190 Thought Provoking Would You Rather Questions for Family
As a parent, I’d love more fun family conversations that connect everyone from grandparents to grandchildren. 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 and family-friendly would you rather 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.
Silly questions like ‘Would you rather have spaghetti for hair or marshmallows for hands?‘ have been skipped in favour of more thought-provoking and engaging inquires to ensure that adults do not find them tedious.
The questions are organised into ten 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
- 7. Light Hearted Ethical Dilemma Questions
- 8. Serious Ethical Dilemma Questions
- 9. Family and Relationships Questions
- 10. Bonus For Parents: Family Legacy & Meaningful Connections Questions
- It’s A Fun Game That Shares Our Values
- Download All Questions
- 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:
- With a question master: A question master should choose one question for family members in turn.
- Take turns to ask a question: Everyone takes turns choosing a question to ask a family member.
- 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.
- Take turns answering each question on the list: Go down the list, taking turns to answer questions.
- 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 imaginative conversations that help you discover new things about each other and strengthen your family bonds.
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 be an unknown superhero or a famous villain?
- Would you rather take a risk and fail or play it safe and never know?
- 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 Arctic?
- 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 extra in a really good movie or have a big part in a terrible movie?
- Would you rather have a personal chef or a personal driver?
- Would you prefer to always be slightly overdressed or a bit underdressed?
- Would you rather be the smartest person in the room or the funniest?
- Would you rather live a simple life with little stress or a busy life with high rewards?
- Would you rather give up your favourite hobby or your favourite food?
Turn everyday moments into lifelong memories in Simirity
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 have a small circle of close friends or a large group of acquaintances?
- Would you rather always be the centre of attention or prefer to stay unnoticed in social gatherings?
- Would you rather always have to agree with everyone or never be able to agree with anyone?
- Would you rather attend a party where you know everyone but it’s dull, or a party where you know no one but it’s lively?
- Would you rather live in a world where everyone is overly polite or overly honest?
- Would you rather always have to share your personal achievements publicly or keep them entirely to yourself?
- 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?
Not another chat app—Simirity is for deeper family connections.
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 always have a tidy home but be disorganised personally, or be personally organised but have a messy home?
- Would you rather live in a tiny home in your dream location or a mansion in a place you dislike?
- Would you rather follow a strict routine every day or have complete spontaneity in your schedule?
- Would you rather always have to dress formally or always wear casual clothes?
- 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?
Feel together, even when you can’t be together with Simirity.
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 light hearted 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?
- Would you rather have the wisdom of age or the energy of youth?
- Would you rather achieve all your goals but feel unfulfilled, or achieve none but feel content?
- Would you rather spend your life achieving personal goals or helping others achieve theirs?
- Would you rather face your biggest fear once or be slightly afraid of it every day?
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 have a photographic memory or be able to forget any unwanted memory?
- Would you rather always know the truth or always be able to lie without being caught?
- Would you rather be able to heal others or heal yourself?
Simirity—Because one day, these moments will mean EVERYTHING
7. Light Hearted Ethical Dilemma Questions
Ethical dilemmas don’t have to be serious—they can also be entertaining and delightfully tricky! These light hearted scenarios are all about the kind of choices that get people smiling, debating, and sharing stories. Perfect for breaking the ice or adding a little fun to family conversations.
Would you rather know everything about your family’s history or let them keep their secrets?
— Simirity
- Would you rather share your dessert with everyone or eat it all yourself but feel guilty?
- Would you rather steal a parking spot from someone or park farther away and be late?
- Would you rather let someone cut in line or hold your ground and risk confrontation?
- Would you rather secretly re-gift a present you don’t like or keep it and never use it?
- Would you rather pretend to like a meal someone cooked for you or tell them it wasn’t your favourite?
- Would you rather find money on the street and keep it or turn it into lost and found?
- Would you rather tell your friend you don’t like their new haircut or let them think it looks amazing?
- Would you rather take the last piece of pizza in front of everyone or wait and hope someone else doesn’t take it first?
- Would you rather not correct a waiter who gave you too much change or point it out and look honest?
- Would you rather cut the line at a concert or wait patiently and miss the best spots?
- Would you rather finish the milk and not replace it or leave just a drop so someone else has to?
- Would you rather ignore a call from a family member during dinner or answer and be distracted?
- Would you rather fake being sick to skip a boring event or go and hope it’s more fun than you thought?
- Would you rather let a family member wear something embarrassing to an event or tell them and make them self-conscious?
- Would you rather peek at someone’s diary if they left it open or close it and walk away?
- Would you rather tell someone their zipper is down or let them find out on their own?
Go beyond “How are you?”—truly connect with family in Simirity.
8. Serious Ethical Dilemma Questions
Life is filled with tough decisions that challenge our morals, values, and priorities. Serious ethical dilemmas push us to think deeply about what we believe is right or wrong, even when the answer isn’t easy. These questions will help you understand how your family approaches life’s most difficult choices.
Would you rather uncover a devastating truth about a loved one or live in blissful ignorance?
— Simirity
- Would you rather tell a harsh truth that hurts someone or a comforting lie that makes them feel good?
- Would you rather sacrifice one person to save many or not take action and allow many to suffer?
- Would you rather steal to feed your family or let them go hungry?
- Would you rather tell a painful truth or a comforting lie?
- Would you rather break a promise to help someone or keep your promise but let them struggle?
- Would you rather sacrifice your own happiness to make someone else happy or prioritize your own joy?
- Would you rather always follow the rules but feel restricted, or break the rules to do what feels right?
