Skip to main content

Last Updated on December 19, 2022

We can all agree that starting a conversation is not always easy, especially when the other party appears uninterested. If you’ve ever been found in a situation like this, you understand that the silence can be almost deafening. In that case, strange questions could just be what you need to break the ice, or in this case, the silence.

As funny as they might seem, weird questions allow you to get into the next person’s mind easily. It is a great way to strike up a light, casual conversation. Bizarre questions lighten the mood and provide a bit of comic relief.

Sure, they may make you appear crazy at first, but these unconventional questions can tell a lot about a person. These questions can also help you see things in a new light. The next time you want to lift the room’s spirits while getting to know the people present, and adding a bit of spice to the gathering, here are some weird questions to consider!

90 Weird Questions To Ask

  1. Which mythical creature do you want to become?
  2. What is the weirdest thing you posted on the internet?
  3. You discover a beautiful island upon which you may build your society. You make the rules. What is the first rule you put in place?
  4. What would you do if you found a dead body in a hotel room?
  5. If you have described something as indescribable, haven’t you already described it?
  6. Do you think if anything is possible, it’s still possible for anything to be impossible?
  7. Have you ever attempted to swallow toothpaste?
  8. Is it permissible for minors who act in R-rated films to see them?
  9. What’s your favorite pooping position?
  10.  Have you ever been tempted to sleep inside the fridge?
  11.  Is it a hostage situation if a person with several personalities threatens to kill himself?
  12.  Why is it called “taking a dump”? Shouldn’t it be leaving a dump instead?
  13.  Why do you think 11 isn’t pronounced onety-one?
  14.  Are we living or just slowly dying?
  15.  Why does rain drop but snow falls?
  16.  Can you describe the smell of your armpits?
  17.  Do fortune cookie predictions have a time limit?
  18.  When was the last time you screamed your lungs out?
  19.  If an orange is the color orange, why isn’t a lemon called a yellow or a lime called a green?
  20.  What is the longest time you have gone without showering?
  21.  If you’ll be expecting the unexpected, doesn’t that make the unexpected expected?
  22.  Isn’t it strange that rearranging the word “teacher” gives “cheater”?
  23.  How would anyone ever know if a word was misspelled in the dictionary?
  24.  Did you fail or succeed if you were trying to fail and you succeeded?
  25.  Would you believe a person who told you they were a pathological liar?
  26.  When it comes to movies and concerts, do conjoined twins pay for one or two tickets?
  27.  If corn oil is made from corn and vegetable oil is made from vegetables, where does baby oil come from?
  28.  Do you become a hater if you despise haters?
  29.  Will a teacher be “degraded” if they teach a younger grade than they previously taught?
  30.  Why did we choose to make February only have 28 days while so many other months have 31? Couldn’t we have added some of the 31st days from other months to February?
  31.  Which letter is silent in the word “scent”: S or C?
  32.  Which TV series would be most suitable for your life?
  33.  What weird or embarrassing thing can be found in your search history?
  34.  What was the most embarrassing “caught in 4K” moment?
  35.  What is worse during a kiss – a sneeze or a cough?
  36.  Can you make yourself seem like a psychopath by just one text? 
  37.  Name the wildest bet you’ve ever lost. 
  38.  What makes New Zealand new?
  39.  Why do we call cold things “chilled” while chillies are called hot?
  40.  If you were in a movie, what soundtrack would be in your fight scene?
  41.  Name a movie which changes its plot as soon as you change a letter in the title.
  42.  If a doctor has a heart attack during surgery, who will other doctors and nurses take care of first?
  43.  If a boy named after his dad is called junior, what do you call a girl named after her mom?
  44.  What’s the sickest you’ve ever been?
  45.  Who would show up at your funeral?
  46.  Would you rather know when you’re going to die or how you will die?
  47.  Whenever you ask someone “how they’ve been doing,” do you want them to tell you the truth?
  48.  Would you rather sit in the snow while it’s falling or dance in the rain?
  49.  Have you ever hurt someone just enough to make them scream when rendering first aid? On purpose?
  50.  Would you rather continue living for 100 years or restart your life from the beginning?
  51.  Would you rather be smacked in the face or smacked on the behind?
  52.  How would you dispose of a dead body if you only had an hour to get rid of it?
  53.  Have you ever killed anyone?
  54.  What is your favorite smell?
  55.  How many times do you lie in a day? Have you ever counted?
  56.  Do you think humans are less disciplined than animals?
  57.  What is the most disgusting food that you have ever experienced?
  58.  If animals could talk, which would be the rudest?
  59.  If you could be a fly on the wall, who would you want to listen in on?
  60.  Brushing your teeth or wiping your butt – you have to give one up. Which one would it be and why?
  61.  What’s the worst tagline you can think of for a brand that sells wart removal cream?
  62.  What’s something that doesn’t really smell great, but you keep wanting to smell it anyway?
  63.  What are three things you could buy at a grocery store to make the cashier give you weird looks?
  64.  What would you do after your boss fires you?
  65.  Would you rather be alive and alone or about to die with a group of friends?
  66.   Why is it called “beauty sleep” even though you wake up looking like a hot mess?
  67.  Why is sandwich meat round when bread is square?
  68.  Which would be the nicest if animals could only talk?
  69.  If you had the chance to invent a country, what would you name it?
  70.  What are two things that you think are normal but become strange when you repeatedly do them?
  71.  If you took out a ship and changed all of its parts until none of the original parts are intact anymore, is it still the same ship or a totally different one?
  72.  What’s the dumbest thing you’ve ever imagined?
  73.  What normal things do you think are sometimes not normal?
  74.  If you were a student at Hogwarts, which teacher would you rather have from the choices given?
  75.  When was the last time you stopped to smell flowers?
  76.  What ice cream flavor do you think best describes your life?
  77.  What’s the most embarrassing thing you have done while drunk?
  78.  Why does lemon juice have an artificial flavor while dishwashing liquid has real lemons?
  79.  Is your time truly wasted if you enjoy wasting it?
  80.  Why is it so difficult for women to apply mascara with closed mouths?
  81.  What sport would be the funniest to add a mandatory amount of alcohol to?
  82.  What would be your weapon of choice in a zombie apocalypse?
  83.  Where did the name Pina Colada come from?
  84.  If animals could talk, which would be the smartest?
  85.  Tell us about a weird and embarrassing thing that you’ve ever worn in a public place?
  86. What’s a weird thing that a neighbor has done in your front door?
  87.  Can you remember any real life person who looks like a famous fictional character that you enjoyed seeing being a kid?
  88.  Have you ever lied to a priest, preacher or holy man?
  89.  Have you ever dropped food on the floor and then picked it up to eat it?
  90.  Would you rather be a hero or a villain for a day?
Related:   40 Amazing Fundraising Ideas to Inject More Money Into Your Project


After answering these questions with anyone, a deep bond would undoubtedly form. It’s a subtle but entertaining way to see a person in a new light and connect with people in ways you never knew you could.  As Robert Fulghum once said: “We’re all a little weird. And life is a little weird. And when we find someone whose weirdness is compatible with ours, we join up with them and fall into mutually satisfying weirdness—and call it love—true love.” 

Sometimes getting in touch with your weird side and getting the chance to share it with others who are just as weird as you can be more fun than you think. Imagine thinking you were strange just for liking the sound of thunder only to discover that you’re not as unusual as you thought you were.  Exploring your strange side opens up a world of possibilities we may never have known about. And who knows what else? Your level of weirdness may be ideal for someone else. You might land the next big break or meet your life partner and best friend. Best of luck!