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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 Jasper | August 19th, 2021
via: Unsplash / Omar Lopez
Funny questions to ask are perfect for starting a conversation but we get it...
Starting a conversation can be tough. Sometimes you can't think of any questions to ask and every time you try to keep things moving, the conversation fizzles and you're left awkwardly looking at your surroundings.
Maybe you're dealing with some anxiety or maybe you simply can't seem to find a way to connect with the person you're talking to.
Good news. Humor is your friend!
Everyone loves to laugh and doing so has a number of benefits, including making us feel more comfortable when we're nervous. And even if you're not known as "the funny guy", if you keep a few of these funny questions to ask up in that noggin of yours (or even whip this article out when you're with company), you'll always have something hilarious to say.
via: Unsplash / Jared Sluyter
Before you talk to someone, you have to know what you're going to talk about. So you'll need some conversation topics, which should be relatable enough that anyone can say something about them. Depending on where you want the conversation to go, there are countless conversation topics to choose from, from the basic getting to know you questions to the existential.
But you're here to be funny. So here are conversation topics to get your mind geared towards the silly and ridiculous. In general, you're going to have more success with these questions if you have your own story to share.
Here are the 10 best funny conversation topics:
PSA: Never put water on a grease fire. Here's why. And another example.
via: Pexels / Creative Vix
Well this is embarrassing...
Maybe that dream where you forget to put on pants actually happened to someone.
Exaggeration is key when demonstrating. The more ridiculous you look, the better.
If he/she doesn't want to share it, you'll have to share something first.
GoT spoiler alert: The Boltons are dead, thank goodness.
via: Unsplash / Phil Shaw
You could shrink an encyclopedia and be the coolest kid in town.
Everyone has to wear their underwear on their head.
Christmas + Thanksgiving + Halloween + New Years = One great party.
Matted hair or funky breath? Hmmm.
via: Unsplash / Priscilla Du Preez
You're not going to start a conversation without conversation starters and using funny conversation starters is a perfect way to get the ball rolling.
They open up the conversation to new topics and will make your conversational partner more comfortable knowing that he/she doesn't have to think up new things to talk about (especially if he/she has social anxiety). Plus, everyone loves a guy who can make them laugh!
Here are 15 best funny conversation starters:
Some dirty, stinky sneakers or the loveliest pair of high heels?
Elves were high society. On the other hand, six meals and walking around New Zealand barefoot would be pretty cool.
Streakers bring fans together. Would you be willing to face the consequence for the greater good?
This one will never fail to bring about a good story.
I've always wanted magic pants. Whenever I need something, I could just pull it out of my magic pants pockets.
via: Unsplash / Eaters Collective
I choose sandwiches. The possibilities are endless, really.
One of my favorite Black Mirror episodes touches on this.
Chainsaws? You'd never be able to pet puppies again...
Someone has to repopulate the earth. Might as well be you.
I love lamps.
via: Unsplash / Jasovsky
This one for me. Every time.
Lots of establishments have pictures of employees on their walls. Take the cashier's picture from the wall, go home and make a bunch of copies, return to the store and put those copies in a handful of picture frames, then buy those picture frames. That should do it.
This works best if you say it completely out of the blue.
You could go on and on with this one.
Some are more dangerous than others. What would the impact be?
via: Unsplash / Rhett Wesley
via: Unsplash / Giorgio Trovato
Ice breaker questions help people feel more socially connected and comfortable revealing more of themselves to make the best of everyone's time together. Ice breaker games take the former one step further and get everyone up and moving.
Here are 10 funny ice breaker questions:
Honeybadger, anyone?
The internet is many things, positive and negative. This might be a singular gauge for modern optimism and pessimism.
via: Pexels / Matthias Cooper
Grass is great. What other infinite, soft, inviting surfaces can your new friends conjure up?
There were centaurs. Mermaids. Duck-billed platypuses. It's all fair game for a new creation.
This could be a secret or something like your nail clipper.
Hack, hacking away at life.
Cat memes for rainy days or maybe their mind goes the more practical, survivalist route. Maybe they go the pampering route. Sushi for miles?
via: Unsplash / Tim Mossholder
There's nothing funnier than a cursing parrot. Because it makes us realize that curses aren't necessarily bad words if everyone's laughing and more at ease upon their uses.
What sort of image would you choose to hide the real you?
via: Unsplash / Rafael Leão
Would you rather questions are ridiculously fun to ask. They're perfect for delving into your conversational partner's mind and steering the conversation into a more absurd and hilarious direction.
They basically boil down to asking, "Would you rather [option A] or [option B]?"
I've never found a question that fails to make me laugh but our post on funny would you rather questions is another great resource to enhance any conversation.
Here are the best 14 funny would you rather questions:
Do you prefer crunchy or chewy? You might have options, depending on the rules.
Always carry a can of Prego in either scenario.
You're going to smell a stink either way.
A tough choice if you have a busy mind.
via: Pexels / Rene Asmussen
Parties every night or constant prying?
