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Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Dai ...
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by | | October 5, 2021


Some funny questions to ask friends are always handy to have for great conversation starters. And today, I'm sharing some really good ones.

I know the best questions to ask friends because I'm an expert when it comes to great questions to ask. Just check out some of the 150 articles I've written on the topic!

If you're ready, let’s jump right into it!

Contents

Ultimate List of Funny Questions To Ask Friends

Hanging out with friends is all sorts of fun! But you can sometimes be left with awkward silences if you're not fully prepared. And conversations are key and very important in any kind of relationship and it's what makes a hangout meaningful. You've undoubtedly heard it a thousand times, but that doesn't change the fact that it's true. Having a list of funny questions to ask your friends will make sure you are always ready to keep the conversations going.

Question Categories

6 Best Funny Questions To Ask Friends When Bored

You can have some of the best conversations with friends on the most random of topics. Forget questions like, "who is your favorite celebrity crush?" Turn a boring discussion into a sidesplitting exchange with these amusing questions that are sure to start some colorful dialogue.

Here are 6 funny questions to ask friends when bored:

1. If you could shoot one condiment from your belly button, what would it be and why?

Undoubtedly a surprised chuckle or snort may be the first response. But this is probably the first time they've ever had to think of this scenario. Give them a moment to think of their answer.

2. What is the best excuse for being late you’ve heard or used?

Take note because their answer could come in handy someday. There is often an interesting story behind these, so make sure they expand and expose all the deets.

3. Why do some people go to the refrigerator again and again with hopes that something new to eat will have suddenly appeared?

A philosophical question to trigger some creative thinking. These types of discussions are insightful and entertaining.

4. If you had to eat a crayon out of its box, what color would it be?

Forget boring small talk. Crazy topics are what it's all about. This funny question is a fantastic ice breaker and is sure to get someone's attention.

5. What ridiculous and untrue, yet slightly plausible, theories can you come up with for the cause of common ailments like headaches or cavities?

As no headache or ailment is ever the same, this is sure to spark some deeper talks. It's amusing to see what abstract answers people will come up with sometimes. If you have someone with a medical background join this conversation, it may become even more fun.

6. If you were a transformer, would you need a car or life insurance?

Transformers are living, human-like robots that can transform into vehicles or mechanical beasts. A debate over what insurance it should have can stretch into a long conversation and open a world of similar controversial polls. You may need someone to decide the winner.

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6 Funny Yet Interesting Questions to Ask Friends During A Sleepover

Keep the sleepover alive and everyone awake with interesting conversation topics. Don't struggle with dull moments when you have friends over and be ready with funny questions to ask your friends. When you ask these interesting questions before you know it, the sun is up, and it's already morning.

Here are 6 funny yet interesting questions to ask friends during a sleepover:

7. What would some fairytales be like if they took place in the present and included modern technology and culture?

There are already modern adaptions of fairytales gracing our screens, but this does start a conversation to share some creative ideas. Who knows, you may discuss an idea so great it turns into the next big Netflix hit!

8. Milk before cereals, or cereals before milk?

An alternative riddle to, "Who came first, the chicken or the egg?" Except in this discussion, there is no scientific argument, but more personal opinion and habit.

9. Would you eat a person if you really had to?

Cannibalism is always an interesting topic because it often becomes a moral debate. You can also learn a lot about someone's character based on their survival instinct and just how far they're willing to go.

10. If a strand of spaghetti accidentally went out of your nose, would you sniff it back or pull it out with your fingers?

You may learn their gag reflex with this one, or it may be met with a snort. Either way, it's definitely not one of your standard questions.

11. Is a hotdog a sandwich?

Or if you put a hotdog sausage onto a piece of bread, does it become a hotdog? This sets in motion another debatable discussion.

12. What kind of cult would you like to start?

A cult is a system of reverence and devotion to a particular figure or item. A talk about cults is bound to trigger some unique and surprising answers.

6 Funny Conversation Starters To Ask Your Best Friend

Throw a curveball and make an impression with funny conversation starters! Excite some laughs and joyous moments with these questions to ask your best friend. Do you know them well? Maybe they'll shock and amaze you.

