Weird Questions to Ask People

Updated on February 4, 2018
ControlledChaos1 profile image

I have many interests and an inability to make up my mind about which one to focus on. That's how I came up with my name: ControlledChaos1.


If you want to give someone a memorable experience, then ask them a weird question. Sometimes you'll be lucky enough that they'll not only decide to answer, but begin a great discussion between the two of you to make you both have a memorable experience.

I've never understood the mundane questions most people use for chit-chat to pass the time. Who cares about the weather, when you could be talking about something that makes both people think and wonder. Of course, to ask (or answer) such questions, you need to have a few of them on your mind. That's what this article is all about. I look forward to hearing one of these wonderfully strange questions being asked to me by a complete stranger sitting on a bench. In fact, you may have already met me, because I do ask these kinds of odd questions whenever I get the chance. Almost all of my personal experiences have resulted in amazingly weird conversations and friendships.

Below you'll find some questions (many of them uncomfortable) that you can actually answer due to the fact that people can answer them without anybody ever knowing who they are. A rare opportunity for sure. Hope you enjoy!

Have you ever had an imaginary friend?

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Be Prepared For The Answer Before Asking The Question

Have you ever killed anyone?

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I realize the question above is controversial. Most people who say yes will be likely military, police or someone defending themselves. There is also a distinct possibility that anyone who answers it can be totally lying, but think about this... they could also be telling the truth.

If you ever ask a person this type of question in person you need to make sure you know them well enough to know that they won't hurt you if they say yes.

Asking Embarrassing Questions

It's No Fun When You're Forced To Tell The Truth

Would you ever take a lie detector test with a loved one asking the questions? (best to answer this one when you're alone).

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Can I Go To Hogwarts?

If you were a student at Hogwarts, which teacher would you rather have from the choices given?

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Five Minute Rule!

Have you ever dropped food on the floor and then picked it up and eat it?

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A Touchy Subject

Still a virgin?

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Strange Or Interesting Interview Questions

Interview or application questions are tricky; you don't want to ask questions with the intent of finding out how smart (or not) someone is. Your goal should be to find out if this person can help your business. One more tip to employers is to not get mad or rule people out of a job when they are honest with you about some of these. If you do, then you're defeating the purpose of the questions.

  • What do you think you will hate about this job? (This will show if the applicant has done research about the job they are applying for.)
  • Why have you had x amount of jobs in y amount of years? (Questions like these is why you must be able to explain your job gaps and what you did during that time.)
  • What items do people steal from the office to use at home? (If you are an employer and ask this question, why not let employees take such items as long as the amount is reasonable?)
  • Tell me something you have never told anyone else. (Answers could be very interesting, even if they refuse to answer.)
  • Name two things that can cause friction between co-workers. (Dating, parking, tardiness, overtime, etc.)
  • Do you have a secret talent or skill that you don't get to use very much?
  • How would you triple $250 in twenty-four hours?
  • What is your favorite board game and why? (This question could tell you how ambitious a probable employee could be.)
  • How would you go about handcuffing a person with only one arm?
  • How would you go about motivating other co-workers for a project?
  • If I gave you $40,000 to start a business, what kind of business would you start?

I Want More Than 15 Minutes of Fame!

Would you rather be famous or successful?

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Be Careful When Asking Questions - You May Get A Long Answer

Whenever you ask someone "how they've been doing", do you really want them to tell you the truth?

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Heavy Secret

Are you keeping a big secret from someone?

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Would You Rather Questions

These kinds of questions make for great fun at parties. Letting your guests make them up on the fly will give you an insight to what kind of people they are, or you make them up yourself before they arrive.

  • Would you rather have one life lasting 1000 years or live 10 lives at 100 years each?
  • Would you rather have a unicorn as a pet or be a unicorn?
  • Would you rather eat food that you know will make you sick (but not kill you) to keep from offending someone or offend them and lose out on a possible lucrative deal?
  • Would you rather be on the bottom or on the top?
  • Would you rather eat something that is alive or something that has been rotting awhile?
  • Would you rather have fifty $1 dollar bills or one $50 dollar bill?
  • Would you rather have someone be completely honest with you concerning a relationship or lie through their teeth to you about it?
  • Would you rather have smelly feet or bad breath?
  • Would you rather continue living for 100 years or restart your life from the beginning?
  • Would you rather be smacked in the face or smacked on the behind?

Stupid Internet Questions

Are Humans Pack Animals?

Would you rather be alive and alone or about to die with a group of friends?

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Questions and Answers

Would you rather ask a question someone doesn't want to answer or give an answer someone doesn't want to hear?

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Opportunity Makes the Thief

Have you ever stolen anything? (Tell the truth while remaining anonymous; I love the internet.)

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Questions To Spur Interesting Conversation (Hopefully)

  • What is your favorite smell? (fresh cut grass, cow poop, Play-Doh, etc.)
  • Name the top five things to take with you during a zombie outbreak.
  • What has been the weirdest gag gift you have ever given someone?
  • Do you have an opinion on garden gnomes?
  • How would you quickly dispose of a dead body in a hotel room? (I got scared looks when I asked this until I said that I was trying to write a mystery novel. After that, the suggestions came fast and furious.)
  • What board game always ends up having sore losers?
  • Favorite curse word?
  • Name someone you'd like to spend a day with (alive or dead)?
  • Would you tell me a story? (Make sure you have some time, as some of the stories I've gotten have been good, but quite long.)
  • What's your favorite sound? (rainfall, wind through trees, moaning, gunfire, etc.)
  • What super power would you like to have for a day?
  • Have you ever killed anyone? (Most people will walk away; the first time someone looks at you and smiles will send shivers up and down your spine. It's then up to you to go or to listen what that person will say.)

Bad Weather Is So Much Fun!

Would you rather sit in snow while it's falling or dance in the rain?

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What Was That Noise?

Are you afraid of the dark?

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You Are A Tricky One Aren't You?

Asking trick questions to strangers should be carefully considered, as questions like these make people feel kind of "not smart". They hardly ever cause laughter and almost never inspire any type of meaningful conversations. They are more likely to get you a beating or some choice curse words more than anything else. These are best left for friends who don't mind looking stupid in front of you.

What To Do When Death Gives Us The Final Slap

Buried or cremated?

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I Need A Job

What would you do after your boss fires you?

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Questions That You Probably Won't Get An Honest Answer To

Truth is so subjective. People always say they want it, but if someone actually gets it, it almost always causes friction between friends. Is it any wonder why lying is so acceptable?

  • Have you ever spit in someone's food? (If someone said yes, would you ever trust them preparing your food again?)
  • Do I look fat? (Men know this question well, and sometimes even when we tell the truth the person who asks doesn't believe us!)
  • Have you ever bullied anyone? (This question can really put you in a bad light, but can any of us really say that we've never made fun of someone else?)
  • Who did you vote for? (I believe certain people will lie about this question if the result is not what they expected or if they think that telling someone a certain answer will diminish them in the eyes of the person who asked it. As long as you did your research and vote for the person who you think will do the best for the country or office and not for frivolous reasons, you should always be honest.)

Unrequited Love

Are you (at this moment) romantically interested in someone who doesn't think of you in that way?

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Awkward and Uncomfortable Questions For Couples

Robots Could Rule the World

Are you afraid of robots? (Take this question seriously, because it is.)

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© 2017 Don

Feel Free To Tell Others About Your Weird Question Experience

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