- Would you rather risk your life to save someone else or stay safe but always regret it?
- Would you rather do something illegal for the greater good or stay lawful and let others suffer?
- Would you rather forgive someone who deeply hurt you or hold a grudge forever?
- Would you rather lose something valuable to you or take something valuable from someone else?
- Would you rather confront a friend who is doing something wrong or ignore it to keep the peace?
- Would you rather stand up for what’s right but risk losing friends or stay silent and keep them close?
- Would you rather help someone you dislike or ignore their need for help?
- Would you rather cheat to succeed or fail but know you were honest?
- Would you rather lie to protect someone’s feelings or tell the truth and hurt them?
- Would you rather let one person take credit for your work or publicly fight for recognition?
9. Family and Relationships Questions
These questions dive into the little dynamics, values, and connections that make your bonds special. Whether you’re sharing laughs, memories, or insights, these “Would You Rather” questions are a chance to learn more about the people closest to you—and maybe even about yourself.
Would you rather have a family member criticise your every decision or never give you any feedback at all?
— Simirity
- Would you rather always have family game nights or always have family movie nights?
- Would you rather live close to your family but have a busy schedule or live far away but have plenty of free time?
- Would you rather never have a family argument or always win every argument?
- Would you rather have a family member forget your birthday or forget theirs?
- Would you rather always be the one planning family events or just show up to them?
- Would you rather have a sibling who is always in your business or one who never talks to you?
- Would you rather have a family reunion once a year or smaller gatherings every month?
- Would you rather always get advice from your family or figure things out on your own?
- Would you rather have one amazing fortnight with your family every year or shorter, great moments every week?
- Would you rather have a family member you always agree with or one who always challenges your ideas?
- Would you rather have a sibling who always plays pranks on you or one who is overly serious?
- Would you rather spend your holidays at home with family or travel to a new place every year?
- Would you rather have family photos displayed in every room of your house or no family photos at all?
- Would you rather always host family gatherings or always attend them?
- Would you rather have one sibling or five siblings?
- Would you rather have a family road trip every year or a staycation with them every year?
Your family’s past, present & future—woven together in Simirity
10. Bonus For Parents: Family Legacy & Meaningful Connections Questions
These thought-provoking questions invite parents to consider what truly matters in family connections—both today and for future generations.
After each question, discover how the Simirity app can transform your answer from wishful thinking into family reality.
- Would you rather have your parents’ wisdom and life lessons preserved in their own words, or trust that you’ll remember everything they taught you?
👉 Simirity creates a permanent home for your family’s wisdom that can be shared across generations. - Would you rather have meaningful weekly conversations with family living elsewhere, or stick to the same “what have you been up to” small talk every call?
👉 Simirity helps families discover new topics to discuss, creating deeper connections despite distance. - Would you rather give your future grandchildren authentic insights into your life today, or let them wonder what you were really like?
👉 Simirity helps you leave a genuine legacy beyond just photos – your thoughts, values, and stories included. - Would you rather have your family’s precious memories organised in one private place, or scattered across various social media platforms (or not saved at all)?
👉 Simirity helps unlock the deeper stories that shaped your family’s core beliefs and traditions. - Would you rather have your children hear about their heritage directly from their grandparents, or have those stories lost when they’re gone?
👉 Simirity preserves grandparents’ stories in their own voices for future generations to discover. - Would you rather truly know your family members’ hopes, dreams and struggles, or maintain polite but shallow relationships?
👉 Simirity creates opportunities to share deeper aspects of ourselves that strengthen family bonds. - Would you rather capture the story behind a moment in your child’s life, or just have another photo in an endless digital album?
👉 Unlike photo albums, Simirity preserves not just what happened, but how it felt and why it mattered. And with voice narrations for photos, every detail you care about can be preserved with ease. - Would you rather have detailed stories about your grandparents’ lives that you can share with your children, or just a handful of undated photos with no context?
👉 With Simirity, your grandparents’ experiences become vivid stories, not just faded images. - Would you rather have your children understand their family roots and identity, or grow up disconnected from their extended family heritage?
👉 Through Simirity, give your children the gift of knowing where they come from and who came before them. - Would you rather discover new dimensions to your parents’ personalities through their past experiences, or always see them only as “Mom and Dad”?
👉 Simirity reveals the full, fascinating people your parents were before you knew them. - Would you rather know the real stories behind your family heirlooms, or simply inherit objects with no understanding of their significance?
👉 With Simirity, family heirlooms carry their full history and emotional significance to the next generation.
These questions highlight what’s at stake—and why families like yours are using Simirity to preserve the stories that matter, deepen family connections, and build a precious legacy for their children and future generations.
Simirity is your family’s digital scrapbook of memories.
Beyond photos, videos and voice notes, Simirity app uses real-life stories from your family’s past and present to enrich family relationships while storing cherished memories for tomorrow.
Your stories blossom into rewarding conversations that take your family beyond everyday small talk—creating moments of genuine connection that you’ll treasure forever.
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.
Download All Questions
Download our free print-friendly PDF containing all these ‘would you rather’ questions. Highlight your favourites and bring them to your next family gathering.
We really hope this sparks some wonderful family conversations! If you love these family chats that go beyond the usual topics, keep reading…
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:
- Story prompts that give interesting ideas for family stories you can share and preserve for future family.
- 350+ thought-provoking questions to ask your mom and dad – this is a must read for anyone who would like to connect with their parents by exploring their past.
- Digital storytelling for families – together, capture the laughter, voices, and little details that make your family unique.
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.
Keep your kids connected to their roots with Simirity.
