from now?

— Simirity

• Would you rather know when people lie or not know when they lie to you? 
• Would you rather get a postcard every day from a stranger in a different country or a 10-minute call with anyone in the world you choose once a year?
• Would you rather be stranded on an island with someone you dislike or stranded on an island alone?
• Would you rather never be able to say what is on your mind or always have to speak the truth? 
• Would you rather be homeless and have family and friends or live comfortably but entirely alone?
• Would you rather be famous but have no privacy, or adored by only 10 people but live in private? 
• Would you rather travel back in time to meet your ancestors or forward in time to meet your descendants?
• Would you rather always be 10 minutes late or 20 minutes early to meet people?
• Would you rather be on a reality TV program showing your life 24-7 or live alone in isolation?
• Would you rather have 100 friends online that you have never met or one friend you can meet in person?

3. Adventure Questions 

These are questions for kids to get excited about as they imagine interesting future possibilities. As adults, you might have additional context to share on some of these questions, adding interest and education to your conversation.

Would you rather visit 100 countries for a short time or get to live in 5 countries? 

— Simirity

• Would you rather walk the Great Wall of China or boat down the Amazon River?
• Would you rather be able to travel back or forward in time? 
• Would you rather have unlimited international first-class tickets or never have to pay for restaurant food?
• Would you rather spend a day exploring space on a rocket ship or diving deep in a submarine?
• Would you rather spend a week camping in the wilderness or relaxing on a luxurious cruise ship? 
• Would you rather spend a day exploring the most beautiful nature spot or the most advanced city? 
• Would you rather start a colony on Mars or be the leader of a country?
• Would you rather travel the world for free for a year or be given $50,000 to spend however you please?

4. Lifestyle Questions

This collection of questions paints a picture of how your family would like to lead their lives. It gets them thinking about the future and how their friends and family fit into it.

Would you rather have your dream home or the ability to travel as often as you want?

— Simirity

• Would you rather live somewhere hot or cold all year round?
• Would you rather experience a wonderful life to the age of 100, or spend 100 years at any age you choose?
• Would you rather be born again in the same country or a different one of your choosing?
• Would you rather live in a country with four distinct seasons or in a country always sunny and warm? 
• Would you rather work really hard for 10 months and have a 2-month dream holiday, or have 12 months relaxing at home but no holiday?
• Would you rather live by the beach or in the mountains? 
• Would you rather live in a castle with secret passages or a modern mansion with all the latest technology? 
• Would you rather live in a cave or live in a tree house?
• Would you rather have a completely automated home or a self-driving car?
• Would you rather have location freedom or time freedom?
• Would you rather have a 3-day weekend each week but no additional days off or two-day weekends and 10 weeks off a year? 
• Would you rather have a cook or a maid?
• Would you rather be able to eat as much as you want and never gain weight or feel refreshed and well-rested after only three hours of sleep each night?
• Would you rather be the luckiest person alive or know you worked hard for what you have?
• Would you rather live your entire life in a virtual reality where everything you wish for comes true or just in the normal real world?
• Would you rather have an amazing job that pays poorly or do something you hate that pays a lot?
• Would you rather have a noisy neighbour or a nosy neighbour?
• Would you rather live without running water or no internet?
• Would you rather have lots of energy or have lots of money?

5. Personal Growth and Life Reflections Questions

These questions are a fun way to get kids, parents and grandparents alike, thinking about what is important in life. Encourage debate by challenging others’ points of view.

It’s a far better parenting strategy to ask fun questions like these and exchange views in a lighthearted context, than preach the virtues of things like education and contributing to society.

It’s also a set of questions that always brings a few surprises and unexpected viewpoints!

Would you rather be a genius everyone thinks is an idiot or an idiot everyone thinks is a genius?

