There might be various reasons why you’re looking for some hilarious funny questions to ask a guy.
You may have met someone charming and want to strike up a discussion, but are unsure what funny questions to ask a guy to begin a lengthy and pleasant conversation.
You’re not sure how to start a conversation with an unknown handsome guy. There is apprehension and uncertainty about whether or not the other person will be interested in conversing.
Certain inquiries may lead to a long and engaging conversation, but asking the incorrect question in the wrong setting might completely derail the topic.
Fear of the consequences or uncertainties may sometimes keep your genuine feelings hidden and undermine your self-confidence. As a result, you may find yourself asking questions that give the other person a poor opinion of yourself.
Certain fun questions to ask a guy are included below under several categories that may help you start and maintain a pleasant discussion with the other person, as well as develop your connection with them.
Table of Contents
Best Funny Questions to Ask a Guy
In this category we have arranged for you some of the best funny questions to ask a guy. These questions are really the best ever hilarious questions you can ask a guy to initiate or prolong the boring conversation.
1. Why is it that round pizzas come in square boxes?
2. What would you do if you won a million dollars?
3. How many beers do you think I’d be able to consume?
4. Have you ever gone to a corner store and stolen a candy bar?
5. How long do you think you’d survive in a zombie apocalypse?
6. If you can still remember, what are your funniest childhood memories?
7. Have you ever gone a day without wearing underwear?
8. What is it that you keep wanting to smell despite the fact that it doesn’t smell particularly good?
9. What are the crazy adventures you want to try in your life?
10. Have you ever fallen off your bike in front of a huge crowd?
11. What is the best Wi-Fi name you have seen in your entire life?
12. What are three items you might purchase at the grocery store to get strange looks from the cashier?
13. Do you sometimes hear certain voices in your head, too?
14. Can you show me the hidden apps in your phone?
15. Have you ever been caught cheating on a test?
16. If I will fail a driver’s test, in which part will I fail?
17. Has someone caught you dancing in front of the mirror?
18. Where was the most embarrassing place you have ever farted?
19. What would you do if you only had 24 hours to live?
20. What’s the most embarrassing moment in your entire childhood?
21. What do you think is the worst thing that a person can put on their bio on a dating app?
22. If you could remove one color in the whole world, what would it be and why?
23. If you could ask me a funny question, what do you think would it be?
24. What secret conspiracy would you like to actually start letting other people know?
25. If you were to be banned from your local library, what would be the reason?
26. Have you ever made a prank call to someone you don’t know?
27. What’s one thing your dogs could say that would completely ruin your image if they could talk?
28. If you could have a superpower, what would it be?
29. What is the silliest thing you’ve ever seen a stranger do in public?
30. What music instrument has the most annoying sound to you?
31. Have you ever been in a car crash where you were at fault?
32. What has been the strangest thing a visitor has done at your home?
33. Do you believe it is possible to inflate a balloon when underwater?
34. What color would you like if you had to eat a crayon straight from the box?
35. What has been the funniest or strangest thing that has happened to you on a first date?
36. Have you ever driven someone else’s car without first getting permission?
37. If you could choose any animated character, who would it be?
38. Which of your body parts do you wish to change?
39. Where would you like to time travel: back to the past or to the future?
40. Can you tell me the most hilarious joke you’ve heard?
41. Have you ever succeeded in making one of your parents cry?
42. Do you think the sea is salty because the shore never waves back at it?
43. Have you ever consumed so much alcohol that you passed out?
44. What’s your preference: to be buried or be cremated?
45. What’s the craziest thing you’ve ever done after getting really drunk?
46. Did you once forget to bring your wallet when you’ve been scheduled to pay for a meal?
47. Which person do you know that totally reminds you of a character in a TV show or movie?
48. Which species would be the rudest if all animals could talk?
49. What do you think your last meal would be if you were on death row?
50. Have you experienced going skinny-dipping before?
51. What is the worst possible name you might give your child?
52. What do you call a girl named after her mother if a boy named after his father is called junior?
53. Do you have a habit of going for a walk while sleeping?
54. Where did all the money go if the whole world were in debt?
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Random Funny Questions to Ask a Guy
In this category we have arranged for you some of the random funny questions to ask a guy. These are some light hearted questions you can ask randomly on the go.
