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350 Weird Questions to Ask – A Master List

350 Weird Questions to Ask – A Master List

Updated on Nov 07, 2023

Reviewed by Katina Tarver, MA (Mental Health and Wellness Counseling) , Life & Relationship Coach

350 Weird Questions to Ask - A Master List

Sometimes conversations can really get toned down because there is not enough good, bad, silly, or crazy stuff to ask someone. You may have faced such a situation many times. Right?

Whether you are sitting in a group chat with friends or family, or in an informal small talk with colleagues in an office canteen, weird questions to ask someone can make all the difference in a tiresome conversation.

These questions may apparently look bizarre and odd but they can brighten up any mutual discussion very easily and can motivate people to continue, rather than to turn down and walk away from the chat session.

In this article. We will incorporate 350 weird questions in one place that can be asked in various situations to build up closer connections and rejuvenate boring and tedious conversations successfully.

350 Weird Questions to Ask - A Master List
350 Weird Questions to Ask – A Master List

What are weird questions to ask someone?

There is no doubt about the fact that amazing conversations can only happen if you have the correct blend of deep questions, fun queries, or quirky and eerie inquiries that are mind-boggling and can create an aura of interest in any discussion.

Weird questions are strange, offbeat, and hilarious and you should keep a few of them ready with you whenever you meet old pals, or sit somewhere casually with office colleagues.

These questions have the power to make the other person think and wonder about how to answer them in the right way, without falling into a trap of laughter and amusement by others.

Sometimes, this random nonsense stuff can help us get to know each other well.

So let’s get started…

Weird questions to ask a guy

Whenever you are planning to ask weird questions to a guy, make sure to use strange queries based on random thoughts and odd mind musings that apparently appear meaningless and bizarre.

In no time, you will find him struggling to answer and he may find himself already fallen in an awkward position. Do you really want to try it out?

So, let’s begin

  1. How many times do you lie in a day? Have you ever counted?
  2. Did you ever try to eat an ant? Why or why not?
  3. How can you swim in a bathtub? Explain with a live demo.
  4. Tell me something about your big doubts.
  5. What soap do you use to wash your hands? Do you carry it with you wherever you go?
  6. Why is it commonly called ‘ice tea’ and ‘cold coffee’? Why can’t it be known the other way round? Do you have any ideas?
  7. Is there any song that annoys you easily? Why?
  8. Name a childhood silly thing that you would still love doing.
  9. How many times do you change your clothes in a day?
  10. What does your wardrobe look like? Is it neat or messy?
  11. Have you ever thought of touching a snake?
  12. Who do you miss the most in your life? Why?
  13. How many times does your mom yell at you in a day?
  14. What’s the worst thing about being a man?
  15. What are your views about male baldness? Why do most women not like bald men?
  16. How are dogs different from cats as a pet?
  17. What would happen if every human on this planet lived for 100 years? Will the Earth look overcrowded?
  18. Which music video can you watch over and over again without getting bored?
  19. How well do you handle pressure situations?
  20. With whom will you never win a verbal fight? Why?
  21. What crazy things do you do very often?
  22. Do you think humans are less disciplined than animals? Why?
  23. Have you ever slept with your pet? How does it feel? Do they snore?
  24. What is the worst, yet famous historical place you have visited? Why do you think it is worse?
  25. Describe your morning ritual without which you never start your day.
  26. How many times in a week do you fight with your sibling? And what remains the obvious cause always?
  27. How often do you bang your TV remote in a day but still do not change the cell? Wondering. Right?
  28. Have you ever tried giggling for no obvious reason?
  29. Do you like people who give advice and sermons too often? Why or why not?
  30. What is your instant reaction when you know you have messed up something in front of others, say in a restaurant?

Weird questions to ask a girl

Are you looking for some unusual questions to ask a girl? Then, this list of weird questions is great for you to make up a perfect conversation that can go on for hours.

