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

List of fun questions to ask

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!

1. What would you name your boat if you had one?

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

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Quiz: Which Friends character are you?

2. 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?

3. 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.

4. 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.

5. 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.

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6. 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.

7. Where is the worst smelling place you’ve been?

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

8. 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.

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!

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10. 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 let us hear them! Everyone loves a good cringe-worthy story.

11. 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!

12. What are the best and worst purchases you’ve ever made?

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

13. 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?

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14. 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 a phablet.

15. What’s your biggest screw up in the kitchen?

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

16. 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?

17. 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.

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18. 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?

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

I’ve never come across someone who had a complete memory loss or quicksand. Sure they exist, but it happens a lot more on TV than in real life.

20. What quote or saying do people spout but are complete bullshit?

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.

21. 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.

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22. 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.

23. What’s the most exciting thing you’ve read or seen this week?

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

24. 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 it!

25. 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?

Conversation Starters

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