1. What music would you like to be played at your funeral?
2. Have you created a rumor about yourself just to be the talk of town?
3. If life is a video game, what cheat code would you want to use most?
4. What would be the outcome if the government decided to make everything illegal?
5. Would you rather be forced to wear shoes every second of your life or never be able to wear shoes again?
6. Which aspects of mine do you admire and which do you despise?
7. Who do you wish you could torture for the rest of your life?
8. In all honesty, what are some of your guilty pleasures that you are willing to admit?
9. What would you do if you could replace all of the grass on the planet with something else, and why?
10. In terms of appearance, which athlete do you believe most closely resembles you?
11. Have you ever been called out at school for wearing something embarrassing?
12. What will people be nostalgic for in 500 years?
13. What’s the worst tag line you can think of for a wart removal cream company?
14. Can you tell me one memory that you’ve never shared with me?
15. Have you ever approached a stranger and said something that later turned out to be your best friend?
16. How many ants would it take to lift an elephant?
17. What do you think the first person to milk a cow was actually trying to do?
18. What would you leave me in your last will and testament right now, if you were to die?
19. What’s the weirdest thing you’ve given someone as a gift?
20. If we were to have a boxing match, who do you think would win?
21. What kind of food would you never offer a tiger?
22. Have you ever had a teacher call you in class when you had no idea what was going on?
23. What would your friends and family think if you were arrested without explanation?
24. Where does prune juice come from if prunes are dried plums?
25. What is the one thing about yourself that you would like to change?
26. What’s the most amusing thing you’ve seen recently?
27. What is the funniest name you have ever heard in real life?
28. Have you ever come into contact with human remains?
29. Do you ever cry while watching an emotional film?
30. Who would help who if we were to help each other cheat on a test?
31. Have you ever failed to prepare for an exam before the day you were supposed to take it?
32. How do you sleep, with your eyes open or closed?
33. If Donkey Kong is a monkey, not a donkey, why was he given that name?
34. Which movie would you want it to be if your life was a movie?
35. Would you brag about your spontaneous acts of kindness?
36. What would you do if you could become invisible for a day?
37. How long has it been since you laughed out loud?
38. Which type of clothing do you no longer want to wear but can’t get rid of?
39. In a zombie apocalypse, who will last the longest?
40. Has someone ever made a comment on how loud you sing in the shower?
41. What would peanut butter be named if it wasn’t called peanut butter?
42. Have you ever dreamt about one of your friends?
43. What kind of food would you eat if you could eat one for the rest of your life?
44. Where was the worst date you’ve ever experienced?
45. What’s one thing you wish we knew five years ago?
46. What do you believe is the most horrible way to die?
47. How would you sum up the internet in two sentences?
48. As a child, what was your favorite game to play?
49. Which app on your phone do you use the most?
50. What excuse have you recently used to avoid doing something?
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Funny Questions to Ask a Guy to Make Him Laugh
Below we have arranged for you some of the funny questions to ask a guy to make him laugh. These are quite hilarious questions to make your guy bend on his stomach.
