The best family would you rather questions are silly and easy to answer in one breath. A six-year-old can pick a side, and a grandparent can say why. Start with a superpower, a talent or a food, and save the heavier ones for later in the evening.
Here are three to try right now:
- Would you rather have the ability to fly or be invisible?
- Would you rather always have to sing instead of talk, or always dance instead of walk?
- Would you rather be able to talk to plants or talk to insects?
Read one out, assign each answer to the left or right, count to three, and have everybody point at their answer at the same time. That’s one round.
Every question here comes from Lolo Cards - 5,200+ conversation cards for iPhone.
Why this game works when ages are mixed
At a big family table, somebody may not be able to read the cards yet, somebody may struggle with the small print, and somebody may know the game so well they win every time.
You can play would you rather without keeping score. Read each question aloud so nobody has to read the cards. A child’s answer counts as much as an adult’s, and the fun is in hearing why.
Lisa Kervin, Director of Early Start Research at the University of Wollongong, says intergenerational play offers “many benefits to young and old” and that play helps maintain memory and problem solving in older adults. This is her summary of the research, not a promise about what a game night will do.
In a piece on family game nights from the University of Calgary, education researcher Hetty Roessingh writes, “What matters is taking turns in conversation.” Give everybody a turn and room to answer.
Start with the silly ones
Open with silly questions and let the youngest player answer first:
- Would you rather always have to whisper or always have to shout?
- Would you rather be able to teleport anywhere or freeze time whenever you want?
- Would you rather be able to breathe underwater or survive without sleep?
If a small child says “invisible, so I can eat all the cookies,” ask what the first cookie would be. A follow-up gives them room to say more.
If you want more of these, the full would you rather hub has funny, crazy, food and hard questions in separate lists.

Four ways to turn questions into rounds
Try one of these formats:
- Point on three. Read the question, assign each answer to the left or right, count to three, and everyone points at the same time.
- Guess the answer. One player chooses an answer without saying it, and the others guess what they picked. Then the player reveals their answer.
- Make the opposite case. Ask somebody to defend the option they didn’t pick, for ten seconds.
- Let the youngest invent one. Give a kid a turn to make up a question for the grown-ups. Take it seriously.
Questions for the grown-ups and grandparents
Once the little ones are warmed up, try questions that give the grown-ups and grandparents more to explain. Invite teens to answer too.
- Would you rather live without dessert forever or without your morning coffee forever?
- Would you rather live somewhere with amazing food and bad weather, or bad food and amazing weather?
- Would you rather always know what to say or always know what to do?
The last one is worth slowing down for. Let a grandparent answer first, and then ask when they last needed to know what to do. Leave room for a story if they want to tell one.
For a quieter evening with more time for the “why,” the questions to ask your grandparents hub has questions about their life. You can also borrow ideas from our family dinner conversation starters.

Keep it light, and keep it short
A few habits to try:
- Stop while it’s still fun. Ten questions is plenty.
- Allow a pass. Nobody has to explain an answer, and if a question lands somewhere tender, move to the next one.
- Skip the score.
- Keep the phones down, except the one holding the questions.
If you’re curious about someone’s choice, ask why and give them room to answer or pass.
Pick one, and ask it tonight
Pick the funniest question from the list above and read it out at dinner or on the sofa. Start with one round, then ask whether everyone wants another.