28 Funny "What Would You Do" Questions Worth Actually Arguing About

Most "what would you do" question lists are filler.

You've seen them. "What would you do if you won the lottery?" "What would you do if you could fly?" These are fine and harmless questions. Questions that produce exactly the answer you expected and end the conversation within 45 seconds.

This list is not that.

The questions below are funny, but they're funny in the way that good conversation games are funny. Unexpectedly and uncomfortably. In a way that makes someone laugh and then go quiet because they're actually thinking about it.

Each one comes with a note on why it works. Because the best "what would you do" questions aren't random. Instead, they're specifically designed to get past the polished answer and into the honest one.

The Questions

1. You find $500 in a jacket you haven't worn in two years. Do you tell your partner?

Why it works: Deceptively simple. Watch how fast it stops being about $500 and starts being about what people think they owe each other in relationships. The money is just the opening move.

2. A doctor tells you that you have exactly one year to live, but they've been wrong before, about 30% of the time. How do you spend the next month?

Why it works: The uncertainty is the point. It's not "what would you do with one year to live", it's what would you do when you're not sure. That 30% caveat changes everything.

3. You can have dinner with any person alive, but they have to genuinely want to be there too. Who do you pick?

Why it works: The constraint removes the fantasy. No celebrities who'd be bored. No historical figures. Just someone real, living, who would actually show up. Much harder than it sounds.

4. You wake up and everyone in the world has swapped bodies with the person they were most jealous of yesterday. Where do you end up?

Why it works: Requires honesty about something people rarely admit out loud. The funnier the answer, the more revealing it usually is.

5. A genie offers you the ability to know if anyone is lying to you, but you can never turn it off. Do you take it?

Why it works: Everyone immediately thinks they want this. Give it 10 seconds. The conversation about why you'd eventually want to turn it off is the real discussion.

6. You find out your closest friend has been slightly, harmlessly lying to you about one small thing for years, just to make you feel better. Do you want to know what it is?

Why it works: Splits the room every time. The people who say yes and the people who say no are revealing something real about how they handle truth.

7. You can eliminate one sound from existing permanently. What goes?

Why it works: Funny, low-stakes, and immediately generates strong opinions. Leaf blowers. Chewing. Notification sounds. Someone always picks something unexpected that makes everyone re-evaluate their own answer.

8. You're offered $10,000 to eat a food you hate every day for a year. What's the food, and do you do it?

Why it works: The food reveal is funny. The "do you do it" part is where it gets interesting because the answer says a lot about how people value money vs. daily quality of life.

9. You can go back and change one decision from your past, but you have to live with the butterfly effects. Do you go back?

Why it works: Better than "what's your biggest regret" because the butterfly clause forces people to weigh the trade-off honestly instead of just naming something sad.

10. Your best friend asks you to honestly rate their new business idea. It's not good at all. What do you actually say?

Why it works: Not hypothetical enough to feel safe. Practical enough to be uncomfortable. Most people discover mid-answer that they don't know what they'd actually do.

11. A stranger offers to tell you the exact date you're going to die, with no other information. Do you want to know?

Why it works: Classic for a reason. But the follow-up of "would you tell anyone else once you knew?" is where the conversation actually lives.

12. You can have one superpower, but everyone in the world gets it at the same time. What do you pick?

Why it works: The collective constraint makes it genuinely hard. Flying becomes useless. Mind reading becomes chaos. Watch people work through the second and third order effects in real time.

13. You find out that a movie you love was made by someone who later did something terrible. Do you watch it again?

Why it works: Not abstract anymore. Everyone has their own version of this sitting in their head. The question just gives them permission to say it out loud.

14. You can be instantly fluent in any language, but you permanently lose your ability to understand the main language you currently speak. Do you trade, and what's the deal?

Why it works: Forces a real cost-benefit calculation. Also reveals a lot about what people value: practical utility vs. cultural identity vs. keeping family connections.

15. Your employer offers you a 30% raise to work in a role you find incredibly boring but totally manageable. Do you take it?

Why it works: Splits along value lines immediately. The people who say yes without hesitation and the people who need to think about it are in completely different relationships with their work.

16. You can live anywhere in the world, all costs covered, but you can only visit your home country once a year, max. Where do you go, and do you do it?

