Here are some really fun questions to ask and answer. They cover all kinds of different subjects, so there are sure to be some that’ll be perfect for you and the person you’re talking to.

We’ve got some more links to other fun questions to ask at the bottom of the page, so don’t forget to check those out as well.

A lot of these questions will bring out some really funny answers, and some are just enjoyable to discuss. There are also some that might lead to an interesting deeper discussion but those are few and far between.

Feel free to cherry pick the ones you like or go through them like a list. Just remember that the point isn’t to ask all the questions, but rather it’s to have a great conversation!

List of fun questions to ask

Question 1: When did you screw everything up, but no one ever found out it was you?

What have you gotten away with? How sneaky were you when you were younger? Or was it something recent that you messed up and got away with?

Question 2: What would you name your boat if you had one?

The Unsinkable 3? The Cowboy Bebop? The Please don’t Sink? Your choice! Also, what would it look like? Do you want a motor yacht, a sailboat, or perhaps a dinghy?

Question 3: What will finally break the internet?

Take this question in a serious direction or a funny direction, either way it’s sure to get an interesting answer. Maybe even get a good conversation going.

Question 4: What celebrity would you rate as a perfect 10?

Great for guys or girls, see how your ideal type matches up with your friend’s. And if you are horrible with celebrity names like me, just think of a movie or show with a perfect 10 in it and IMDB it.

Question 5: Which fictional character would be the most boring to meet in real life?

Sure it’s easy to focus on the exciting, thrilling characters. But how about showing the boring ones some love!

Question 6: What is the best and worst purchases you’ve ever made?

Oh we’ve all made some seriously bad purchases, so what are yours? And what about the best purchase, and where can I get one?

Question 7: If you had to change your name, what would your new name be, and why would you choose that name?

So how about it? Will you be Inigo Montoya or Hubert Blaine Wolfeschlegelsteinhausenbergerdorff? Or perhaps something a bit more mainstream?

Question 8: What are some things that sound like compliments but are actually insults?

Along the lines of humble brags, but things that you would say to your frenemy. Sorry, as portmanteaus go, frenemy is almost as bad as phablet.

Question 9: What’s a body part that you wouldn’t mind losing?

You’ve got lots of body parts! Surely there a few you could part with. Who knows, maybe missing a few toes will become a fashion statement!

Question 10: What’s your biggest screw up in the kitchen?

Whether you did it when you were a kid or a as misguided college student, you’ve had a seriously bad screw up in the kitchen. So what happened?

Question 11: What’s the worst commercial you’ve recently seen? Why is it so bad?

It almost seems like some commercials were designed to be so irritating that you can’t forget them. So what are some of the worst?

Question 12: What’s the closest thing to real magic?

With a new “smart” something coming out almost every day, what products amaze and astound you the most?

Question 13: What is the craziest thing one of your teachers has done?

I’m sure we’ve all had that one teacher with a couple of screws loose, or how about the teacher that just absolutely lost it during class.

Question 14: Who is the messiest person you know?

If your answer is “I don’t know any really messy people”, that means that the answer is you. You are the messiest person you know.

Question 15: What problem or situation did TV / movies make you think would be common, but when you grew up you found out it wasn’t?

For me it was quicksand, always with the quick sand. That and the memory loss. I’ve never come across someone who had a complete memory loss or quicksand. Sure they exist, but they happen a lot more on TV than in real life.

Question 16: What quote or saying do people spout but is complete BS?

One that always gets me is “Love means never having to say you’re sorry.” You better occasionally say sorry, or there’s a good chance they aren’t going to love you for very long.

Question 17: What’s something your brain tries to make you do and you have to will yourself not to do it?

It could be as intense as the urge to jump off a high place. Or as mild as trying to stop yourself from itching that mosquito bite. Or maybe just saying something you shouldn’t at a really inopportune time.

Question 18: What is the dumbest way you’ve been injured?

Let’s face it, we’ve all had some injuries that were caused by less than dignified circumstances. So lets hear them! Everyone loves a good cringe worthy story.

Question 19: If you could know the absolute and total truth to one question, what question would you ask?

You can make it serious or funny, your choice. It’ll be interesting either way because we’ve all got plenty of questions we want answers to.

Question 20: What’s the most interesting thing you’ve read or seen this week?

Time to share that really cool article or fact that you ran across on the internet. Just make sure to fact check it!

Question 21: What ridiculous thing has someone tricked you into doing or believing?

We’ve all had our gullible moments, and everyone loves to hear about someone else’s embarrassment. So ask away and enjoy!

Question 22: If you were given a one-minute ad slot during the Super Bowl that you couldn’t sell, what would you fill it with?

Will you change the world? Annoy a lot of people? Inspire them? Or just use it as a platform to further your own diabolical plans?

Question 23: What’s the most useless talent you have?

You’ve got one, we’ve all got one. I’m pretty good at estimating what time it is, or maybe it’s just confirmation bias.

Question 24: What would be on the gag reel of your life?

Those moments when the audience that has been watching your life bursts out in laughter.

Question 25: Where is the worst smelling place you’ve been?

You know, that place where you gagged and almost threw up? Yeah that place!

Some other fun questions to ask!

Fun questions to ask a guy – More fun questions to ask! Some are just for guys, but many are for everyone.
Fun questions to ask a girl – Even more fun questions to ask! Wow, we really do have a lot on the site.
Would you rather questions – Always good for a fun hypothetical conversation. A great platform to jump off into a great conversation.
Questions to ask a guy – These are more general questions, but are really good and can lead to some really fun conversations.
Questions to ask a girl – Same here, they aren’t all girl specific and they are a lot of fun to ask and answer.