240+ Tough Questions to Stump and Confuse Your Friends

Looking for a way to pass the time? These questions will leave you scratching your brain for answers long after you read them! From deep philosophical and existential quandaries to silly shower thought-style brain-breakers and tough trivia q’s, these tough-to-answer questions are sure to give you and your friends something to really think about!

Hard Questions to Answer

Philosophical questions: Why is there war? Is God real? What was your original face before your parents were born?
Relationship questions: Do you believe in true love? Do you feel like we spend enough quality time together?
Icebreakers: What’s the best piece of advice you have ever been given? If you had to teach a class on one subject, what would it be?
Trick questions: Is cereal soup? Why do we say "tuna fish" but not "beef mammal" or "chicken bird"?

Section 1 of 11:

Hardest Philosophical Questions

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There’s no right or wrong answer to these existential questions—which just makes them even more puzzling! Ask these questions at your next hangout to get a serious conversation started—and maybe ignite a few debates:
- Why are there wars?
- What is consciousness?
- Why do we die?
- Why do people fall out of love?
- Where do we go when we die?
- Why do we get old?
- What is the meaning of life?
- Do we have free will, or is everything predetermined?
- Can we ever truly know anything?
- Is there a universal moral truth?
- What happens after death?
- Is our perception of reality accurate?
- What is the ultimate fate of the universe?
- Why do humans experience beauty and art?
- Can good exist without evil?
- What was your original face before your parents were born?
- What is the self?
- Is it possible to have objective meaning in a subjective world?
- Can true altruism exist?
- What is the sound of one hand clapping?
- If everyone in the world suddenly forgot you existed, did you ever truly exist?
- Is there a God?

Section 2 of 11:

Unanswered Scientific Questions

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There’s a lot we know about life, the universe, and everything, but there’s also a great deal we don’t know—sometimes it even seems like the more we discover, the more questions pop up! Can you answer any of these as-yet-unanswered questions about physics, space, and eternity?
- What is the true nature of dark matter?
- What caused the Big Bang?
- What really is gravity?
- Is infinity real, or is it a mental construct?
- How did life evolve from nonliving matter?
- Is there any such thing as the ultimate truth?
- Why does time only go in one direction?
- How was the universe formed?
- What is the universe made of?
- Will the universe end?
- What happens inside a black hole?
- What happens in the gray zone between solid and liquid?
- Do we live in a false vacuum?
- Where does a flame go when it goes out?
- Is there order in chaos?
- Why is there more matter than antimatter?
- Is string theory correct?
- If humans could see more of the electromagnetic spectrum, what would colors look like?
- What is the purpose of the universe?
- Are numbers and mathematical concepts real or invented?
- What is the nature of time—does it exist independently of perception?
- How does the universe work?
- Is there a multiverse, and if so, how could we prove it?
- What lies beyond the observable universe?
- Why does the universe exist at all?

Section 3 of 11:

Hardest Moral & Ethical Questions

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These ethical dilemmas and questions about morality will either stump your friends, or they’ll tell you a lot about your friends’ values and moral code. There’s no “correct” answer, but the respondents’ logic behind their choice is sure to give you insight into their character:
- The trolley problem: A trolley has lost its brakes and is hurtling down the track. If the trolley continues on its track, it will hit 5 workmen. You have the ability to pull a lever and switch the trolley to another track, where it will hit 1 workman, who would die when the trolley hits him. Do you pull the lever and sacrifice 1 person, or do nothing and let the trolley hit 5 people?
- Say you make a purchase at a store, and the cashier gives you too much change. Do you say something or keep quiet?
- Is there such a thing as right and wrong? How do you decide what’s right and wrong?
- What is the most important principle you live your life by?
- Your friend gives you a perfume or cologne for your birthday, not realizing you’re allergic. Do you tell her and ask for a receipt so you can return it? Or do you keep quiet?
- You receive a package meant for your neighbor. The package is from your favorite store. You know the original addressee will likely get a free replacement by the company. Do you keep the package or deliver it to their house?
- Do you think animals and humans are equal? Why or why not?
- Is killing someone always wrong? When, if ever, is it OK?
- Would you let an innocent person die to save 20 other people?
- There is a button that, when pushed, grants you a million dollars instantly—but it also kills someone in the world at random. Do you push the button?