1. What was the last book or series you wished you could live in?
2. What would you do with the money if you won a lottery?
3. What is the strangest Amazon purchase you’ve made or nearly made?
4. If you were a dog, which breed would you want to be?
5. What sport do you think is the most boring watch?
6. Can you describe our friendship in three words?
7. What color would you pick, if I let you dye my hair any color?
8. Have you ever lied about your age in order to gain access to a bar or a nightclub?
9. How many zombies do you want to kill when the time comes?
10. What’s the best inside joke you’ve ever heard?
11. Before there were dictionaries, where did dictionary makers search for the definitions of words?
12. Do you have a habit of saying absurd things while you’re sleeping?
13. Which celebrity friendship do you want to embody in our friendship?
14. Have you ever cried yourself to sleep because of something that happened that day?
15. What is it that everybody seems to be doing that makes them look stupid?
16. Have you already been forced to share a bed with a person you didn’t want?
17. Have your parents ever found you trying to leave the house without permission?
18. What movie’s plot changes entirely only by changing one letter in the title?
19. Why do we refer to an alarm clock as going “off” when it actually turns on?
20. What is the weirdest food combination people eat that you just can’t get behind?
21. If you could be a dessert, what would you be?
22. What’s the best joke you know and tell at parties?
23. Have you ever broken your friend’s bone in the past?
24. What do you think will the world be like if it will be filled with male and female copies of you?
25. If you could have dinner with any five people from history, who would they be?
26. Have you ever pretended to be sick when you were perfectly healthy?
27. What’s the best brand of alcohol you always look for and don’t buy when the groceries ran out of it?
28. How do you react when you find something intriguing?
29. If are to open a store, what are the things you would sell and what would be its name?
30. Who do you see as a hero in this world and why?
31. Have you slept in until 4 in the afternoon or later?
32. What the things that are okay to do occasionally but definitely not okay to do every day?
33. What would you do as a career if you could do anything in the world?
34. What law would you introduce if you had the chance to make one?
35. If you could ask the president one super silly question, what would you like to ask?
36. Have you ever lied to your parents about the thing you accidentally broke?
37. What are the two totally normal things that become really weird if you do them back-to-back?
38. What are the things you will do if your gender will be changed for a day?
39. What would you do or say if you had the attention of the whole world for twenty seconds?
40. If you were a laptop brand, which one would you be and why?
41. Have you ever laughed out loud that something you were drinking eventually came out of your nose?
42. What would you take with you if tomorrow you were required to evacuate and you only had time to grab 10 items?
43. What’s the funniest book you’ve just read recently?
44. What are the words you’d add to the dictionary, and what would be its definition?
45. What pizza topping do you like if you had to be one?
46. Have you ever attended a dance by yourself because you couldn’t find someone to accompany you?
47. What do you usually do with your shopping cart when you are already done with it at the grocery store?
48. What would your stage name be if you are famous?
49. Will you be humiliated or pleased if anyone asked you to go to the website you most often visit?
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Funny Questions to Ask a Guy You Like
Following are some of the funny questions to ask a guy you like. Seems like you are down for that guy so why miss the chance! Ask out these funny questions to entertain the interaction.
1. If you could be a fly on the wall, who would you want to listen in on?
2. If you were an artist, what would you paint on your first day?
3. If animals could talk, which would be the smartest?
4. What would be your weapon of choice in a zombie apocalypse?
5. Who would win in a fight between Superman and Batman?
6. Do you think cavemen had nightmares about cavewomen?
7. What sport would be the funniest to add a mandatory amount of alcohol to?
8. How many chickens would it take to kill an elephant?
9. What would you rather have; an arm that regenerates every month, or legs that grow back in every month?
10. What sound would be the scariest if you could hear it?
11. What fictional character do you think you are most like?
12. What superhero/villain would make the best therapist?
13. If you could be a fictional character, who would you be?
14. What instrument do you think is the most annoying?
15. What would you rather have to deal with: Have no nose, but have really good smelling fingers?
16. What is the worst/most annoying catchphrase?
17. If you could be in any movie, what would it be?
18. Which smells better, fresh-cut grass or bread baking in the oven?
19. What is one thing you would change about your daily routine?
20. What is one thing you wish could exist but doesn’t at the moment?
21. Who’s the most interesting person you’ve ever met?
22. What is the most useless invention of all time?
23. What song would you play if you were at a party?
24. Which would you rather win: The lottery or to be named employee of the month every month?
25. Would you rather walk around with a salad for a head or broccoli for arms?
26. What was the most embarrassing moment of your life?
27. If you could be any type of plant or animal, what would you be?
28. What was the worst or weirdest dream you ever had?
29. What is the funniest/craziest thing you’ve ever done?
30. What celebrity would you most like to switch lives with?
31. What is the most interesting place you’ve ever been to?
32. If you could take just one thing with you to a deserted island, what would you choose?
33. If you could have one superpower, what would it be?
34. If you could invite three people to dinner, living or dead, who would you invite?
35. What is the funniest joke you know by heart?
36. What is something that everyone looks stupid doing?
37. What’s the most ridiculous fact you know?
38. What’s the weirdest smell you have ever smelled?
39. What’s invisible but you wish people could see?
40. What is the sexiest and least sexy name?
41. What’s the most imaginative insult you can come up with?
42. What is the most embarrassing thing you have ever worn?
43. In one sentence, how would you sum up the internet?
44. What’s the best inside joke you’ve been a part of?
45. Where is the strangest place you’ve urinated or defecated?
46. If animals could talk, which would be the rudest?
47. What kind of secret society would you like to start?
48. What part of a kid’s movie completely scarred you?
49. How do you feel about putting pineapple on pizza?
50. What are the unwritten rules of where you work?
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Funny Questions to Ask a Guy on First Date
In this category we have arranged for you some of the funny first date questions to ask a man. If you are going out on a very first date so, why worry! We have listed these decent and funny questions to let the conversation go in flow.
