Whether you are just getting to know someone or are looking to find a way to spice up a conversation with a partner or friend, engaging in insightful trivia questions can keep the entertainment going. Here, we discuss 60 of the hardest 'would you rather' questions to keep conversations exciting.

Some of the good 'would you rather' questions can help add some exciting conversation into an otherwise mundane day and is also an excellent way to learn more about someone's likes, dislikes and thinking patterns. Here, we give you some great ways to get to know each other better while having fun with 'would you rather' questions for adults to funny questions to keep things interesting.

What are the most difficult questions?

The most challenging things to ask someone include making them choose between equally unpleasant scenarios or between two things they are equally fond of. The hardest 'would you rather' questions for adults are just some of the ways you can invoke these thought-provoking conversations.

By making them choose between these options, you can pick their brain and see what gets them ticking and what they value most in a light-hearted way. Here are different topics to pick and choose from.

Funny 'would you rather' questions

  • Would you rather have to write everything you say out by hand or only be able to speak in rhymes?
  • Have no eyelashes or no eyebrows?
  • Have to skip everywhere instead of walking or singing instead of being able to speak? 
  • Switch bodies with a sibling or switch bodies with a grandparent?
  • Have to climb in through the window or shower with your clothes on? 
  • Have bananas for fingers or bananas for toes?
  • Have your only mode of transportation be a donkey or a giraffe?
  • Be famous, have no privacy, be a hermit, and have no one care about you?
  • Have to shout 'HOORAY' every time you hear your name or do five jumping jacks whenever you see a baby?
  • Have to eat only broccoli for the rest of your life or be forced to watch an episode of Keeping Up with the Kardashians every day?
  • Only be able to speak in rhyme or only be able to speak in alliteration?
  • Have to make a one-minute speech in front of 10,000 people or kiss a frog?
  • Have a face that everyone laughs at or a name that everyone laughs at?
  • Be trapped in a romantic comedy with your enemies or trapped in a horror movie with your friends?
  • Have every movie a musical or every store had a soundtrack? 
  • If you had to choose, would you rather every shirt you put on be slightly itchy or only be able to use single-ply toilet paper?
  • Be someone’s pet goldfish or a wild lizard?
  • Have an elephant’s trunk attached to your face or a neck as long as a giraffe's? 
  • Grow a ponytail down to your ankles, or have a giant Adam's apple?
  • Have no one laugh at any of your jokes or not be able to laugh at anyone else’s jokes?

Hardest 'would you rather' questions from Reddit

  • Have the ability to fly only while holding a real duck or have the ability of telekinesis but only when soaked waist-down in milk?
  • Every song you listen to slowly turns into All-Star by SmashMouth, or every movie you watch slowly turns into Shrek?
  • Lay in a bed full of dead crickets or a bed full of live crickets?
  • Burn to death once or drown twice?
  • Stay in school for the rest of your life or get a job in the real world immediately when you turn four?
  • Be fluent in all languages or able to play all musical instruments beautifully?
  • Sing like Freddie Mercury or dance like Michael Jackson?
  • Outlive your entire family, or be the first among them to die?
  • Know exactly when you die but not how, or know precisely how you will die but not when?
  • Lose your sense of taste or both feet?

Crazy 'would you rather' questions

  • Eat the oldest thing in your fridge or drink from your toilet?
  • Swim in a pool full of Nutella or a pool full of maple syrup?
  • Puke on your hero, or have your hero puke on you?
  • Be reincarnated as a hippo or a snail?
  • Lose your sight or your memories?
  • Find a rat in your kitchen or a cockroach in your bed?
  • Die in 20 years with no regrets, or live to 100 with many regrets?
  • Have to wear every shirt inside out or every pair of pants backwards?
  • Buy all used underwear or all used toothbrushes?
  • Have seven fingers on each hand or seven toes on each foot?

Hardest 'would you rather' questions for couples

  • Travel with your significant other or best friends?
  • Go back to the past and meet your loved ones who passed away or go to the future to meet your children or grandchildren-to-be?
  • Forget your partner's birthday or your anniversary every year?
  • Have a relationship like Jim and Pam from The Office or Nick and Jess from New Girl
  • Invite someone you just met to be your +1 to a wedding, or go solo?
  • Have another ten years with your partner or a one-night stand with your celebrity crush?
  • Have a personal maid or a personal chef?
  • Work an overtime shift with your annoying boss or spend an entire day with your mother-in-law?
  • Ask your ex-partner or a stranger for a favour?
  • People know all the details of your finances or all the details about your love life?

'Would you rather' questions for couples 18+

  • Walk in on your parents or have them walk in on you?
  • Lick ice cream off someone’s body or whipped cream?
  • Receive lingerie or dirty toys as a gift?
  • Kiss a coworker or friend?
  • Go to bed alone forever or share a bed with someone forever?
  • Bite someone’s ear or bite someone’s lip?
  • Give one presentation naked, or never see your partner naked again?
  • Kiss someone with cherry-flavoured lip balm or cake batter-flavoured lip balm?
  • Meet someone on a dating app or at a bar?
  • Kiss a random person or kiss your roommate?

Any of these hardest 'would you rather' questions are sure to keep friends and couples entertained. Keep each other on your toes and learn more about each other through these thought-provoking questions.

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