Section 4 of 11:

Hardest Relationship Questions

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These questions about love and relationships might have answers, but that doesn’t mean they’re easy to answer. These deep and probing questions will give you insight into your partner’s values, history, dreams, fears, and more, as well as help you understand more about your relationship, your compatibility, and your future together.
- Do you feel like we spend enough quality time together?
- How do you feel about our sex life?
- Are you happy with the way we share responsibilities?
- Is there anything you have been hesitant to talk to me about?
- Do you believe in true love?
- How do you feel about our financial situation and how we handle money?
- What is something I do that hurts you?
- What relationship models did you have in your childhood?
- What passion or project reflects your true authentic self?
- What does long-term happiness look like to you?
- How do you see your purpose evolving?
- Have you ever idolized a relationship?^{[1]
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- What question do you wish people asked you more often?
- Do you ever want to get married?
- What part of your personality do you feel is misunderstood?
- What’s something you once believed about being romantic that you no longer do?
- What advice would you give your future self about relationships?
- How have your family dynamics affected your outlook on relationships?
- What does cheating mean to you?
- Have you ever felt tempted to cheat on me?
- Do you feel like I support you in your personal goals and ambitions?
- Where do you see our relationship in the next 5 years?
- Do you feel emotionally fulfilled in the relationship?

Section 5 of 11:

Hard Questions to Ask Yourself

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Where do you see yourself in 5 years? In 10 years? What is your life purpose? Asking yourself tough questions about your identity and goals can be…well, tough! But it’s important to spend regular time checking in with yourself and reflecting on your progress and goals in life to make sure you’re living the life you’ve always wanted. Try asking yourself some of these difficult questions:
- Where do I see myself in 5 years?
- Where do I see myself in 10 years?
- What matters most to me in life?
- What is my life’s purpose?
- How important is my own happiness?
- Who has had the greatest impact on my life?
- Am I taking anything for granted?
- Am I putting enough effort into my relationships?
- What is my greatest challenge?
- What type of friend do I want to be?
- What’s my biggest weakness?
- What’s my biggest strength?
- What is one way I can better my life in the next year? month? week? today?
- When do I feel my best?
- When do I feel at my worst?
- How comfortable am I with saying “no” to things?
- Am I a good example for those around me?
- What relaxes me when I’m feeling stressed?
- Do I embrace or avoid how I’m feeling?
- Am I generally in control of my emotions?
- What motivates me every day?
- What makes me feel proud of my work?
- What is standing in between me and my own happiness?
- What are the main components that make up a good life?
- What would I do with my life if there were no limitations?
- What lesson did I learn the hard way?
- What’s the best part about being me?
- What are my top 5 personal values?
- Do I enjoy my own company? If not, how can I start to?
- What is the difference between settling and accepting?^{[2]
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Section 6 of 11:

Random Hard Icebreaker Questions

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Getting to know someone has never been more fun—or more…weird. We’re positive your friends and loved ones haven’t given most of these silly get-to-know-you questions a thought before—and we’re also positive they’ll have strong feelings about some of them!
- Cats or dogs?
- What’s the best piece of advice you have ever been given?
- If you had to teach a class on one thing, what would you teach?^{[3]
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- Which do you pour first when making cereal, the milk or the cereal?
- If you could hang out with any cartoon character, who would you choose and why?
- If you could add a word to the dictionary what would you add and what would it mean?
- Would you rather be about to teleport or be able to read minds?
- If you could meet any living person for dinner, who would you pick and why?
- What is your most used emoji?
- Would you rather have invisibility or flight?
- Crunchy peanut butter or smooth?
- Sweet, salty, or sour?
- If you could be an animal, what animal would you be and why?
- If you could bring back any fashion trend, what would it be?
- If you had to eat one meal every day for the rest of your life what would it be?
- If you had 25 hours a day, how would you spend your extra time?
- If you had to delete all but three apps from your smartphone, which ones would you keep?
- Coffee or tea?
- Which superpower would you rather have: invisibility or flight?