1. What type of grocery store shopper are you?
2. What’s something that’s embarrassing, but shouldn’t be?
3. Be honest, how many hours a day do you spend on TikTok?
4. What’s a book you’ve never read but pretend to have read?
5. If you were an amateur wrestler/D-List superhero, what would your name be?
6. If your life was the “expectation vs. reality” meme what would the two pictures be?
7. Does being an influencer sound like heaven or hell?
8. What’s the cheesiest internet pop psychology advice that actually struck a chord with you?
9. What do you buy too much of but seem to never have enough of?
10. What was the worst middle school fashion trend you participated in?
11. Can you please tell me about your best worst school photo?
12. What’s a word you pronounced wrong your whole life?
13. Would you rather be TikTok famous or win a grammy?
14. If someone only saw your Spotify or Netflix accounts, who would they think you are?
15. If I pay for drinks, can I complain about my terrible roommate clogging the sink again?
16. Want to guess what my passive-aggressive coworker emailed me today?
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Weird and Funny Questions to Ask a Guy
In this category we have arranged for you some of the weird questions to ask a guy. Here we have enlisted some quite weird and awkward funny questions to make your conversation versatile.
1. What is the funniest corporate / business screw up you have heard of?
2. What movie would be greatly improved if it was made into a musical?
3. If peanut butter wasn’t called peanut butter, what would it be called?
4. What are some of the nicknames you have for customers or coworkers?
5. What would be the worst thing for the government to make illegal?
6. What would be the absolute worst name you could give your child?
7. What is the weirdest thing you have seen in someone else’s home?
8. What inanimate object do you wish you could eliminate from existence?
9. What mythical creature would improve the world most if it existed?
10. What’s the weirdest thing a guest has done at your house?
11. What used to be considered trashy but now is very classy?
12. Which body part do you wish you could detach and why?
13. What are some fun and interesting alternatives to war that countries could settle their differences with?
14. What is something that you just recently realized that you are embarrassed you didn’t realize earlier?
15. What would be the creepiest thing you could say while passing a stranger on the street?
16. What set of items could you buy that would make the cashier the most uncomfortable?
17. What two totally normal things become really weird if you do them back to back?
18. What would be the coolest animal to scale up to the size of a horse?
19. What would be the worst “buy one get one free” sale of all time?
20. If life were a video game, what would some of the cheat codes be?
21. If someone asked to be your apprentice and learn all that you know, what would you teach them?
22. What are some fun ways to answer everyday questions like “how’s it going” or “what do you do”?
23. You’re a mad scientist, what scientific experiment would you run if money and ethics weren’t an issue?
24. If you were arrested with no explanation, what would your friends and family assume you had done?
25. What are some things that are okay to occasionally do but definitely not okay to do every day?
26. Who do you know that really reminds you of a character in a TV show or movie?
27. What would be the best-worst name for different types of businesses?
28. What would the world be like if it was filled with male and female copies of you?
29. If the all the States in the USA were represented by food, what food would each state be represented by?
30. What movie completely changes its plot when you change one letter in its title?
31. First think of a product. Now, what would be the absolute worst brand name for one of those products?
32. Do you have any funny or secret talents you’d be willing to share?
33. If you could play a minor character in your favorite movie, what would your name and job be?
34. Would you ever eat ice cream with your hands?
35. What is the funniest thing you’ve seen a stranger do in public?
36. If you could make one rule that everyone had to follow for one day, what would the rule be?
37. The Internet is a mix of everything: good, bad, scary, and fun. What would you say is the worst thing about it?
38. If you had to choose an animal to help you win a fight, what animal would it be?
39. What’s your most embarrassing story from childhood?
40. What’s one embarrassing thing you saw your parents doing?
41. Who is a person that you’d want to torture for the rest of your life?
42. What do you think people will be nostalgic for in 20 years?
43. Do you think I would copy test answers from you?
44. What’s one thing that you held back telling me that you wish you could say?
45. What’s the craziest memory you want our friendship to share?
46. What’s one word that describes our friendship?
47. What living person, non-family member, do you admire the most?
48. If you could morph two animals, which ones would you choose and what would it be called?
49. If you could ask the Queen of England one super silly question, what would you ask?
50. What is the last question you searched on Google?
51. If you could be any mythical creature what would it be and why?
52. What is the funniest joke you know and tell at parties?
53. What is the funniest or weirdest thing that has ever happened to you on a first date?
54. What’s one movie that you want our relationship to be like?
55. Where’s the craziest place you want us to make love?
56. What’s the craziest memory you want us to share as a couple?
57. If we had an argument and couldn’t get over it, who would you ask to mediate the situation?
58. Who is a celebrity relationship that you want our relationship to be like?
59. What food would you eat for the rest of your life?
60. What’s the worst thing that’s happened to you at the gym?
Crazy and Funny Questions to Ask a Guy
Check the following crazy questions to ask a guy. Here we have got you some out of the box crazy questions to make your guy feel comfortable and frank.