  1. How would you like to decorate your dream house?
  2. Do you interrupt in between when others talk about you?
  3. What is the most disgusting food that you have ever experienced?
  4. What is your weird pet name that nobody knows?
  5. Name a few things that you will never buy?
  6. Do you dislike things that others like? Why?
  7. What’s the embarrassing stuff on social media these days?
  8. What will you never tolerate in your household?
  9. Can you imagine your life without a loving parent?
  10. Will you appreciate the success of your enemies? Why or why not?
  11. How will you resolve disagreements with your parents?
  12. What strange gift have you received on your 18th birthday?
  13. Have you ever been polite to someone when you felt like banging their head onto a wall?
  14. Do you check your whatsapp messages every one minute? How often then?
  15. Do you remember any immature thing that you do quite often?
  16. What is your weird fear that you are aware of but can’t let go?
  17. What are the new fashion trends for girls that are getting widely accepted in our society?
  18. Would you mind living in a conservative society? Why or why not?
  19. Do you donate to charity?
  20. How do you spend your Sunday evenings?
  21. Are you proud of your cultural heritage and traditions?
  22. Do you think that people should stop doing things that go against the law?
  23. How do you conquer your insecurities about your closest relationships?
  24. Has anyone told you that you look beautiful and stunning today?
  25. What are your views on ‘crossing limits’ in a relationship?
  26. How often do you go to a hair spa?
  27. With whom do you visit shopping malls?
  28. What is your best buy till date?
  29. How do you celebrate your parents’ wedding anniversary? Do you make them feel special on their big day?
  30. What funny thing did you do recently? Describe

Weird questions to ask your friends

Nobody wants to be around boring friends. Right? So you can use some weird questions to ask your friends and bust the monotony that appears after being with each other for a long time.

These questions are random, strange, and they may look at each other to come up with the best possible answer.

Some good questions to add to the list are:

  1. Do you wish to see the air? Mind Boggling right?
  2. Why are hot dogs named in such a way? Does it look like a dog?
  3. Describe your weird smell that you would never wish to sniff again?
  4. How many unwritten rules and norms do you have in your workplace? Do you follow them?
  5. How many medium sized pizzas can you gobble in 10 minutes? 
  6. What crazy challenge did you win till date? Describe
  7. Do you like cheese or butter?
  8. What is your favorite TV show that is crazy and weird but you still like it? 
  9. What rules should never be a part of a healthy society?
  10. Tell us about a weird and embarrassing thing that you’ve ever worn in a public place?
  11.  What’s a weird thing that a neighbor has done in your front door?
  12. How many times in a day do you comb your hair?
  13. Can you spend two hours looking at the wall clock in your bedroom without blinking your eyes?
  14. How many ducklings can a duck give birth to? Have you ever thought of it?
  15. Have you ever fallen from a horse’s back? Did you get hurt?
  16. How will you react if you suddenly see a big crocodile in your front door?
  17. Can you remember any real life person who looks like a famous fictional character that you enjoyed seeing being a kid?
  18. How much time would you take to eat your food, if you are sitting and eating at a community lunch?
  19. Have you ever been a part of a bachelor’s den? What crazy things people do there? Can you share your experience with us?
  20. Have you ever tried dismantling your smartphone?
  21. What’s the weird thing you do when nobody is watching you?
  22. Have you ever tried to play the role of your mother at home, at least for a day? Why or why not?
  23. Do you like conventional small talks or big, serious conversations when you’re with your best friends?
  24. Have you ever been bullied badly by your friends? When?
  25. How many times did you use public toilets without flushing it?
  26. Have you ever tried counting rice served on your plate? Why not try out one day? Right, friends?
  27. Who makes you laugh very often?
  28. What’s the best thing about the rainy season?
  29. How awesome ice cream should be? Any ideas
  30. Have you ever sung a karaoke song?

Weird questions to ask people

When you plan to ask odd and bizarre questions to people, be sure to get some weird answers in return. You will burst into laughter and the conversation will be a memorable one.

A good question can always be a good conversation starter as it makes the chit-chat interesting and people would like to continue with it for some time.