Here are 6 funny conversation starters to ask your best friend:

13. If I turned into a zombie, would you try to keep me around in case a cure appears, or kill me straight away?

If you don't like what your bestie decides with this one, perhaps now is an excellent time to have that conversation and make plans for the what-ifs. Have you discussed preparedness 101 in the event of a zombie apocalypse? Now's your chance.

14. Can I see your browser history?

Unless they clear their browsing history on a regular basis, you may find some juicy and hilarious searches. Some of these can be pretty private and embarrassing too.

15. Why do you say that we have the weight of the world on our shoulders, but when we try to express it, we say we have to get it off of our chests?

Ah, the beauty and complexity of the English language. Thought-provoking, interesting questions like these may actually frustrate them because it can be hard to articulate a meaningful answer. Or, it could be met with awkward silence.

16. What’s the worst date you've been on?

Some experiences can be written down for a scene for a great comedic novel because just as facts can be stranger than fiction, real people can be worse than a fictional character! Comparing worse dates might make you cringe, but they're fun to talk about.

17. What is the worst fashion decision you've ever made? Do you have a picture of it?

A fun question and possibly a fun reveal. When photos are brought out, you know the topic can go on and on. Photos wearing a ridiculous outfit isn't necessarily the worst thing. Right?

18. Do you think cavemen had nightmares about cavewomen?

Stupid questions are a dime a dozen, but they can initiate some comical answers. When your friends are willing to answer these, it can be a riot of a discussion. Do they offer you witty answers or something with some actual thought put behind it?

6 Crazy Questions To Ask A New Friend That Are Too Funny To Ask

Making a good impression and building a solid foundation in new friendships is important. Initiating small talk can be challenging, so early on you should be prepared. You need to know the best questions to ask a new friend to get to know them better and avoid getting caught out with nothing to talk about but the weather.

Here are 6 crazy questions to ask a new friend:

19. If you had to choose between going naked or having your thoughts appear in thought bubbles above your head for everyone to read, which would you choose?

Either of these could be someone's biggest fear if it were ever to happen. Think about what thoughts run through your head and imagine this happening. Or walking down the street in your birthday suit. These are not a fun way to be... revealed.

20. Do you think we were destined to meet and be friends?

It is a good question to ask. Whether they believe in destiny can say a lot about a person. And whether they think you were meant to meet and become friends says a lot about the current state of your relationship.

21. How would you show that you were from the future if you were transported 200 years into the past with no clothing or anything else?

A weird question is sure to also act as an icebreaker question. But with some deep thinking, this can open up a deep and intriguing discussion.

22. Have you ever taken a personality test?

Millions of people take personality tests each year, and often if they have, they enjoy talking about the results. A random question like this can turn an acquaintance into a close pal because there is so much you can discover about each other. If they've taken the Myers-Briggs test or any other, they'll likely have a comment or two about it.

23. Do you think about having a remote control home where you just have to speak things like ice cream come here?

Isn't this where the world is headed? With the advancement of technology, ice cream may one day respond with a mere command. Talking about all the possibilities can have you talking for hours.

24. What's your favorite sleeping position?

Nothing like a personal question to strengthen a connection. Asking about sleeping habits may seem odd after just meeting, but they can't say you hold dull conversations.

6 Funny Most Likely To Questions to Ask Friends

These funny random questions can play out like a game. Most Likely To questions are similar to fun trivia but no answer is wrong. They are super revealing about your mates' opinion of the people in your circle. If you're trying to liven things up, create a bit of a gaming vibe into your discussions, then these are perfect.

Here are 6 funny most likely questions to ask friends:

25. Who is most likely to leave movie spoilers, online?

There is a buddy that spoils movies or series for everyone. Whether it's a slip of the tongue, a review on their Instagram story, or an outright rant post about what just happened not realizing no one else has seen it; there is always someone. Or perhaps it's you that's spoilt your own favorite movie for someone?

26. Who is most likely to get drunk and pass out at a party?

The craziest thing about this one is there is usually a rebuttal from the person chosen, then a sudden realization that the opinion is probably right as examples of their escapades are shared.

27. Who is most likely to have a heart attack from watching a scary movie?

A terrifying movie may actually be someone's guilty pleasure, but usually, there is someone that can't watch even two minutes before goosebumps start forming on their skin.