1. Did your parents ever give you an embarrassing haircut?
2. What did you grow up believing about the Easter bunny?
3. What did you grow up believing about the tooth fairy?
4. What did you grow up believing about Santa Claus?
5. What’s something totally ridiculous that you believed as a kid?
6. What’s the stupidest way you’ve ever gotten hurt?
7. What did you do for your birthday parties as a kid?
8. What’s the worst gift you’ve ever received?
9. What’s your most embarrassing moment?
10. Who in your life has made you laugh the hardest?
11. Did your high school/college have any weird traditions?
12. Have you ever had a D.I.Y. project go wrong?
13. What’s the worst meal you’ve ever made?
14. What’s the best prank you’ve ever pulled?
15. Did you ever get detention in school, and what was it for?
16. When did you get drunk for the first time?
17. What was a movie you watched over and over again as a kid?
18. What was your best Halloween costume?
19. Which actors would play your parents in a movie about your life?
20. If you could be famous for any skill in the world, what would you pick?
21. If you could go for a beer with any celebrity, who would it be?
22. If you had to take a road trip with any celebrity, who would it be?
23. If you could marry any celebrity, who would it be?
24. If you could have a one-night stand with any celebrity, who would it be?
25. Which celebrity would you choose to be their VP?
26. Which celebrity would you most want to be stranded with on a desert island?
27. If we were forced to elect another celebrity to be the president, who would you pick?
28. What’s a completely non-sexual thing that turns you on?
29. What’s the most ridiculous myth about s#x you’ve ever heard?
30. What’s the least helpful “birds and bees” talk you’ve ever received?
31. How did you first learn where babies come from?
32. In your opinion, what’s a totally underrated s#x position?
33. If you had to live in any fictional universe, what would it be?
34. If you found $1,000 cash on the ground, what would you do with it?
35. Would you ever volunteer to colonize Mars, knowing you’d never return to Earth again?
36. Would you rather have 10 enormous dogs or 100 pet snails?
37. If you could be a contestant on any reality show, what would it be?
38. If you could transform into any animal, what would it be?
39. What’s your weapon of choice in a zombie apocalypse?
40. If you could only listen to one band for the rest of your life, what would it be?
41. What are you top three favorite movies that are so bad, they’re somehow good?
42. What’s the funniest book you’ve ever read?
43. When was the last time you laughed so hard you cried?
44. Who’s your favorite stand-up comedian?
45. What’s a TV show that routinely makes you laugh out loud?
46. What’s are the top three funniest movies you’ve ever seen?
47. What’s a TV show that people would be surprised to know you watch?
48. What’s the latest scripted show you binge-watched?
49. If you could rename any animal, what would you call it?
50. Would you rather have a baby giraffe or baby elephant as a pet?
Witty and Funny Questions to Ask a Guy
In this category you can find some of the witty questions to ask a guy. You must ask your guy these witty and funny question to let the conversation going smoothly.
