51 Crazy Questions to Ask Someone

If you need crazy questions to ask someone, you are in the right place. These questions will surely spark lighthearted conversation, whether you are old friends or simply meeting for the first time.

Asking these questions will help you know how to relate to them and help them feel at ease. Be wary, though; any of the offbeat queries you pose could provoke an equally offbeat response. 

Photo by Brett Jordan on Unsplash

Fun Random Questions to Ask Someone

Asking funny questions can help you reveal someone’s unique personality. These prompt questions people to think about who they are and why they are like they are. 

  • Do hairnets have to be worn by bald waiters? 
  • Would you rather be blind but have a friendly smile, or have no nose but good-smelling fingers? 
  • Isn’t it the case that you’ve already described something if you call it “indescribable?” 
  • In retrospect, what clothing item did you find most humiliating to wear? 
  • How many pennies could you fit in here? 
  • What’s the funnier of the two questions?

Hot Interesting Questions to Ask Someone

We can use hot seat questions for basic in-depth conversations. It could be abstract, benign, personal, and a fantastic conversation starter.

  • Once you enter a room, what song(s) would you want to hear? 
  • Can you tell if a fish is thirsty by looking at it? 
  • Does one’s IQ have a ceiling? 
  • Give us the lowdown on the worst job you ever held. 
  • When did you last watch a television program? 
  • Which of your past actions do you most regret? 
  • Where on Earth would you choose to settle down if money were no object? 
  • To which members of your family do you look up to as if they were your best friends?

Most Embarrassing Questions to Ask Someone

Skinny questions do not require much thought to answer, or it cuts right to the point. They are designed to get to know people and are generally fun and intriguing questions.

  • To what extent have you borrowed something and failed to give it back? 
  • If you were a Martian, how would you approach a problem? 
  • Please name two things that seem commonplace at first but start to feel odd after you’ve done them a few times. 
  • Do you agree that true creativity requires you to invest emotionally in your projects? 
  • How has your background informed your professional path? 
  • When you create something, do you want it to be original?

Creative Questions to Ask Someone

You can ask creative deep questions to provoke a mental conversation that can lead to novel conclusions and discoveries. Inquiries open up a vast potential for fresh insights and innovative ideas. 

  • What does the DMV put down as your hair color if you’re bald? 
  • Exactly how do birds urinate? 
  • What is your favorite TV show?
  • Is it possible that one day humans will live forever?
  • You’ve found a stunning island where you can establish your civilization and write the rules. What will be the first regulation that you institute?
  • What gives you the impression that everyone who drives faster than you is an idiot? And that those who are faster than you are morons?
  • Considering it’s a friendly fire, why aren’t they covering up?
  • How many chickens would it take to slaughter an elephant? 
  • Have you ever rewrapped a present given to you?

10 Deep Crazy Questions to Ask Someone

These questions are guaranteed to make you pause before responding. They are simple but reveal a lot about a person’s character.

  • Why do some types of lemon juice have an artificial flavor while others, like dishwashing liquid, actually use real lemons?
  • To what extent can you tell someone about yourself? 
  • Should I also count my eyebrows as facial hair?
  •  What is your preferred squatting posture? 
  • What’s on your bucket list?
  • How likely would you consider spending the night in a refrigerator? 
  • In which celebrity’s face would you most like to land a punch? 
  • In other words, what are you hoping to accomplish before you die?

Wrapping Up

Finding crazy questions to ask someone can be challenging, but some questions always work. They don’t have to be deep, funny, or tricky questions. The questions give an insight into the person sitting across from you that you would never be able to find otherwise.

Abir is a data analyst and researcher. Among her interests are artificial intelligence, machine learning, and natural language processing. As a humanitarian and educator, she actively supports women in tech and promotes diversity.

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