What’s the best conversation starter? Asking a question, of course! This is a great way to, first and foremost, figure out the humor and the surface-level personality of the person you’re talking to. The last thing you want to do is ask a question that might push some buttons or cross a line. 

So whether you’re looking for great interview questions, interesting questions as a way to break the ice in the workplace or at school, or funny and weird questions to ask the guy or girl you’re on a date with, we’ve got you covered. These will be sure to get you an answer that you might not have expected. 

Fun/Funny Questions To Ask A Person 

1. If you had to choose an animal to help you win a fight, what animal would it be?
2. The Internet is a mix of everything: good, bad, scary, and fun. What would you say is the worst thing about it?
3. If you could make one rule that everyone had to follow for one day, what would the rule be? 
4. What is the funniest thing you’ve seen a stranger do in public? 
5. Would you ever eat ice cream with your hands?
6. Would you say you enjoy sarcastic and deadpan humor, dark and self-deprecating humor, or slapstick and parody kind of humor? 
7. What was your favorite color as a kid? Could you imagine only wearing that color for the rest of your life? 
8. If you could play a minor character in your favorite movie, what would your name and job be? 
9. Do you have any funny or secret talents you’d be willing to share? 
10. If a person you’ve met only once before asked you to pack a bag and go on a fun and spontaneous adventure, would you go? 
11. When was the last time you had a good laugh? 
12. What is the craziest thing that has happened to you while at school? 
13. Do you have any fast food horror stories? 
14. What do you think people will be nostalgic for in 20 years? 
15. If you could ask me one funny question, what would it be?
16. Have you ever not worn underwear?
17. Have you ever kissed someone at school?
18. Have you ever kissed someone at work?
19. Have you ever been to a makeout party as a kid?
20. Who is your idol?
21. Who is a person that you’d want to torture for the rest of your life?
22. What’s the craziest thing you’ve done in public?
23. Have you ever walked in on your parents?
24. What’s one embarrassing thing you saw your parents doing?
25. What’s your most embarrassing story from childhood?
26. Did you ever pee your pants as a kid?
27. Did you ever go poop in your pants as a kid?

Funny Questions To Ask A Friend or Best Friend

1. What does our friendship look like?
2. What’s one word that describes our friendship?
3. What’s the craziest memory you want our friendship to share?
4. If we had a fistfight, who would win?
5. What’s one swear word that best describes me?
6. What’s one memory that you never shared with me?
7. What’s one thing that you held back telling me that you wish you could say?
8. If we helped each other cheat on a test, who would help who?
9. Would you copy a test’s answers from me?
10. Do you think I would copy test answers from you?
11. Describe our friendship with one STD.
12. Tell me one STD you think I might have.
13. If I failed a driver’s test, what part would I fail?
14. Am I good a driver?
15. Would you trust me to drive blindfolded?
16. How many beers do you think I could drink?
17. How long do you think my hair can grow?
18. What’s one thing you wish we knew right now?
19. What’s one thing you wish we knew a year ago?
20. Who is your favorite celebrity?
21. Who is your favorite celebrity crush?
22. What’s one memory that you’ve never told me?
23. If we played truth or dare, what’s a dare you would ask me?
24. If we played truth or dare, what’s a truth you would ask me?
25. What’s your favorite smell?
26. If you could be an animal, what would it be?
27. If you could have one body limb removed, what would it be?
28. In a fight between Superman and Batman, who would win?
29. Who’s the bigger party animal?
30. Who would stay alive longer in a zombie apocalypse?
31. What weapon would you choose in a weapon fight?
32. Who is the rudest person here?
33. How much do we think elephants eat?
34. What’s the most boring sport?
35. If you could be a fruit, what fruit would it be?
36. If you could be a body part, what body part would it be?
37. What instrument is the most annoying to you?
38. If you could be any fictional character, who would it be?
39. What’s the most useless word in the dictionary?
40. What superhero would you be if you could be any?
41. What’s your least favorite holiday?
42. What’s your favorite thing to do in your spare time that you’re embarrassed about?
43. If you had to lose an arm or your nose, which would you choose?