The list goes like this

  1. Do you count your missed calls?
  2. Which dress will you never mind repeating thrice a week?
  3. Have you ever travelled in a train without a ticket? When?
  4. How many times do you say ‘thank you’ and ‘sorry’ in a week? Have you ever counted it?
  5. What weird qualities do you possess that amuses others?
  6. Are you good at remembering things on the spot?
  7. What do you say to others quite often?
  8. Are you obsessed about looking in a mirror quite often? Why?
  9. Can you climb 500 stairs everyday as a regular exercise regime? Is it possible for you?
  10. Who admires you very often? Do you like it?
  11. When was the last time you screamed badly at someone? Why did you do it?
  12. How many times do you stop your car and take a break while you are on a long drive?
  13. What is the best form of exercise? Why?
  14. If you could change the color of your eyeballs, what color would it be and why?
  15. Which animal is friendlier as a pet – dog or cat?
  16. What will happen if a person wants to live an unruly life? Will it damage the society as well?
  17. If you are made a teacher for a day in a primary school, which subject will you prefer to teach and why?
  18. Tell us something about your least favorite mode of transport? Why is it so?
  19. Whom do you tell a lie quite often? Why?
  20. Have you ever apologized for a mistake that you’ve not committed? Why did you do so?
  21. What thoughts can make you feel relaxed and at peace with yourself quite easily?
  22. If you’re given a chance to transform yourself to an animal, which animal would it be and why?
  23. Have you ever found yourself without a wallet while paying money to someone?
  24. Are you a forgetful person? In what ways
  25. You have only five minutes to pick up groceries from a provision store. What will you buy?
  26. Are you happy the way you are or would prefer to change something, if given a chance?
  27. How many times have you fallen from a cycle when you were a child?
  28. Do you still love to fight with pillows with your sibling?
  29. Do you think you’re good enough or you try to achieve something more?
  30. When was the last time you had stomach pain?

Weird questions to ask your boyfriend

A hangout with a boyfriend may become monotonous if you do not have enough topics to talk about. 

Why not try out these weird questions that may appear silly yet helps to know each other well. You can expect some interesting answers on your way.

  1. If I tell you to describe your life in one word, what will it be?
  2. Do you know how many people do not like you?
  3. If you try to fail and succeed in return, will you be happy or sad? Why?
  4. Do you sleep walk?
  5. How many mosquitoes have you killed by now? Indeed a good counting exercise. Right?
  6. Why do we sleep? What will happen if we stay awake for a month?
  7. Have you ever had a bad haircut?
  8. When was the last time someone misbehaved with you? Do you still remember the incident clearly?
  9. Have you ever violated traffic rules? When and why?
  10. If you have a chance of marrying a celebrity, who would you marry and why?
  11. How many hours can you spend inside a swimming pool? Would you like to try it once?
  12. Have you ever fallen asleep while watching a movie?
  13. Which dairy product do you like the most and why?
  14. If you are told to choose a breakfast to be eaten for the entire month, what will you choose and why?
  15. How many hours can you spend without looking at your smartphone?
  16. How can you catch a thief who is trying to escape from your house?
  17. What’s the best way to pay attention to others?
  18. Would you mind if your girlfriend encroaches your personal space?
  19. What private things do you never mind doing with your girlfriend?
  20. Have you ever seen a weird TV show sitting with your mom and dad? Which show was it?
  21. Has anyone caught you doing an embarrassing thing recently?
  22. When was the last time you had a fever?
  23. What type of a girl will you marry?
  24. What are your thoughts on ‘kissing in public places’?
  25. Has anybody ever challenged your beliefs? 
  26. Are you too involved with something? What is it?
  27. If you are given a chance to pick up any job, what will it be and why?
  28. Who is the most liberal person in your life?
  29. What’s a common thing that people say about you?
  30. Has anyone ever considered you a nerd? Why?

Weird questions to ask your girlfriend

This list of weird questions to ask your girlfriend is a good fit for any occasion. If her answers vary from what you feel about it, then it doesn’t mean she is wrong, but indeed different from you.