Bundle up or take it all off?
Both would be absolutely terrible.
Would you rather have sunglasses or shirts be obsolete?
Annoy everyone by shouting or be annoyed that no one can hear you.
via: Unsplash / Ben White
This one made my blood boil.
Whatever you choose, at least you'll have a protein-rich breakfast every morning.
Either can be trendy if you're hip enough.
Your doodles in class won't doodle themselves but you could be a legend among your classmates if you're not afraid to boogie.
Who's a good boy?
via: Pexels / Kat Jayne
via: Pexels / Elle Hughes
So there's a girl you like. She's cool, she's great, she could be the one.
Do you have any questions to ask a girl up in that brain of yours? You should. Otherwise you'll be sitting across from each other, looking at the decor of the restaurant you couldn't actually afford to take her to.
And funny questions to ask a girl are hilarious and bound to keep her interested.
Here are the best 14 funny questions to ask a girl:
The only time this could backfire is if she doesn't have a sense of humor.
It's a funny way to seal the deal if you know if a girl likes you.
Use your hands to smush your face together for a giggle.
Young and wild and free.
via: Unsplash / Tommaso Fornoni
Ghost story or odd encounter with a stranger?
And everyone pretended they didn't hear you. Spooky.
Because that's what's for dinner.
Use your imagination!
The little people are mining your teeth for Fluoride so they can power their homes in your nasal cavity.
via: Unsplash / Carolina Heza
Turn the friggin frogs gay.
If she knows Capoeira, she won't have to worry about it.
Food spoils.
Come here, boy!
I have a friend who is in her twenties and likes middle-aged men. You like what you like.
via: Pexels / Katii Bishop
via: Pexels / nappy
Every so often you meet a guy and you have to talk to him. Maybe you're on a double date and your girlfriend really wants you to get to know her best friend's new boyfriend or maybe you're in a study group and don't have any prepared questions to ask a guy but your entire group is comprised of guys.
No need to worry. We're all a bunch of boys at heart and just want to have a good time.
Here are the 13 best funny questions to ask a guy:
Don't worry, I'm not going to Rickroll you again.
Wait, what does the fox say again?
Every guy needs an animal sidekick.
We've all had at least one.
via: Pexels / Anete Lusina
Eyeliner really brings out your eyes and makes you look like Khal Drogo. Hot pink nails will show your manly side.
He's a talented artist but a little full of himself. Case and point.
Would you name your kid after a cardinal direction?
He might have some pointers for you.
We've all thought about how we're going to handle a zombie apocalypse.
via: Pexels / Skitterphoto
Depending on the dream, it could still be possible!
Again, we're all boys at heart.
Happy Purge day! Lock your doors!
But avoid these places.
via: Pexels / Gustavo Fring
You got a girlfriend. Nice work but slacking will ruin your relationship. If you stop trying as hard to make her happy as you did in the beginning, you're only going to push her away.
Remember to constantly surprise her, shower her with affection, and carry a list of questions to ask your girlfriend that you can pull out to keep her on her toes.
Here are 8 funny questions to ask your girlfriend:
Oh, baby.
If she can't think of any, ask her parents.
Devil worms are so hot right now.
Can you return groceries?
With great power comes great responsibility.
via: Unsplash / felipe pelaquim
And please say yes.
Seems like there's a good test for this.
Metallic isn't it?
You know what they say about big feet, don't you?
via: Pexels / cottonbro
Random encounters happen if you're social. Because I'm a writer now, I don't go outside anymore so I've almost forgotten what that's like to actually talk to people.
But you're a socialite and are constantly surrounded by interesting people and therefore have all the get to know you questions memorized, right? You might even have a few funny get to know you questions up your sleeve. More power to you!
Here are 8 funny get to know you questions:
Well stop masturbating with other people in the house.
Do they choose speed or style?
Can we go to Italy?
Why do I need to use scissors to open my scissors?
They used to be so big you couldn't carry one in your pocket.
via: Pexels / Andrea Piacquadio
I'd visit Curiosity on Mars. I'm sure he's lonely.
You don't put a playground right next to a bar. It's entrapment!
Some people like to live life on the edge.
via: Unsplash / AllGo - An App For Plus Size People
Make your new friend laugh with questions that you wouldn't even think of in a normal conversation. If you're looking for funny questions to ask a new friend, then you're in luck. The fun part is, the crazier the answer, the better.
Here are 8 funny questions to ask a new friend:
How would they know if they're asleep?
Hopefully, not Cruella de Vil or something...
via: Unsplash / Rod Long
Just promise to keep it between the two of you.
Wouldn't hurt to know. *saves password*
I bet they'll suddenly try to do it when you ask this question.
Good looks and charms are part of the options!