Why it works: The "do you do it" clause is the real question. People who say yes without hesitation and people who pause at "twice a year" reveal something about what home means to them.

17. A scientist offers you a pill that removes your least favorite personality trait about yourself. Side effects might include removal of your favorite personality trait. Do you take it?

Why it works: Requires naming the trait first, which is already uncomfortable. Then requires deciding if you'd actually want to change it, which is more complicated than it sounds.

18. You find out your pet has been judging you silently for years. What do you think they've concluded?

Why it works: Funny on the surface, quietly self-aware underneath. The answers are almost always more honest than people intend them to be.

19. You can have unlimited money, but you have to spend it entirely within one category, no exceptions. What's the category?

Why it works: Reveals priorities immediately. Travel. Food. Experiences. Art. Real estate. The category someone picks without thinking is usually the category they'd pick if they thought about it forever.

20. Someone offers to tell you one true thing about how your closest friends really see you. Do you want to hear it?

Why it works: The people who say yes immediately and the people who hesitate are both right, and they'll argue about it for ten minutes.

21. You can be the best in the world at one thing, but only one person will ever know it's you. Do you still want it?

Why it works: Cuts straight to the question of whether people want achievement or recognition. The honest answer surprises most people.

22. A time machine lets you visit one moment from your past as an observer. You can't interact, just watch. Where do you go?

Why it works: "What would you do with a time machine" goes everywhere. This version constrains it beautifully. The moment people choose tells you more about them than almost any other answer.

23. You find out a close friend talks about you very differently behind your back than they do to your face, but not unkindly. Just differently. Do you want to know what they say?

Why it works: Subtler than the betrayal version. The "not unkindly, just differently" clause makes people actually think about what version of themselves they present vs. what version other people see.

24. You can add one hour to every day, but it only applies to you. No one else gets it. What do you do with it?

Why it works: The selfishness of the premise is built in. What you do with the hour reveals what you actually wish you had more time for, which is different from what you say you wish you had more time for.

25. Your life gets turned into a documentary. What's the most embarrassing scene?

Why it works: Funny, low-stakes, and almost always produces a genuine answer. People are oddly willing to share the embarrassing scene because it's framed as inevitable.

26. You can know the honest answer to one question about your future. What do you ask?

Why it works: Meta-hypothetical. The question someone asks reveals more than the answer ever would. Career. Relationship. Health. The choice is the answer.

27. A restaurant offers you a dish that's guaranteed to be the best thing you've ever eaten, but in turn you can never eat your current favorite food again. Do you order it?

Why it works: A real trade-off with a funny framing. The people who immediately say yes and the people who ask "what's the dish first" are fundamentally different types of people.

28. You can send one text to yourself from five years ago, but only 10 words. What do you send?

Why it works: The constraint forces real thought. Ten words is not enough to explain anything significant, so what do you actually say? The answers range from practical to devastating to surprisingly funny.

How to Use These (Without Killing the Mood)

A list of questions is only as good as how you use it. Here are some tips from the top conversation card games.

Don't go in order. Pick the ones that feel right for the room. The $500-in-the-jacket question is a different energy than the time machine question. Read where people are before you pick.

Let it get weird. The best "what would you do" conversations happen when someone's answer opens a question nobody expected. Follow the thread. Skip the next card.

Give a bad answer on purpose. The fastest way to make someone feel safe giving an honest answer is to give one yourself. Start with something dumb or self-deprecating. It gives everyone else permission.

Don't explain the question too much. The ambiguity is the point. Half the fun of "what would you do" is that people interpret the scenario differently, and arguing about the interpretation is usually the best part.

The Real Point of a Good Question

Here's what nobody says about "what would you do" questions: they're not really about what you would do.

They're about what you believe. What you value. What you're afraid of. What you've never admitted to yourself. And so on.

A good hypothetical is a shortcut past the polished version of a person and into the actual one. The best questions don't feel like questions at all. Instead, they feel like something that just happened, and now you have to decide.

That's why the weird ones work better than the safe ones. Safe questions get safe answers. Strange questions catch people being honest.

Go beyond funny "what would you do" and start asking the really weird questions

If you want access to the best talking games, including 197 bizarre, bold, unexpectedly thoughtful questions, then check out Are You Sitting Down?. It's the kind of weird conversation card game that pairs well with those funny "what would you do" conundrums. It makes people laugh, think, and finally say something true.