  1. What makes you feel worse about yourself? Why?
  2. How many new dresses do you buy in a month?
  3. What’s one thing that your friend does for fun but you don’t?
  4. If someone tells you that they will give you a lifetime supply of anything that you like, what will that be and why?
  5. Are you popular for something amongst your friend circle? What is it?
  6. Will you be comfortable with a long distance relationship?
  7. Do you have a rule book of your own?
  8. Have you ever tried to write erotic poems for your boyfriend?
  9. Have you ever faced a broken relationship? Did you do anything to save it?
  10. What’s your definition of an attractive man? Clean shaven or a full beard type?
  11. Do you think we can make a good couple duo in whatever we do? Why?
  12. Will you be happy with me if you come to know that I have lost my job?
  13. How will you survive on a deserted island? Do you think you will manage the challenge fair enough?
  14. Can you remember your high school English teacher?
  15. Do you have matching shoes with all the dresses that you have?
  16. Does a woman play a vital role in a relationship? How?
  17. What couple goals will you set with your hubby when you marry?
  18. What difference do you find in your life now than what it was 5 years ago?
  19. Are you still in touch with your ex-boyfriend?
  20. Which funny movie have you watched recently that made you laugh whenever you thought of it?
  21. Did you ever had an unprotected sex?
  22. How good are you with money matters? Do you make a budget for your monthly expenditures?
  23. Do you think a man and a woman should split the cost of running a household?
  24. What do you usually eat as the last meal of the day?
  25. If you could erase certain moments of your life, what would it be and why?
  26. What bad habit of your partner do you hate the most?
  27. How often do you sing and dance? Or Is it you don’t do it at all
  28. Do you fantasize about sex and intimacy with your partner?
  29. Has anybody ever cheated on you? Who and how?
  30. Why can’t honesty be the best policy?

Weird questions to ask someone

Some funny and silly questions that can be asked to someone and can be included in your bucket list are:

  1. How often do you see your wrist watch if you know you’re getting late for something?
  2. Do you forward viral videos to your friends?
  3. What inanimate objects are you fond of?
  4. How well do you start a conversation with a lot of people looking at you?
  5. When was the last time you had lots of fun?
  6. Which body part of yours do you hate the most and why?
  7. If animals could talk, what would they have told you?
  8. Can you pick up a line with a boring conversation and make it exciting?
  9. What random questions to ask a guy who is sick and lying on a hospital bed?
  10. Tell us something about your weird sleeping position?
  11. Do you like to be a part of interesting conversations on sex and romance?
  12. What interesting questions will you ask a girl who is about to get married soon?
  13. Tell us the silly questions your high school teacher asked you 10 years ago? Do you still remember them?
  14. Have you ever caught someone shoplifting in front of you?
  15. Do you own smelly socks?
  16. Are you keen on wearing torn jeans while hanging out with friends? Why?
  17. How many times have you swallowed a toothpaste while brushing your teeth? Have you counted it?
  18. Do you respond to silly questions asked by your 3 year old toddler?
  19. Have you ever picked up a fight with a policeman in your life? When and how?
  20. When was the last time you had a loud shout while roaming around a high street?
  21. How many funny questions can you ask someone in one minute?
  22. Have you ever faced humiliation in front of many people? How did you feel about the incident?
  23. Did you ever fall in love with a stranger?
  24. Can you stay with someone under the same roof for 24 hours whom you do not know at all?
  25. What are your dating goals for this month?
  26. Have you ever searched weird things on Google?
  27. What did you do with your first month’s salary?
  28. How many times in a week do you masturbate just for fun? Quite unexpected but an obvious question. Don’t you think so?
  29. What are your three strengths that make you different from others in your family?
  30. Have you ever seen a fight between a polar bear and a group of penguins? Do they fight at all? Any ideas?

Weird questions to ask your crush

Are you eager to know whether they’re right for you? These interesting questions can be a perfect blend of fun and deep thinking that enables your partner to kick start a great conversation topic that can go on for a long time.