1. Would you rather move like a kangaroo or a crab?
2. Would you rather have lobster claws for hands or squid tentacles for legs?
3. Would you rather have webbed fingers or webbed toes?
4. If you had a pet parrot and could teach it one phrase, what would it be?
5. What animal can you imitate the best? Which one should I do?
6. What would your pet name you if it could?
7. Would you rather roar like a lion every time you sneeze or howl like a wolf every time you yawn?
8. If they could talk, what do you think dogs would say?
9. Would you rather compete in a dance-off or a karaoke contest?
10. If you could host your own game show or TV competition, what would it be? Who would compete?
11. What’s an Olympic sport that doesn’t exist, but should?
12. If you could cancel one of your classes for a day, what game would you play with your class instead?
13. Would you rather have super strength in one hand or super vision in one eye?
14. Would you rather laugh every time you talk or always have to whisper?
15. What is the silliest theme for an amusement park you can think of? What would it be like there?
16. Would you rather have a rocket ship or a submarine?
17. If you could live life in any cartoon or comic book, which would you choose? Which character would you want to be?
18. Would you rather eat a giant candy cane or a giant chocolate pumpkin?
22. If candy were not an option, what should kids get while trick or treating?
23. You have $10,000 to spend on a Halloween costume. What would you be?
24. Which holiday would you celebrate every day if you could?
25. What would you do if I stole your Halloween candy?
26. If you could have a pet snowman for a day, what would you do?
27. Would you rather have a band of minions or fairies to do whatever you ask them to?
28. Which Disney character would you want to be your best friend?
29. What would your magician name be and what trick would you be known for?
30. If you could be the best in the world at something, what would it be?
31. What book or series did you wish you could live in?
32. If you could invent a holiday, what would it be?
33. What is the worst fashion decision you’ve ever made? Do you have a picture of it?
34. If you could make the ultimate sandwich, what would be on it?
35. What is your go-to movie when you need a mood boost?
36. What is one band or musician you would love to party with?
37. If you had a pet parrot, what would you teach it to say?
38. What is a food combination people eat that you just can’t get behind?
39. Who do you think will be playing on “oldies radio” in 30 years?
40. If you were famous, what would your stage name be?
41. What’s the funniest thing you’ve read recently?
42. If you opened a store, what would you sell, and what would be its name?
43. What food do you think would represent each U.S. state?
44. Have you or someone you know seen your doppelgänger?
45. What two “normal” activities would be really weird if you did them back to back?
46. What word do you want to be added to the dictionary, and what is the definition?
47. What is your favorite line from any movie?
48. Who is the one celebrity you would want to be friends with?
49. What celebrities would you want to play your parents in a biopic about your life?
50. Where is the coolest place you’ve ever pooped?
Flirty and Funny Questions to Ask a Guy
In this category we covered some of the flirty questions to ask a guy. These are some flirtatious and hilarious questions to make your guy fall all the way for you.
1. If you could be any kind of animal, which would you be?
2. What’s the most embarrassing thing you’ve ever said in a meeting?
3. If you could, would you go to outer space?
4. If you could meet any author, who would it be and why?
5. If you remember, what was your kindergarten teacher like?
6. How would your parents describe your personality?
7. Did you ever get in trouble at school as a teen and if so, what for?
8. If you could attend any celebrity wedding which would it be?
9. Which Hogwarts house do you belong in and why?
10. What cartoon character do you relate to the most and why?
11. If you could do any track and field event, what would it be?
12. Which was your first magazine subscription?
13. How many languages can you say “hello” in?
14. What’s the smelliest thing someone could put in the office microwave?
15. What was your most embarrassing moment from wearing braces?
16. Which is the best Ben & Jerry’s ice cream flavor?
17. What’s the best book-to-movie adaptation?
18. What’s the worst television reboot so far?
19. When you were a kid, what name did you give your favorite toy or stuffed animal?
20. Do you have a secret talent? Can you do it right now?
21. What is the best excuse for being late you’ve heard or used?
22. What TV show would you want to be in?
23. What’s the weirdest item you keep by your bed?
24. If you got to choose your name, what would it be and why?
25. Who was your first celebrity crush, and are you into them?
26. What’s your most unpopular food opinion?
27. What would be the tagline to the sitcom of your life?
28. If you had to eat the same meal at least once a day, what would it be?
29. If you were the ruler of the world, who would be your top adviser?
30. What’s the weirdest thing you wanted to be when you grew up?
31. If you could have a lifetime supply of anything, what would it be?
32. What item do you hope will be obsolete in 20 years?
33. What’s the strangest thing you’ve ever eaten?
34. What is your favorite room in your home?
35. If you could change anything about yourself, what would you change?
36. If you could get rid of one thing in the world, what would it be?
37. What was the funniest thing you’ve seen recently online?
38. What was the worst style choice you ever made?
39. What interesting skill do you want to learn?
40. If you could go to outer space for free, as a tourist, would you do it?
41. If you could effortlessly pick up a skill in an instant, what would it be?
42. If you could have an extra hour of free time every day, how would you use it?
43. What invention would you most like to see in your lifetime?
44. If you could choose to remain an age forever, what age would you choose?
45. What has taken you the longest to get good or decent at?
46. What was the most embarrassing thing you have done on a date?
47. What was the most difficult thing about your childhood?
48. If you could have any animal as a pet which one would it be and why?
49. What’s the best or worst prank you’ve played on someone?
50. If you could have any celebrity be your best friend, which celebrity would you pick?
Dumb and Funny Questions to Ask a Guy
In this section we have got you some of the dumb questions to ask a guy. You can ask these quite dumb and cute questions to make yourself look naïve.