28. Who is most likely to be the worst at singing?

As someone is pointed out, an apology might also be made. If they disagree, perhaps have them sing their favorite song.

29. Who is most likely to dance in public?

The funniest thing is they'll either cringe and deny it or be proud as hell! Dance is an art. If you've got the moves, why not show it off right?

30. Who is most likely to eat in a restaurant without paying the bill?

A girl will blush, and a guy will smirk. An explanation and justification for the choice may be needed.

6 Funny Would You Rather Questions To Ask Friends

Would You Rather Questions are fantastic conversational aids. It's engaging to play and priceless to see some reactions to these comedy questions. It doesn't matter if you're not at your favorite place, or it's not your favorite season, feel like a kid again and have a great time asking these.

Here are 6 funny would you rather questions to ask friends:

31. Would you rather have hands that kept growing as you got older or feet that kept growing as you got older?

Did you know your hands and feet stop growing first? It would be interesting to know how much bigger they may have gotten if they stopped growing last during our development stage. You might have ended up looking like a cartoon character!

32. Would you rather take an ice-cold shower and be clean or not shower at all?

Well, this may depend on where you live and what the current season is. If you were in the desert, this might be your favorite thing. Cold showers have been proven to have some unique benefits, however. They are also suitable for calming itchy skin, and we all know they're excellent at waking you up.

33. Would you rather be compelled to high-five everyone you meet or be compelled to give a flying kiss to anyone in a green shirt?

It's a great question that makes you stop and think. What would be the best option here?

34. Would you rather be forced to eat only spicy food or only incredibly bland food?

If your favorite food happens to be spicy, then this won't be hard to answer at all.

35. Would you rather have no eyebrows or only one eyebrow?

As eyebrows have an essential role on the face, one eyebrow may be better than none. Aside from them making us look great, eyebrows have the purpose of stopping sweat or moisture from getting into our eyes. It might look like the weirdest thing, so it's really your choice.

36. Would you rather be born with an elephant trunk or a giraffe neck?

For the Kayan tribe of Myanmar, long necks are a standard for beauty. A giraffe neck, however, might be a little too long though. But indeed, having an elephant trunk couldn't be much better. Regardless of what is chosen, this is a fascinating conversation starter.

6 Funny Questions to Ask Friends During A Never Have I Ever Game

If you're looking for a way to refresh a dull discussion, Never Have I Ever questions are the perfect go-to. Don't ask dumb questions. Level up your next group chat or get together with these random funny questions, and savor the crazy enjoyment. You might also learn a thing or two about each other.

Here are 6 funny questions to ask friends during never have I ever game:

37. Never have I ever used a fake ID.

Whipping up something juicy to start offsets the standard for the rest of the game. But it's still good to mix in some mundane things to spark the shocking ones.

38. Never have I ever kissed someone in public.

The best thing about this game is every time something is asked, it has the potential to trigger a fantastic anecdote.

39. Never have I ever crashed a wedding.

You've definitely advanced from asking things like, "what's your favorite color?" Make sure if someone does say they've done this, get the full story.

40. Never have I ever lied to my best friend about who I was with.

This may expose the biggest lie, so be prepared.

41. Never have I ever climbed out of a window.

It may seem like everyone has done this at least once. Yet perhaps not everyone has ever found a need to escape or exit from something other than a door.

42. Never have I ever yawned on a date.

If you have, perhaps looking at some quality first date questions is just what you need! Throw some flirty questions, and you won't be yawning on your date again.

5 Funny Quotes About Friendship Everyone Can Relate

There are many quotes about friendships, and while some teach valuable lessons, others can be used to start more profound talks. Quotes aren't always just something you screenshot and have hundreds of in your phone gallery; they're useful for sharing opinions and debating their meaning.

Here are 5 funny quotes about friendship:

"A true friend stabs you in the front". – Oscar Wilde

Even when it hurts, true friends will be completely honest. They'll tell you straight up, and usually for your own good.

"I don’t like to commit myself about heaven and hell — you see, I have friends in both places." — Mark Twain

As no two persons are the same, our friends come to us with a variety of personalities. Some will encourage us to do good, and some will encourage us to do... bad. Like, climb out a window at night to escape our curfews!

