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Weird Job Interview Questions That Actually Happened

These are the questions Michael from The Office would’ve asked.

By Micaela Montaña

Published 3 months ago in Funny

Some job interviews throw you curveballs. These? They were pitched straight from another planet. 


In boardrooms and break rooms across America, unsuspecting candidates sat down expecting the usual drill; then got hit with questions so bizarre, you'd swear they were part of a hidden camera show. But no cameras, no scripts; just real people, real interviews, and questions that made time stop.


These moments weren’t just odd, they were unforgettable, awkward, hilarious, and somehow... kind of brilliant. Ready to peek behind the office door and witness the strangest interviews ever conducted? You might laugh. You might cringe. 

  • 1

    Let’s Talk About Your Ex

    "Do you have a girlfriend? Why did you break up with your old girlfriend?"

    Let’s Talk About Your Ex

  • 2

    Alien Believer or Nah?

    "Do you believe in aliens?"

    Alien Believer or Nah?

  • 3

    Guess My Age, Win the Job

    Employer: "How old do you think I am? Guy: "Hmm... I don't know... 40?" Employer: "You have the job. I'm 60."

    Guess My Age, Win the Job

  • 4

    The Tiny Elephant Test

    "If I gave you a tiny elephant right now, what would you do with it?" (I was being interviewed for a job at a nursing home.)

    The Tiny Elephant Test

  • 5

    Accounting... and Baking?

    "I was asked if I knew how to bake. This was for an accounting job."

    Accounting... and Baking?

  • 6

    Shoe or Snack?

    "If you were a shoe, what would you be and why? If you were a food, what would you be and why?"

    Shoe or Snack?

  • 7

    Post-Wipe Inspection

    "Do you look at your s*** after you wipe?"

    Post-Wipe Inspection

  • 8

    GPA Roast Session

    "I was asked a question regarding my GPA during college: 'You finished with a 3.2, but had failed a bunch of classes your first year and a half... What the f*** was up with that?'"

    GPA Roast Session

  • 9

    Free Labor Test

    "Can you stay a few minutes and help me move some furniture?" (It was for an IT job.)

    Free Labor Test

  • 10

    The Great Die Hard Debate

    "I was applying for a Christmas temp job and the last question was, 'Is Die Hard a Christmas movie?'"

    The Great Die Hard Debate

  • 11

    100 Snakes in a Man Suit?

    "Can you provide proof that you are not 100 snakes inside of a hollowed-out man?"

    100 Snakes in a Man Suit?

  • 12

    Wait, WHAT Did You Just Say?

    "So, I see that you're married. Do you f*** around?"

    Wait, WHAT Did You Just Say?

  • 13

    Modeling or Wrestling?

    "You’ve got a broad set of shoulders on you. Have you ever done any modeling or wrestling?"

    Modeling or Wrestling?

  • 14

    Rich People Hot Takes

    "What is your opinion on wealthy people?"

    Rich People Hot Takes

  • 15

    The Tree Within Me

    "If you were a tree, what kind of tree would you be?"

    The Tree Within Me

  • 16

    Filing Mastermind

    "The job entailed a lot of filing of papers, so I got asked, 'How do you best file things in folders alphabetically?' I was like, 'Uh... with a folder for each letter, and then put the folders in alphabetical order...' She said, 'Good... good...' and jotted down some notes."

    Filing Mastermind

  • 17

    Choose Your Pokémon Personality

    "If you could be any of the original 150 Pokémon, which one would you choose?"

    Choose Your Pokémon Personality

  • 18

    Firing Your Future Boss

    "Imagine you had to fire me. How would that go?"

    Firing Your Future Boss

  • 19

    Fruit or Veggie Existentialism

    "Completely technical interview. Then at the end, they asked me, 'If you were a fruit or a vegetable, what would you be and why?'"

    Fruit or Veggie Existentialism

  • 20

    Morals or Money?

    "If this company implemented a policy that you thought was morally wrong, would you still follow said policy?"

    Morals or Money?

  • 21

    What’s Wrong With You?

    "You obviously have a great resume. Why haven’t you gotten another offer yet? Is something wrong with you?"

    What’s Wrong With You?

  • 22

    Job Interviews Make Me Thirsty

    "You want a beer?"

    Job Interviews Make Me Thirsty

  • 23

    Maybe Just A Smooth Criminal, If You Want

    "I had an interviewer continuously ask if I had a criminal record and would not take no for an answer. Surprisingly, I didn’t get that job."

    Maybe Just A Smooth Criminal, If You Want

  • 24

    Classified Military Vibes

    Employer: "Tell me what you did in the military." Guy: "I'd rather not. I kind of need this job."

    Classified Military Vibes

  • 25

    Brick Me Up

    "If you were a brick in a wall, which one would you be?"

    Brick Me Up

  • 26

    Bread Therapy at Panera

    "My friend had an interview at Panera, which ended up being three separate interviews, and she said they made them sit in a circle and talk about the texture of bread and how it made them feel."

    Bread Therapy at Panera

  • 27

    "What’s an Application?"

    "Wasn’t a question, just funny/weird. I was in high school looking for a part-time job, so I went to a local Chinese restaurant and asked for an application. Their response: 'What’s that?'"

    "What’s an Application?"

  • 28

    Stupid People Strategy

    "I was interviewing a potential employee with my supervisor, and the last question he asked her was, 'How are you with dealing with... stupid people?'"

    Stupid People Strategy

  • 29

    Call Your Wife or Your Mom

    "What’s your wife’s number? Say I would call your wife or mother. What would they say is your most annoying habit?"

    Call Your Wife or Your Mom

Categories:

Funny Cringe

Tags:

funny stories funny pictures job work boss
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