1. Intense pain for ten minutes or dull pain for one day?
2. What has been on your ‘to-do’ list the longest?
3. What’s the best knock-knock joke you know?
4. If you could do anything in the world as your career, what would you do?
5. Which celebrity would you pick to exchange lives with?
6. If you could get rid of any current trend, what would it be and why?
7. What’s the craziest thing you have ever done?
8. If you could be invisible for a day, what would you do?
9. Who would win in an arm wrestle, you or the person next to you?
10. If you were a sitcom character, what would be your catchphrase?
11. What’s your hot take on a very popular movie or TV show?
12. What non-dairy item do you think would make a great alternative milk?
13. In your opinion, what’s the funniest word in the English language?
14. What’s a pizza topping that most people hate but you secretly love?
15. What’s the weirdest movie you’ve ever seen?
16. What’s the funniest song you know all the lyrics to?
17. If you were on AIM in the early aughts, what was your screen name?
18. Do you hang your toilet paper over or under?
19. What’s a funny habit you do at home while no one is watching?
20. Who’s a fictional character you would hate to be sat next to on a long flight?
21. What’s a niche joke you know that probably only you find funny?
22. What’s an awkward text you once sent to the wrong person?
23. Would you rather pee every time you laugh or shart every time you sneeze?
24. What’s the most awkward interaction you’ve ever had with another person?
25. What’s the most gimmicky home gadget you own?
26. What funny question would you ask me to make me laugh?
27. If your dog could talk, what would they say?
28. What’s the most ridiculous thing you would buy if you were given a million dollars?
29. What’s your funniest high school memory?
30. If you were sent back in time to 1,000 years ago, how would you prove that you’re from the future?
31. What funny saying would be written on your tombstone to describe the life you lived?
32. What’s something that’s not illegal that feels illegal?
33. What’s a conspiracy theory you kind of believe to be true?
34. What was the most horrible-tasting dish you ever made?
35. If you had something written on your face, what would it be?
36. What was the most embarrassing thing you did in public transport?
37. Can you share your biggest DIY fail story?
38. What is one completely useless thing that you can spend hours doing?
39. Have you ever waved at someone to realize later that they are the wrong person?
40. What was the best excuse you ever made for not attending a class at school that solved the situation?
41. Can you share the lamest funniest joke you ever heard?
42. What was the craziest thing you have ever written in your answer sheet?
43. Suppose you meet your ex after a really long time, what would be your first reaction?
44. What was the most ridiculous lie someone said on your face?
45. If you could charge a million dollars for a service provided by you, what would that be?
46. What was the smartest lie you ever told?
47. Suppose you are the monarch of a country, what would be the national emblem?
48. Which tv-show plot do you find horribly illogical?
49. How would you react if you find out that your best friend has a secret crush on you?
50. Have you ever eaten a cookie that fell on the floor?
Silly and Funny Questions to Ask a Guy
In this category we have arranged for you some of the silly questions to ask a guy. Here are few silly and funny questions to make your conversation intriguing and prolonged.
1. What is the one thing that movies never get right?
2. Zombies or super heros – which seem more exciting to be real?
3. What do you think is better – funny or sexy?
4. Did you ever try something too confidently but failed miserably?
5. What one thing you used to do thinking it looks sexy but later found out the opposite?
6. How many times do you wear a t-shirt before washing it?
7. When was the last time you skipped a shower?
8. Can you offend someone without doing anything offensive?
9. What do you think is the quickest way to hurt someone’s ego?
10. If you could change one thing about any of your favorite sports to make it funny, what would you do?
11. What was the weirdest hobby you ever heard about?
12. If you could change one thing about human anatomy, what would be that?
13. What was the dumbest way in which you hurt yourself ever?
14. If you had to, what crazy name would you choose for your kid to make them embarrassed for life?
15. Can you share a secret talent of yours that can make others feel jealous of you?
16. Who is the dumbest celebrity according to you?
17. Can you recommend a good smart speaker?
18. How much wood would a woodchuck could chuck if a woodchuck could chuck wood?
19. Did you ever want to curse and hug me at the same time?
20. What was the first thought that came to your mind on our first encounter?
21.Did you ever create a rumor, intentionally or unintentionally?
22. Who is the one person whom you would never want me to hang out with?
23. Would you prefer to be the pretty villain or ugly princess?
24. Did you ever overhear someone bitching about you on your back?
25. Do you have a crush on an anime character?
26. If you have to boast about having a sexy boyfriend, how would you do it?
27. Can you make the ugliest face saying the sexiest pickup line you can think about?
28. Did you ever get happy finding that I too hate the person you hate secretly?
29. When was the last time you wanted to punch someone?
30. Did someone ever treat you with food that you had a hard time finishing?
31. If you could detach one of your body parts, which one would it be?
32. Who is one person who is most likely to be a serial killer?
33. Can you make yourself seem like a psychopath by just one text?
34. What is the weirdest excuse someone gave you for not texting back in time?
35. When was the last time someone left you on reading?
36. If you could swap one thing in real life from social media, what would it be?
37. What is the strangest place you had to spend your night?
38. If you had to, what kind of secret society would you begin?
39. What gift would you pick for your enemy?
40. What flavor would be the funniest to add for an ice cream?
41. Can you share your useless super powers?
42. What is the creepiest message you ever got?
43. Did you ever play dumb to avoid work?
44. What one invisible thing you wished was visible?
45. If you had to start a rumor, what would it be?
46. If you had to choose one – would you always speak truth or always lie?
47. Which is more tiresome – brushing your teeth or taking a bath?
48. Who do you think would win if a dog and a cat could have a debate?
49. If you had to eat either grass or grasshopper, which one would you choose?
50. Which inanimate object do you think would be dumbest if it had life?
Juicy and Funny Questions to Ask a Guy
In this category we have arranged for you some of the juicy questions to ask a guy. You can ask these juicy and hilarious questions to make your conversation captivating.