"If you can survive 11 days in cramped quarters with a friend and come out laughing, your friendship is the real deal." — Oprah Winfrey

Being stuck in cramped quarters with anyone is sure to push some limits. We love our friends, but sometimes too much time with them can be, well, too much. Space is good for any relationship.

"A true friend is someone who thinks that you are a good egg even though he knows that you are slightly cracked". – Bernard Meltzer

The past that shaped us and our flaws don't matter to true friends, for they accept us for who we are.

"Some people go to priests; others to poetry; I to my friends." — Virginia Woolf

Our friends often become our saving grace and offer us comfort and reassurance when we need them. That is why friendships are so powerful and necessary for our mental wellbeing.

Downloadable And Printable List of Funny Questions To Ask Friends

Here is a downloadable and printable jpg/pdf list of Funny Questions To Ask Friends (right-click the image and select Save Image As...):

Frequently Asked Questions

Communication is an integral part of daily life. Some people are great at it; others find it difficult. While this list provides you with what you need to enjoy your time with your friends, it may have proved questions of your own. So, check out our FAQs.

Is it okay to ask these questions to my shy friends?

Answering many questions, especially if they are considered personal, can feel exhausting for your shy friends. The questions here are all suitable as they're meant to be funny and help start conversations.

Are these questions appropriate to ask in any situation?

As always, read the room. In other words, no, because it depends on the situation. If you were at a funeral, you wouldn't want to be asking funny questions like these as it would seem rather inappropriate.

However, if someone were sad, you may break one out to get them to smile. You can also try your funniest joke. These questions are the best funny questions to ask friends when bored.

What questions should I ask over text? Is it still funny when asked through text?

All of these are definitely good over text. They hold their hilarity as well. Make sure to reply with a funny answer if they ask you similar questions too. And if you want to keep it going, make sure to ask an open-ended question.

How do I know that my questions make my friend uncomfortable?

Usually, their facial expression or body language will tell you. Otherwise, you can always ask. Not everyone likes opening up about their biggest pet peeve or is happy to discuss their opinions of the weirdest smell, and that's okay.

You can try another one, or hopefully, they ask you some to know what kind they're comfortable with.

Why it's important to ask questions?

Well, to get answers, of course. Asking questions can help you understand challenges and problems. They're essential for proper communication. Asking questions to your acquaintances, friends, and family enables you to understand them better. Answers to the questions asked can tell you a lot about someone.

How To Make Any Conversation With Your Friends Light And Better

To have better conversations with your friends, there are some simple steps you can take.

Here's how to make any conversation with your friends light and better:

1. Slow down and don't move on so quickly.

Often we can get excited in our thoughts and want to jump onto the next topic quickly. Don't. Make sure to listen and move the discussion at a natural progression.

2. Make sure to share as well.

Conversations are about you sharing as well. It's an exchange, so ask questions, listen, and share.

3. Give verbal nods and gestures.

This is when you say things like "ah-ha" or other subtle gestures letting your friends know you're following along to what they're telling you.

4. Seed deeper topics.

Simple questions can do this. Seeding topics are about introducing new things to talk about without forcing it, like commenting or adding on an anecdote, then branching off from there.

5. Show a bit of modesty.

Don't overdo it with the "I'm so great" stories. You have more effortless flowing conversations when the discussion isn't always about you.

More Awesome Questions

Try mixing things up sometimes to make more memorable moments and have better, more meaningful conversations. Here are some great suggestions:

  1. Trivia is all sorts of fun, but coming up with some great questions can take a lot of energy. Luckily we've compiled the best Funny Trivia Questions for you already!
  2. If you're ever in a situation where strangers surround you and need to come up with something to do quickly, Fun Ice Breaker Games are the answer.
  3. Having an enjoyable time with your friends is important, but having deep and meaningful conversations is needed too. Try our Deep Questions To Ask Friends to reinforce your connection.

In Conclusion

Young or old, it's good to know some funny questions to ask friends. You won't find better comedy questions, stupid questions, dumb questions, or funny questions to ask your friends than the ones here.

Always be ready with questions to ask friends to use as great conversation starters!

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