By the time you find out what, you're probably too late. There's no turning back now.
via: Pexels / Rodolfo Quirós
It would be interesting to know whether they describe it in a way that would make the aliens turn back or stay.
via: Unsplash / Antonio DiCaterina
What good are truth or dare questions if you don't have some dares to back them up? These funny dares will have the whole room roaring with laughter. Funny dares keep the mood upbeat, even if someone just dropped a hard truth in the last round.
Sure, doing a funny dare can be embarrassing, but that's all part of what makes the classic game of truth or dare such a good time. And, embarrassment isn't always a bad thing. Temporary shame can create bonds that last a lifetime.
If you're nervous about a dare, just think about the big picture. Shame lasts but a moment, but legends go on forever. Sometimes acting a fool is the best way to mark time and create memories.
Here are 6 funny dares for truth or dare:
Close your eyes and go for it.
And then wash out your mouth with soap.
What's worse – knowing what's in it, or not knowing what's in it?
What's the big deal? I mean, it grows back, right?
via: Unsplash / Michael DeMoya
Make sure you end it on a high note.
Audience interaction is a must for any good belly dancing performance.
via: Unsplash / Mike Erskine
Occasionally you'll run into a person who seems to have it all figured out. Because he/she is so interesting, you have a ton of deep questions to ask but you want to be witty.
When your conversation takes this route, don't panic. Sure, you might have to think about things like you've never thought about them before, but you'll learn quite a bit about yourself and more importantly, the person you're talking to. Everyone has a new viewpoint to offer and asking deep questions is the best way to discover a new way of looking at things. Being funny about it doesn't hurt either.
Finding perspective will help you grow as a man.
So when you find yourself in a situation like this, use these 8 best funny, but deep questions to ask and you'll be excited with where they take you. They'll keep the conversation very interesting but also lighthearted and fun.
Here are 8 best funny, but deep questions to ask:
In the present day, there are two schools of thought. You love him or hate him.
Dazed and Confused? Lost in Translation? Spy Kids 2?
It's a fun game to pass the time.
via: Unsplash / Matthew LeJune
Even if you don't believe in ghosts, ghost hunting can be exhilarating and educational.
Be careful. Time travel is dangerous.
Do you have a bug out bag?
Because I find you unbearable. *Wink*
Wedgies? Passive-aggressive comments? Try ignoring them.
via: Unsplash / bantersnaps
via: Unsplash / You X Ventures
After asking or answering tons of interview questions, everyone is looking for a laugh. Common ground. Sense of humor says everything about how much a person is holding back, how much they feel pressured to conform, how much they could be hiding.
Some funny interview questions could also help a shy, nervous candidate get their footing too.
Here are 7 funny interview questions:
You're asking the candidate to quickly come up with a world that's drastically in contrast to the human world, and playoff both of them. This sounds like a silly, vapid question, but it's actually drawing out a person's awareness of cultures beyond their own. Ask it!
This one is out of left field, and you're testing your candidate's courage to respond from a place far outside the box.
A healthy love and passion for animals is always a boon.
The more important part here would be why money is something other than green.
How willing is the candidate to use their senses beyond seeing and hearing and imagine how others might be operating from them as well.
via: Unsplash / Dmitry Mishin
People show their true colors when they're a bit caught off guard. If you start seeing your candidate bristle and get defensive and snotty at the randomness of your questions, you can infer that he might not be willing to dive deeply and fully into the unexpected demands of living and working in this day and age.
This is a pure test of gratitude recognition. Does the candidate recognize what is good and blessed in their lives? This is an optimum gauge for positivity.
How does the candidate interpret the needs for speed, stealth, and absolution in this situation, and in all other less-deadly, more daily situations?
via: Unsplash / Quaid Lagan
After reading this article, hopefully you've learned how to start a conversation and how to get to know someone by being funny. Here are 6 tips to ensure you get a laugh.
Here is how to ask funny questions:
Confidence is key when being funny. If you believe your corny jokes are funny, so will everyone else. Unless they're not funny.
A funny question is only funny in and of itself. Add more to it by cracking stupid jokes.
via: Unsplash / Brooke Cagle
After you ask a funny question or tell a joke, shoot a sly grin or wink towards the person you're talking to so they know you're joking.
You may think of some dad jokes. Blurt them out! Being funny requires pushing the envelope.
Timing is one of the most important aspects of being funny. If your timing is off, your jokes fall flat. Watch some comedians for pointers.
via: Unsplash / Mattheus Ferrero
These questions are supposed to make things easier for everyone involved! So relax and enjoy yourself! You've got this.
Here is a downloadable and printable list of funny questions to ask (right click the image and select Save Image As...):
via: Mantelligence
Feeling funny yet? Hopefully these funny questions to ask will be the building blocks that will lead you to countless hilarious conversations.
Maybe you're still nervous. That's okay.
Just remember the tips, pay attention to funny people and learn their methods, and allow your thoughts to flow into the absurd and you'll surprise yourself with just how much you can make people laugh with the right questions to ask.
One of the greatest discoveries a man makes, one of his great surprises, is to find he can do what he was afraid he couldn’t do.
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