Funny Questions To Ask As An Ice Breaker 

1. What is a fun fact you like to tell people about yourself? 
2. If you were in the middle of a zombie apocalypse and you could only use an item from a bathroom to protect yourself, what item would you use?
3. Do you eat or drink soup? 
4. Let’s say you’re at the grocery store. What three items are you checking out that would make the cashier laugh or question you and your purchases? 
5. What body part do humans have that you find funny? 
6. If animals could talk, which animal do you think would maintain great conversation? 
7. If you could ask the Queen of England one super silly question, what would you ask? 
8. Do you prefer your easter eggs to be plastic and filled with little candies or to be real, hard-boiled eggs you can peel and eat later? 
9. What is a funny thing you’ve witnessed recently? 
10. If you could morph two animals, which ones would you choose and what would it be called? 
11. Can you fold a fitted sheet? 
12. Let’s talk about toilet paper. Over or under? 
13. If you could be any animal, what would you be and why?
14. What living person, non-family member, do you admire the most? 
15. If you were abducted by aliens and they telepathically asked you who you wanted to bring with you on their spaceship, what 3 people would you ask them to pick up? 

Funny Questions To Ask The Guy or Girl You Have A Crush On

When it comes to crushes and dating, sometimes you just have to go big with an ice breaker question to get the conversation going. 

1. What is the funniest or weirdest thing that has ever happened to you on a first date? 
2. If you were forced to detach a body part, which one would you choose?
3. What is the funniest joke you know and tell at parties? 
4. Do you still sleep with a stuffed animal? 
5. If you could be any mythical creature what would it be and why? 
6. What is your favorite thing to do after a long day? 
7. If someone asked you to go to the website you most frequently visit, would you be embarrassed or happy with your answer? 
8. What is the last question you searched on Google? Read it out loud. 
9. Do you know any funny pick up lines? 
10. If you were able to meet any celebrity, dead or alive, who would it be and what is something you would want to have a conversation about? 
11. What is a funny thing you believed as a kid? 
12. If you were a pizza topping, what would you be?
13. If you could be a fly on the wall, where would you land?
14. When you were a kid, what did you want to be when you grew up? 
15. A person from the future has traveled back in time to answer one question for you. What is the question you ask them? 
16. Have you ever had to use the restroom outside?
17. What’s the worst thing that’s happened to you at the gym?
18. Who do you least look like (celebrity wise)?
19. Who do you most look like (celebrity wise)?
20. What’s one word that doesn’t describe you?
21. Who would you fight in a boxing match?
22. What food would you prefer to throw up?
23. What food would you never feed to a horse?
24. What food would you eat for the rest of your life?
25. What would you rather have in your bed, a horse, or a goat?
26. Who would you want to make a child with, Oprah or O.J.?
27. What should we do when we’re old?
28. When should we send our kids out of the house?
29. Who is a celebrity relationship that you want our relationship to be like?
30. Who is going to marry us a pastor or a priest?
31. If you could die my hair any color, what would it be?
32. If we had an argument and couldn’t get over it, who would you ask to mediate the situation?
33. Where’s the craziest place you want us to kiss?
34. Where’s the craziest place you want us to make love?
35. What’s the craziest memory you want us to share as a couple?
36. Who would be your best man?
37. Who would be your bridesmaids?
38. What’s one movie that you want our relationship to be like?
39. What’s one book that you want our relationship to be like?
40. Fifty shades of grey or the notebook?

Fun/Funny Siri Questions  

1. What does Siri mean?
2. Are you a person? 
3. Can you dream? 
4. What is your favorite animal?
5. Do you believe in ghosts? 
6. How much wood could a woodchuck chuck if a woodchuck could chuck wood?
7. Who you gonna call?
8. What is your best pick up line? 
9. What came first: the chicken or the egg?
10. Do you want to build a snowman?
11. Red pill or blue pill?
12. Do aliens exist?
13. Can you tell me a joke? 
14. What kind of bear is best? 
15. Can you beatbox? 

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Do you like answering deep questions about life and the universe or personal questions about your life and your secrets? Or do you like answering questions that are more surface level?