  1. What did you do for the first time to get your crush’s attention?
  2. How many times in a day do you shower?
  3. How often do you think about me in a day?
  4. What kind of sports fascinates you the most?
  5. Do you know how your parents got married?
  6. Can you sit gazing at the moonlit night sky for hours?
  7. Do you love the serenity of the night? Or does it scare you?
  8. What are your views about being brought up in an extended family? 
  9. Can joint families enhance family bonding? How and why?
  10. What is the last horror movie you’ve seen that amused you a lot and did not scare you at all?
  11. Are your parents happy about your accomplishments?
  12. Have you ever lost sight of an important issue? Why and how?
  13. Has anyone ever given you a killer look ever? Would you mind telling me something about it?
  14. Have you ghost written love letters for your friend? How was the experience?
  15. Who chides on you quite often and why?
  16. What old memories of your childhood do you still remember clearly?
  17. Who taught you at home when you were a child?
  18. Would you like to relive any part of your past life? Why?
  19. If you win a lottery someday, will you share the prize money with me?
  20. Do you seek permission from your parents if you’re going to pursue something very important in life?
  21. What are your views about serious couple fights?
  22. Has anything improved in your life over the last 5 years?
  23. If I tell you to ask me 20 questions, what will they be?
  24. What laptop brand do you carry for work?
  25. Who makes you feel appreciated and loved always? Is it me or somebody else?
  26. If someone fights with you unnecessarily, will you continue in a similar way or stop to maintain peace around?
  27. How many fan followers do you have on Instagram?
  28. Who is the first one who wishes you first on your birthdays?
  29. Did you learn anything about the culture and heritage of other countries when you travelled abroad?
  30. How do you keep yourself so fit and fine? What’s the secret?

Weird questions to ask Alexa

Alexa has the power to amuse and entertain you when you are feeling super bored and do not know what to do next. 

Asking weird questions to Alexa can beat boredom and bring a good dose of laughter.

  1. Alexa, start counting from 1 to 100
  2. Alexa, why does B come after A? Any ideas?
  3. Alexa, what should I order today for dinner?
  4. Alexa, Can I survive only on coffee for a week?
  5. Alexa, How are you today?
  6. Alexa, do you think I should marry now?
  7. Alexa, how can you help me sleep well?
  8. Alexa, do you know how to solve trigonometry?
  9. Alexa, do you think ghosts exist?
  10. Alexa, how many times do I visit the toilet in a day? Any ideas?
  11. Alexa, can you call mom now and see what she’s doing?
  12. Alexa, what is your weight?
  13. Alexa, do you know my neighbors?
  14. Alexa, which is your favorite pet/
  15. Alexa, can you give me some water now?
  16. Alexa, how well do you sing? Can you sing now?
  17. Alexa, who takes care of you when you get sick?
  18. Alexa, do you get headaches?
  19. Alexa, what should I buy from Amazon fresh today?
  20. Alexa, do you know my father?
  21. Alexa, can you make a pizza for me?
  22. Alexa, will you marry me?
  23. Alexa, can you play fetch with Tommy?
  24. Alexa, what are your future plans?
  25. Alexa, can you make weird sounds?
  26. Alexa, chicken roll please?
  27. Alexa, can you bark like a dog?
  28. Alexa, who is your best friend?
  29. Alexa, what’s the purpose of human life?
  30. Alexa, what’s your favorite color?

Weird questions to ask yourself

Sometimes asking oneself some out of the box questions can be really fun. You may wonder for a while before coming up with the best answer.