Section 7 of 11:

Hardest Funny Questions

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Is cereal soup? How many holes does a straw have? If you’re waiting for the waiter, aren’t you the waiter? These silly questions may not have any answers, but they’re sure to elicit a few groans!
- Is cereal soup?
- If you bake 2 lasagnas and then stack one on top of the other, how many lasagnas do you have?
- Why doesn't Tarzan have a beard?
- Why do cats always land on their feet but toast always lands butter side down?
- Why do we say "tuna fish" but not "beef mammal" or "chicken bird"?
- If you’re waiting for the waiter, aren’t you the waiter?
- Is a hot dog a sandwich?
- How many holes does a straw have?
- Why do we say "working like a dog" when dogs just lie around all day?
- Is "go to bed; you'll feel better in the morning" just the human version of "Did you turn it off and turn it back on again?"
- Why do we say something is “on fire” when really the fire is on the thing?
- If James Bond is the most famous spy, wouldn't that also make him the worst spy?
- Do crabs think that fish can fly?
- Do crabs think that humans walk sideways?
- Why are they called fire trucks when they carry water? Shouldn’t they be called water trucks?
- Which orange came first—the color or the fruit?
- To my stomach, aren’t all potatoes mashed?
- When my dog brings me a toy, is it because it’s her favorite toy or because she thinks it’s my favorite toy?
- Why did Sally sell seashells by the seashore when you can just pick them up off the ground for free?
- Are those who sneeze a lot the most blessed?
- If you have a PhD, is every meeting you go to a doctor’s appointment?
- If the #2 pencil is the most popular, why is it still #2?
- If two mind readers read each other's minds at the exact same time, whose thoughts are they reading?
- Why don't you meet more people named Elvis if Elvis Presley was so popular?
- How do nudists clean their glasses?
- How come a group of squids isn’t called a squad?
- Do sheep get static cling when they rub against one another?
- When you clean a vacuum cleaner, do you become the vacuum cleaner?
- Is peanut butter a liquid or a solid?

Section 8 of 11:

Hardest Trick Questions

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Is water wet? When does "now" end and "then" begin? Why is the expression “caught between a rock and a hard place” when a rock is a hard place too? These impossible shower thought-esque questions will make you laugh or break your brain—or both! Ask your friends some of these unanswerable questions to get the giggles going:
- If you're caught "between a rock and a hard place," isn't the rock a hard place too?
- When does "now" end and "then" begin?
- Why do we wash bath towels? Aren't we clean when we use them?
- Is water wet?
- Can you daydream at night?
- If we could hear our pets' thoughts, would we be amazed or disappointed?
- Why do we say ‘sleeping like a baby’ when babies often wake up crying and restless?
- What if déjà vu is just you losing a life and starting again at the last checkpoint?
- How many times have I almost died without even realizing it?
- If money is the root of all evil, how come churches always ask for it?
- What did my dog name me?
- Why do we call it a building if it's already built?
- Isn’t your first birthday technically your second birthday?
- Why do "fat chance" and "slim chance" mean the same thing?
- Why is a raven like a writing desk?
- Where does your lap go when you stand up?
- Why is a boxing ring square?
- Why do we say an alarm is “going off” when it's actually turning on?
- What color is a mirror?

Section 9 of 11:

Hardest Riddles

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These questions do have answers—but you probably won’t guess most of them! Some of the riddles in this section are complicated logic puzzles, but others are…well, so dumb, they’re actually brilliant. See if your friends can figure out the answers to some of these brain-teasers:
- Q: What has five fingers but isn’t a hand? A: A glove.
- Q: Which word in the dictionary is always spelled incorrectly? A: “Incorrectly.”
- Q: He has married many men but has never been married. Who is he? A: The minister.
- Q: I have a head like a cat and feet like a cat, but I am not a cat. What am I? A: A kitten.
- Q: What is always coming but never arrives? A: Tomorrow.
- Q: What is it that lives if it is fed, and dies if you give it a drink? A: Fire.
- Q: What can be broken but never held? A: A promise.
- Q: What never asks a question but gets answered all the time? A: A phone.
- Q: What are two things you can never eat for breakfast? A: Lunch and dinner.
- Q: What word would you use to describe a man who does not have all his fingers on one hand? A: Normal.
- Q: What goes up but never comes down? A: Your age (or the rent).
- Q: A girl fell off a 50-foot ladder but didn’t get hurt. How come? A: She fell from the bottom step.
- Q: What is caught but never thrown? A: A cold.
- Q: What starts with “e” and ends with “e” but only has one letter in it? A: An envelope.
- Q: If a plane crashes on the border between the United States and Canada, where do they bury the survivors? A: Nowhere—they survived!
- Q: If you have one, you want to share it. But once you share it, you do not have it. What is it? A: A secret.
- Q: How can a person go 25 days without sleep? A: They sleep at night.
- Q: You spot a boat full of people but there isn’t a single person on board. How is that possible? A: Everyone on board is married.
- Q: If it takes eight men ten hours to build a wall, how long would it take four men? A: No time at all—the wall is already built.
- Q: If you have a bowl with six apples and you take away four, how many do you have? A: Four.
- Q: How do you make the number one disappear? A: Add a “G” to the front and it’s “gone.”

