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Weird Questions to Ask People


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.

Asking funny, odd or weird questions should be something everyone does once in a while. If you're lucky enough, the person you decide to present your question to will not only answer it, but a great discussion will be the result of it. The bottom line is that the interaction will be memorable.

I've never understood the boring conversation starters that 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. This is where a good question can come in handy. 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 that you can actually answer because the internet and anonymity go hand in hand (a rare opportunity for sure); take advantage of it.

Weird Questions to Ask People

These questions are sure to provoke a response from just about anyone. You can also answer some of these questions in the polls throughout this article!

  • Have you ever lied to a priest, preacher or holy man?
  • Have you ever borrowed something and just haven't never returned it yet? (Is it considered stealing if you plan on returning it?)
  • Have you ever opened and re-wrapped a present that had your name on it? What about someone else's name?
  • Would you rather be a hero or a villain for a day? (And what would you do?)
  • Would you rather be alive and alone or about to die with a group of friends?
  • Whenever you ask someone "how they've been doing," do you really want them to tell you the truth?
  • Have you ever dropped food on the floor and then picked it up and eat it?
  • Have you ever had to run from the police?
  • Would you rather know when you're going to die or how you're going to die?
  • Are you keeping a really big secret from someone?
  • Have you ever been outsmarted by another person?
  • Would you ever take a lie detector test with a loved one asking the questions?
  • Would you rather ask a question someone doesn't want to answer or give an answer someone doesn't want to hear?
  • Would you rather sit in snow while it's falling or dance in the rain?
  • Do you like kids and everything that comes with them?
  • Do you want to be buried or cremated?
  • Are you afraid of the dark?
  • Are you (at this moment) romantically interested in someone who doesn't think of you in that way?
  • Have you ever been arrested?
  • How many people have you slept with? This is a confrontational question when asked by someone you're in a relationship with, so be prepared.
  • What would you do after your boss fires you?
  • Have you ever purposely hurt someone just enough to make them scream when rendering first aid?
  • Are you afraid of robots?

A Question Mark Is The Same As a Double-Edged Sword

You're going to find a lot of interesting questions below, covering all sorts of weird topics. Feel free to answer those you feel comfortable with, but I'll leave it up to you to decide if you want to ask some of the questions to people in real life. If you do decide to ask such questions in real life, just be prepared for some answers you may or may not want to hear.

  • Weird questions to ask people.
  • "Would you rather" questions.
  • Questions to spur interesting (and sometimes uncomfortable) conversations.
  • Questions you probably won't get an honest answer to.
  • Strange and interesting interview questions for jobs.
  • Questions that will make people mad, happy or uncomfortable.

How About A Few Embarrassing Questions?

"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 into what kind of people they are, or you make them up yourself before they arrive and pick out questions at random.

  • 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? (Depends on the situation!)
  • Would you rather eat something that is alive or something that has been rotting awhile?
  • Would you rather have no heating / air conditioning or no internet?
  • 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 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?

A prudent question is one-half of wisdom.

— Francis Bacon

Fun Questions Usually Result in an Interesting Conversation

  • 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?
  • If all of a sudden we could understand animals, which one do you think would sound more intellectual? The nicest? The most unlikable?
  • Do you have an opinion on garden gnomes or pink flamingos?
  • What's your favorite weird or unusual smell? (Mine is cow poop. Not up close, of course.)
  • How would you dispose of a dead body if you only had an hour to get rid of it?
  • 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 and an example on how you use it?
  • 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 superpower 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.)

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 not to 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 researched 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.)
  • Tell me how you would restrain 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?

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... even if it were a friend you asked?)
  • Do I look fat? (Men know this question well, and even when we tell the truth the person who asks doesn't believe us!)
  • Have you ever bullied anyone? (This question can 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

Weird Interview Questions (And How To Answer Them)

Retired Questions That I May Bring Back At Some Point

  • Ever had an imaginary friend? (41% yes; 59% no)
  • Famous or successful? (14% want fame; 86% want success)
  • Have you ever killed anyone? (19% said yes; 81% said no)
  • Still a virgin? (52% said yes; 21% said no; 27% uncertain)

© 2017 Don

Feel Free To Tell Others About Your Weird Question Experience

Maurice Glaude from Mobile on July 06, 2019:

I didn't answer all the polls or read the entire article but maybe one day I might.

Beth Webster-Duerr from Henrietta, New York on March 02, 2019:

Fun question and answer polls. Answered 'em all, even without fudging. A few forced an answer that may not apply like the burial and virgin questions, but then maybe you intended an either/or scenario.

The newest questions i have seen on Facebook:

Would you trade your internet to live in a mansion/secluded cottage,: Would you give up the internet for 1 week for 1 million dollars?

Well, something like that. I won't answer like farm questions on Facebook, but if you add them here, do let me know.

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