  1. How well can I sing a Christmas carol?
  2. Will I ever forgive someone who sin against me?
  3. What will be my dream holiday destination?
  4. Do I nag a lot and so people do not like me?
  5. What can I buy for my next birthday?
  6. Can I ever own a Ferrari?
  7. Am I grateful enough for what I have?
  8. What can agitate me quickly?
  9. What interesting questions can I ask a guy when I meet him for the first time?
  10. Can I do something productive for my community? 
  11. Why do I dislike undisciplined people?
  12. Can I give a yellow rose to my fiancée instead of red?
  13. Why do people say that I am haughty? Am I really so?
  14. What can I name my new private jet, if I ever have one?
  15. How many syllables are there in my name?
  16. What will I do if I don’t sleep one night, just out of choice?
  17. Do I have a catchphrase?
  18. How do I keep my temper in control? Is it really necessary?
  19. How often do I think about my future and why?
  20. Am I living a happy life?
  21. Can I live one night with the Pharaoh?
  22. If I can eliminate one of my weaknesses, what will it be?
  23. How do I want to be remembered when I die?
  24. What is my preferred sleep position?
  25. What guilty pleasure will I never give up and why?
  26. How often do I paint? What do they look like?
  27. Should I stop buying unnecessary stuff that I often do?
  28. Should I avoid conflicts and disagreements with my office colleagues?
  29. What bad habits should I change now? Why?
  30. Should I keep doing random acts of kindness whenever possible?
  31. Who is my partner in crime and why?
  32. Will I talk to an outsider in a movie theatre?
  33. What can make me sad easily? Why?
  34. How about owning an animal farm?
  35. Why do people give only red roses on Valentine’s Day?
  36. Why do I hate changing my remote control battery when I know I need to do it?
  37. Can I spell the longest word in the English dictionary?
  38. How many times in a day do I check my whatsapp messages?
  39. What can I buy for my mom today?
  40. Why do married people fight more than those single people out there? Do I really know the answer?

Weird questions to ask your partner

Some random questions that are weird, odd, and out of nowhere are a must-have to ask your partner.

  1. What’s the future of a long distance love?
  2. Do you have a messed up story to share with me?
  3. Do you think you have enough wealth to live a happy and secure life?
  4. Has anyone caught you doing something awkward? What was it?
  5. Do you like seeing music concerts?
  6. What is your favorite ice cream flavor?
  7. How many times have you changed your car in the last 5 years?
  8. Have you ever stolen money from your father’s pocket? How often?
  9. How about counting steps while walking? Have you ever tried doing it?
  10. Can you sleep with your eyes wide open?
  11. Tell me something about your last cruise journey.
  12. What is your lucky gemstone?
  13. Did you like playing treasure hunting when you were a child?
  14. What have you lost and found again recently?
  15. Have you ever lost your phone charger?
  16. How many shampoo bottles do you need in a month?
  17. Have you ever taken someone else’s handkerchief to wipe your nose?
  18. What are your preferred possessions that you’ll never share with anyone?
  19. Have you ever made an honest confession to anyone?
  20. Why do people steal shampoo bottles and toothpaste from hotel rooms? Any ideas?

Weird questions to ask your parents

Have you ever tried asking weird and silly stuff to your mom and dad? If not, you can give it a try because you will get some amazing answers.

Asking weird questions to parents are good conversation starters that can help you spend quality time with them, making good family bonding possible to savor for life.

  1. Am I your favorite kid?
  2. Do you drive over speed limits? Were you ever caught by the traffic police?
  3. What fond memories do you have of the city you grew up in?
  4. What makes you feel that your kids have become mature and responsible?
  5. Are you happy with my career accomplishments?
  6. Who do you think is good at sports? Me or my sibling?
  7. What behavior of mine hurts you the most?
  8. When was the last time you yelled at me for no reason?
  9. Did you ever have big issues with your parents while growing up? Why?
  10. Do you remember the first day of college? How was it?
  11. What is your favorite hobby? Why?
  12. Where did you and mom/dad meet for the first time? How was the meeting?
  13. Can you remember the first gift your mom/dad gave you when you got your first job?
  14. How well do you relate with the mindset of the young generation? Do you think it’s different from your generation? Why or why not?
  15. What is the best thing that I and my brother/sister gave you till date?
  16. Do you think you have lived your life the way you wanted? Can you tell me about your deepest regrets?
  17. Do you cry seeing an emotional movie?
  18. Are you a spiritual person?
  19. Have you tried giving up your bad habits? Were you successful in your attempts?
  20. Is it okay for me to marry an older girl/boy? Will you accept the union gladly?

Parting words from ‘The Pleasant Conversation’

Sometimes interesting conversations need great questions to pick up lines of communication and a deeper understanding of one another.

When you get interesting answers to such weird and crazy stuff, you may feel fresh and rejuvenated to spark good conversations that can bust monotony and spice up your leisure time fully.

So, by now you have many such handy questions that can gear up good connections and develop better social relationships.


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