Unlocking Laughter: 100 Best Would You Rather Questions For The Office Fan

The sitcom *The Office* remains a beloved series, and its enduring popularity has given rise to various forms of fan engagement. Among these, “Best Would You Rather Questions For The Office” stand out as a fun and engaging way to explore the show’s characters, scenarios, and humor. This article provides a comprehensive collection of 100 of these questions, designed to spark lively conversations and entertain any *Office* enthusiast.

What Makes These Questions So Great?

“Best Would You Rather Questions For The Office” tap into our fondness for the show by presenting us with dilemmas rooted in its quirky world. They force us to consider how our favorite characters might react in absurd situations, or how we ourselves would navigate the perils and perks of Dunder Mifflin. The popularity of these questions lies in their ability to blend humor, nostalgia, and personal opinion, creating a shared experience for fans.

These aren’t just any random “Would you rather” questions; they’re specifically tailored to the nuances of *The Office*. This means they often involve inside jokes, character traits, and memorable episodes. They’re frequently used in a few ways:

  • Icebreakers at *Office*-themed parties
  • Conversation starters among friends who love the show
  • Creative writing prompts for fan fiction

Furthermore, these questions provide an opportunity to analyze the characters’ motivations and values. For example, consider the following simple comparison. It helps you evaluate your priorities.

Option A Option B
Work for Michael Scott forever Work for Jan Levinson for one year

Ethics and Morality at Dunder Mifflin: Would You Rather?

  1. Would you rather cover up for Dwight’s fire safety negligence or tell Michael and risk being the office pariah?
  2. Would you rather sell out a coworker to save your own job or stand by them and risk unemployment?
  3. Would you rather lie to a client to close a sale or lose the sale and be honest?
  4. Would you rather pretend to like Michael’s improv show or tell him it’s terrible?
  5. Would you rather get fired for sleeping with your boss or get passed over for a promotion because you didn’t?
  6. Would you rather accidentally reveal someone’s secret or keep it to yourself even if it hurts them?
  7. Would you rather take credit for someone else’s idea or let someone else take credit for yours?
  8. Would you rather let Michael believe a lie he made up or correct him and ruin his fun?
  9. Would you rather let Dwight get away with something unethical or report him and face his wrath?
  10. Would you rather let Angela’s cats suffer or take care of them yourself?
  11. Would you rather let Andy embarrass himself on stage or tell him he’s terrible at singing?
  12. Would you rather tell Pam that Jim is cheating on her with Cathy or keep it a secret?
  13. Would you rather tell Oscar and Kevin that Michael is making fun of them or stay silent to keep the peace?
  14. Would you rather tell Phyllis the truth about Bob Vance or let her continue to be naive?
  15. Would you rather be responsible for the downsizing or lose your job and blame someone else?
  16. Would you rather stay quiet when you witness Michael committing a serious offense or confront him directly?
  17. Would you rather witness Jim pranking Dwight or stop him from taking it too far?
  18. Would you rather be the one to tell Michael that Dunder Mifflin is closing or leave it to someone else?
  19. Would you rather fire someone or be fired?
  20. Would you rather get a promotion you didn’t deserve or be overlooked for one you did deserve?
  21. Would you rather save the company money by using cheaper supplies or maintain the quality and risk budget cuts?
  22. Would you rather be in charge of the party planning committee or completely avoid office parties?
  23. Would you rather report your boss for sexual harassment or quit and find another job?
  24. Would you rather participate in a racist joke to fit in or speak out against it and risk being ostracized?
  25. Would you rather lie to HR to protect a coworker or tell the truth and potentially get them fired?
  26. Would you rather keep quiet about an affair in the office or tell the affected spouse?
  27. Would you rather accept a bribe to look the other way or do the right thing and risk your career?
  28. Would you rather let Michael win an argument even if he’s wrong or prove him wrong and humiliate him?
  29. Would you rather let Andy take all the credit for your work or speak up and risk his anger?
  30. Would you rather let Dwight continue his bizarre “Dwight Schrute, Manager” antics or report him to corporate?
  31. Would you rather let Angela mistreat the other employees or confront her about her behavior?
  32. Would you rather be forced to participate in one of Michael’s horrible skits or refuse and be the laughing stock?
  33. Would you rather be Michael’s favorite employee or be ignored by him completely?
  34. Would you rather be Dwight’s number 2 or Jim’s best friend?

Relationships and Romance in Scranton: Would You Rather?

