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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.

In this article, we’ll provide you with a list of fun questions to ask. You can use them as icebreakers, conversation starters, or just to add some fun to your interactions. If you’re interested in more fun questions, check out our other articles about great icebreakers and conversation starters! 🎉

Tips on how to have a fun conversation

Have you ever been in a conversation where you just can’t seem to find the right thing to say? You’re not alone. It can be tough to keep a conversation going, but with a few tips, you’ll be able to have fun conversations with anyone.

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Check out our tips on how to have a fun conversation, and you’ll be chatting up a storm in no time!

Tip 1: Show interest in the person you’re talking to

The best way to keep a conversation going is to show that you’re interested in the other person. Ask them questions about themselves, and really listen to the answers. People love talking about themselves, so this is a great way to get them to open up.

You can also share something about yourself in response to something they’ve said. This will help build a rapport and make the conversation more enjoyable for both of you.

Tip 2: Find common ground

Talk about shared interests, experiences, or even just observations about the world around you. For example, if you’re both dog lovers, you can chat about your furry friends. Or, if you’re both into the same music genre, you can discuss your favorite bands and songs.

Finding common ground will make the conversation flow more smoothly and help you connect with the other person on a deeper level.

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Tip 3: Ask open-ended questions

Open-ended questions are those that can’t be answered with a simple yes or no. They encourage the other person to elaborate on their thoughts, which can lead to a more interesting conversation.

Some examples of open-ended questions include:

  • What was the best trip you’ve ever been on?
  • What do you like to do for fun?
  • What would be your dream job?

Asking open-ended questions will help you learn more about the other person, and it’ll give them a chance to share their thoughts and feelings.

Tip 4: Avoid distractions like checking your phone

When you’re talking to someone, it’s important to give them your full attention. That means putting away your phone and any other distractions. Not only is it rude to be looking at your phone while someone is talking to you, but it also makes it difficult to really connect with the other person.

If you’re worried about missing a call or notification, explain to the person you’re talking to that you need to keep your phone close in case of an emergency. They’ll understand, and they’ll appreciate that you’re making an effort to focus on them.

📖 Suggested read: 70 Fun Questions to Ask Your Friends

Tip 5: Don’t try to be someone you’re not

It’s important to be yourself in a conversation. Don’t try to act like someone you’re not or say things that you think the other person wants to hear. This will only make the conversation awkward, and it’s likely that the other person will see right through you.

Just relax and be yourself, and laugh about yourself when appropriate. The other person will appreciate your authenticity, and you’ll both have a more enjoyable conversation.

Keep these tips in mind the next time you’re in a conversation, and you’ll be sure to have a good time. Who knows, you might even make a new friend in the process!

🤓 Suggest read: Tips on how to start a conversation

25 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?

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.

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 are a few you could part with. Who knows, maybe missing a few toes will become a fashion statement!

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?

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, a frenemy is almost as bad as a phablet.

👉 Suggested read: 200+ Interesting Questions to Ask a Girl

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

Whether you did it when you were a kid or as a 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.

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 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?

So there you have it – 25 fun questions to ask. We hope you’ll put them into practice and have some great conversations! If you want even more conversation starters, we’ve got a bunch of great questions for you: 👉 Check out this list of great questions to ask people!

Conversation Starters

Looking for some conversation starters and icebreakers? Check out our collection of articles full of tips, tricks, and ideas to help get the conversation flowing! Get to know how to talk to anyone anytime, anywhere!