Section 10 of 11:

Hardest Answerable Science Questions

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Not all hard questions are impossible to answer! These scientific queries are technically answerable…but they’ll take a bit of time and mental energy to figure out. Check out these questions when you’re in the mood for a real challenge:
- Q: How long is the lifespan of a human red blood cell? A: 120 days.
- Q: Where on the human body is the pinna? A: The ear.
- Q: Of the three smallest bones in the human body, which one is also referred to as the Hammer? A: The malleus.
- Q: Entomology is the study of what? A: Insects.
- Q: Which type of living organism produces most of the Earth's oxygen? A: Phytoplankton.
- Q: What is the longest type of cell in the body? A: Nerve Cell (or Neuron).
- Q: Which animal possesses the largest brain relative to its body size? A: The sperm whale.
- Q: What is the only species of bear found in the Southern Hemisphere? A: Spectacled bear.
- Q: In what year was the structure of DNA discovered? A: 1953.
- Q: How many bones are there in a human foot? A: 26.
- Q: The word "muscle" comes from a Latin word meaning what? A: Little mouse.
- Q: What is the only metal that is liquid at room temperature? A: Mercury.
- Q: What does a Geiger counter measure? A: Radiation.
- Q: What is the hottest planet in our solar system? A: Venus.
- Q: What was the first vegetable to be grown in space? A: A potato.
- Q: How many bones do sharks have? A: None.
- Q: What animal has 3 hearts? A: An octopus.

Section 11 of 11:

Hardest Trivia Questions

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Do you know what the highest-grossing Broadway show is? Or what the first 22 cards in a tarot deck are called? How about the human body’s largest organ? Brush up on your science and historical facts, pop culture knowledge, and other random trivia q’s and crush the competition at the next trivia night!
- Q: What is the body’s largest organ? A: The skin.
- Q: What is Lana Del Rey’s real name? A: Elizabeth Woolridge Grant.
- Q: What is the longest-running Broadway show? A: The Phantom of the Opera.^{[4]
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- Q: What about the highest-grossing Broadway show? A: The Lion King.
- Q: What is Carrie’s last name in Sex and the City? A: Bradshaw.
- Q: What is the longest above-water mountain range? A: The Andes.
- Q: What year did Netflix introduce streaming services? A: 2007.
- Q: What is the deadliest animal in the world, besides humans? A: Mosquitos.
- Q: What is the capital of Singapore? A: Singapore.
- Q: What are the first 22 cards in a tarot deck called? A: The Major Arcana.
- Q: What was the first country to give women the right to vote? A: New Zealand.
- Q: Who in Greek mythology was known as the messenger of the gods? A: Hermes.
- Q: To which artist is this quote attributed? “I am my own muse. I am the subject I know best. The subject I want to know better.” A: Frida Kahlo.
- Q: What are the names of the four March sisters in Little Women? A: Meg, Jo, Beth, and Amy.
- Q: What is the largest desert in the world? A: Antarctica.
- Q: Aureolin is a shade of what color? A: Yellow.
- Q: What is the smallest country in the world by land area? A: Vatican City.
- Q: What is the 4th letter of the Greek alphabet? A: Delta.
- Q: What celebrity was the world’s first cloned animal, a sheep, named after in 1996? A: Dolly Parton.
- Q: How many bones are there in the human body? A: 206.
- Q: Who was the first Black justice on the Supreme Court of the U.S.? A: Thurgood Marshall.
- Q: What is the main character’s name in The Handmaid’s Tale? A: Offred.
- Q: In what city were the first infections of COVID-19 discovered? A: Wuhan, China.
- Q: In chess, what direction can a bishop move? A: Diagonally.
- Q: What’s the shortcut for the paste function on most computers? A: Ctrl+V.