— Simirity

• Would you rather have the chance to travel the world for a year or speak 10 languages fluently?
• Would you rather have the chance to fix your biggest mistake or never make a mistake again?
• Would you rather be very intelligent or really attractive?
• Would you rather have no photos but clearly remember all the places you visited, or no memories but lots of photos? 
• Would you rather have amazing dreams each night that you can’t remember or very occasional dreams that you can remember forever? 
• Would you rather be told all the great things that will happen in your life, or wait and be surprised when they happen? 
• Would you rather win the Nobel Peace Prize or 5 million dollars?
• Would you rather go back to age 5 with everything you know now or know now everything your future self will learn?
• Would you rather everyone in the world be kinder or more intelligent?
• Would you rather never grow old or never worry about money?
• Would you rather receive a top award for a work of art you created or a scientific invention?
• Would you rather ask for help with a difficult task or figure out how to do it yourself?
• Would you rather have a pause button for your life or a rewind button?

6. Skills and Superpowers Questions

These rather funny would you rather questions get the conversation flowing into areas you probably never explored before. Though hypothetical, the answers say a lot about what your family members value and their decision-making process.

Would you rather have the ability to talk with your past self or your future self? 

— Simirity

• Would you rather be able to control animals with your mind or control electronics with your mind?
• Would you rather have world-class skills in writing stories or writing music? 
• Would you rather have the ability to read other people’s minds or see into the future?
• Would you rather be a world expert at one particular subject or have a broad understanding of thousands of subjects? 
• Would you rather be the boss or the employee?
• Would you rather be able to overcome all your bad habits, or be able to help everyone else overcome theirs?
• Would you rather have super sight or super taste?
• Would you rather be able to talk to plants or animals?
• Would you rather have the power to bring fictional characters to life or travel into fictional worlds yourself? 
• Would you rather have the ability to control the weather in your immediate vicinity or control the emotions of those around you? 
• Would you rather be able to learn any subject super fast or develop any physical skill super fast? 
• Would you rather receive a performance upgrade for your brain or your body?
• Would you rather have the ability to fly but only at a walking pace, or run at superhuman speed but only be able to stop once you reach your destination? 
• Would you rather be able to see into other people’s futures or your own?
• Would you rather have a photographic memory or be super intelligent?
• Would you rather be completely invisible for one day or be able to fly for one day?
• Would you rather have the ability to move things with your mind (telekinesis) or the ability to read minds (telepathy)?
• Would you rather have eyes that can capture everything on video or ears that can record all sounds?

Would You Rather Questions is a Fun Game For Sharing Our Values

The answers to ‘would you rather’ questions expose our personal values. Sometimes it’s hard, as we’re pitching values against one another. Even seemingly silly questions like the one below inform us about their value system:

Would you rather be an unknown superhero or a famous villain?

— Simirity

Will their desire to do the right thing and help others outweigh their desire for recognition and power? I can see in our own family how effective this game is at sharing our views on healthy values for a happy life with our children. 

Playing this game is super fun, but it also teaches a lot about life while revealing new insights about your family.

Preserve Your Family Discoveries With Simirity App

Wouldn’t preserving some of these entertaining answers as audio recordings would be nice? The best would you rather questions can teach you new things about people as well as initiating conversations that you’ll treasure for the rest of your life.

Preserve your family’s answers, and in years to come:

• Your kids could look back at how they used to think. 
• Everyone can listen to old stories and relive those times.
• You can hear happy, laughter-filled conversations with people who may no longer be with you. 

Simirity App is a private storytelling app that unites your extended family in stories, even if you live apart.

Over time, your entire family can build an archive of digital stories, filled with memorable photos, videos and audio, that share your experiences with young generations.

Create digital stories that include audio recordings of up to 30 minutes. Add photos and videos if you have any. Write about the time together and tag the family members present. Then, publish the story to a private library filled with family stories.

Every year on the anniversary of that story, enjoy receiving a story notification reminding you of the good times you shared. Happy memories, appreciated again and again.

If you would like to learn more about Simirity App, visit our home page.

Other Ways to Connect With Your Family

Would you rather questions are a great way to discover interesting subjects to discuss with your family. You can even use them over a video call if you live apart. If you enjoy exploring new and diverse topics with your family, why not also try:

1. Story Prompts that give interesting ideas for family stories you can share and preserve for future family.
2. 57 meaningful questions for parents.

Meaningful conversations like these are the ones you will cherish for the rest of your life. It’s easy to get stuck in a rut and have the same old family discussions – escape mundane conversations and connect more deeply with your family.