  • Would you rather date Michael or Dwight?
  • Would you rather be married to Angela or Meredith?
  • Would you rather be in a love triangle with Jim and Pam or Ryan and Kelly?
  • Would you rather go on a double date with Michael and Jan or Dwight and Angela?
  • Would you rather give relationship advice to Michael or Dwight?
  • Would you rather be set up on a blind date with Kevin or Stanley?
  • Would you rather have Phyllis as your mother-in-law or Meredith as your sister-in-law?
  • Would you rather attend a wedding hosted by Michael or Dwight?
  • Would you rather be Jim or Pam in their relationship?
  • Would you rather have Ryan as your assistant or your boyfriend?
  • Would you rather be stuck on a deserted island with Angela or Kelly?
  • Would you rather be in a relationship where the only form of communication is through post-it notes, à la Jim and Pam or through Dwight’s various forms of survival techniques?
  • Would you rather be in a relationship where the proposal is interrupted by a bear or one where you have to wait for the person to propose?
  • Would you rather have your wedding at Niagara Falls or in a beet field?
  • Would you rather be married by Michael or a random Justice of the Peace?
  • Would you rather find out your partner cheated on you during a company picnic or at a Halloween party?
  • Would you rather have your first dance be to “Forever” or “The Little Drummer Boy”?
  • Would you rather be serenaded by Andy or Michael?
  • Would you rather be courted by Michael’s alter ego, Date Mike or Date Dwight?
  • Would you rather find out your partner is in love with your best friend or with your sibling?
  • Would you rather have your partner try to win you back with a grand gesture or through simple acts of kindness?
  • Would you rather have Michael and Jan as your marriage counselors or Dwight and Angela?
  • Would you rather be in a relationship where the guy is always pulling pranks on you or one where he’s always trying to control you?
  • Would you rather have your partner get drunk at a company Christmas party or fall asleep during a romantic dinner?
  • Would you rather have a partner who’s obsessed with beets or one who’s obsessed with ninjas?
  • Would you rather have your partner embarrass you in front of your friends or in front of your boss?
  • Would you rather be serenaded by Michael Scott with a personalized song or receive a romantic poem written by Dwight Schrute?
  • Would you rather be in a relationship where you can never tell when your partner is joking or one where they’re always too serious?
  • Would you rather have a partner who constantly compares you to their ex or one who pretends their ex never existed?
  • Would you rather get a love letter from Dwight Schrute or a romantic email from Michael Scott?
  • Would you rather go on a date with Michael and have him spend the entire time talking about himself or go on a date with Dwight and have him spend the entire time talking about bears, beets, and Battlestar Galactica?
  • Would you rather have a partner who constantly tries to impress you or one who doesn’t try at all?
  • Would you rather have a partner who’s completely clueless about social cues or one who’s overly sensitive to them?
  • Would you rather find your soulmate at Dunder Mifflin or never work there at all?

Careers and Office Life: Would You Rather?

  1. Would you rather be Michael’s assistant or Dwight’s number two?
  2. Would you rather work in the annex with Toby or in the warehouse?
  3. Would you rather be in charge of party planning or safety training?
  4. Would you rather have to work overtime every day or deal with Michael’s antics?
  5. Would you rather sell paper with Dwight or make sales calls with Michael?
  6. Would you rather be stuck in a meeting with Jan or a seminar with Ryan?
  7. Would you rather have to work under David Wallace or Robert California?
  8. Would you rather give a presentation with Michael or give a presentation to Michael?
  9. Would you rather have to cover for Michael’s mistakes or Dwight’s accidents?
  10. Would you rather be the one to fire someone or be the one who gets fired?
  11. Would you rather work in the Scranton branch forever or be transferred to the Stamford branch?
  12. Would you rather have to participate in Michael’s improv classes or Dwight’s survival exercises?
  13. Would you rather be stuck in an elevator with Michael or in a car with Dwight?
  14. Would you rather have to listen to Michael’s motivational speeches or Dwight’s safety lectures?
  15. Would you rather be the target of Jim’s pranks or Dwight’s revenge?
  16. Would you rather be the one who has to clean up after a party or the one who has to organize it?
  17. Would you rather work with a boss who takes all the credit or one who blames you for everything?
  18. Would you rather have a job you love but pays little or a job you hate but pays a lot?
  19. Would you rather be forced to work with Toby Flenderson on a daily basis or have to listen to Michael Scott’s terrible jokes on repeat?
  20. Would you rather have to participate in Michael’s cringeworthy diversity training or Dwight’s ridiculous volunteer sheriff program?
  21. Would you rather have your work evaluated by Jan Levinson or by Dwight Schrute?
  22. Would you rather be stuck on a sales call with Michael or on a customer service call with Dwight?
  23. Would you rather have a job where you never get recognized for your hard work or one where you’re constantly under scrutiny?
  24. Would you rather be the office gossip or the office outcast?
  25. Would you rather have to work with a coworker who steals your ideas or one who constantly undermines you?
  26. Would you rather have a job that’s boring but stable or one that’s exciting but unpredictable?
  27. Would you rather be stuck in a sales meeting with Michael, where he refuses to follow the agenda, or in a strategic planning session with Dwight, where he insists on incorporating survivalist tactics?
  28. Would you rather be forced to participate in one of Michael’s terrible business schemes or Dwight’s bizarre productivity experiments?
  29. Would you rather have your career path dictated by Jan Levinson or by Ryan Howard?
  30. Would you rather be stuck managing the office finances under Michael’s direction or be in charge of IT security according to Dwight’s rules?
  31. Would you rather be the subject of one of Jim’s elaborate pranks or the victim of one of Dwight’s security protocols?
  32. Would you rather have your job performance reviewed by Michael or Dwight?
  33. Would you rather be Michael’s right-hand man or Dwight’s personal assistant?
  34. Would you rather work for a company that is constantly downsizing or one that is always micromanaging?

In conclusion, “Best Would You Rather Questions For The Office” are more than just a fun game. They’re a gateway into the heart of the show, allowing fans to relive its most memorable moments and explore the personalities of its beloved characters. By posing difficult and humorous choices, these questions spark engaging discussions and provide a unique way to connect with fellow *Office* enthusiasts.