1. If you were a brand, what would be your brand tagline?
2. Horn or tail – what would you choose if you had to?
3. How would you react if you see a huge fly on the wall beside you when you lazily open your eyes from sleep?
4. How is SpongeBob SquarePants while its parents are round?
5. Can a bedroom be a bedroom without a bed?
6. Why do vampires suck blood when they can just have some Vitamin D supplements?
7. If running cars too fast is illegal, why are cars made to run that fast?
8. Why is it called life insurance when it is given after one’s life ends?
9. How would mermaids choose a foundation for themselves since they have two kinds of skin?
10. If you could get a remote control of anything in the world, what would it be for?
11. Why is lipstick called lipstick when it doesn’t stick your lips together?
12. If you could replace easter eggs with something else, what would be?
13. What is the most embarrassing moment you have experienced being you?
14. If anything could fall from the sky instead of rain drops, what would you choose?
15. What is the one weird unwritten rule at your home?
16. What is the craziest hairstyle you have ever seen?
17. What is the weirdest thing you spotted at someone’s house?
18. What is something that has a funny smell yet you sniff it nevertheless?
19. If you take a challenge of losing a game but you win, then are you a winner or a loser?
20. What is the most annoying noise you can make?
21. What is the worst song you are addicted to?
22. If you fall in love with a vampire, would you volunteer to give a little blood to them regularly?
23. How often did you get annoyed today?
24. What is the one thing that you can share with a stranger but not with your parents?
25. Where do you not see yourself in ten years?
26. What is the most horrific story you ever made as a child?
27. Do you know someone who is completely harmless but gives a dangerous vibe?
28. What one thing do you do that you pretend to hate in front of others?
29. If you had to replace your nose with anything, what would it be?
30. If you could be an elf for 24 hours or turn into a bird, what would you choose?
31. Did you ever try touching your nose with your tongue?
32. What was the most horrific children’s book you ever read?
33. How would you feel if your friend passed the test copying your paper but you failed?
34. What is the one thing you want to invent or create if you could?
35. If your Google assistant could tell others your biggest secret, what would it be?
36. How would you describe an alien, why do humans show aliens as some kind of villain in movies?
37. Is there something that your friends would warn me about you if we start dating?
38. Can you share the plot of any one of your favorite movies in one sentence?
39. What is your favorite 80’s style that is weird yet cool?
40. Do you know someone who acts coy but is dirty?
41. What is the coolest phone ringtone you have ever heard?
42. Do you think it would be sexy if humans would sniff each other as a form of greetings?
43. What one thing that superheroes wear you find wild?
44. What is the weirdest hair colour have you ever seen?
45. What would happen if our nails are replaced by our teeth and vice versa?
46. What inanimate object would you choose to be if you have to be one for a year?
47. Smell like butter or have green colored sweat – what would you choose?
48. Don’t you think marriage is a kind of business?
49. Why do we associate the heart to emotions though all it does is pumping blood?
50. What do you think is the logic behind having buttons on different sides of shirts for men and women?
Funny Questions to Ask a Guy to Get to Know Him
In this category we have arranged for you some of the fun questions to ask a guy. Here are some funny and cute questions you can ask your guy in order to get to know more of him.
1. If you ran into God randomly, what would you do?
2. What one thing about our world do you think an alien would find totally weird?
3. What is the wildest thing you wrote as a child?
4. Did Noah have woodpeckers on the ark?
5. So, why do you think farting is embarrassing when it is a natural bodily function?
6. What is the most annoying sound one can hear in the morning?
7. Do you think you can survive without your smartphone for the rest of your life?
8. Can someone get sexually attracted to themselves if their clone from the parallel world appears?
9. Food that looks like dirt or tastes like dirt – what would you have if you had to?
10. If you’re a villain, which ‘superhero’ character would you choose against you?
11. Why do you think we assume that a life partner needs to be someone romantically involved with us?
12. Do you think a perfectly healthy relationship is boring because it is just too perfect?
13. Why is fast food called fast when actually it helps us not fasting?
14. If you were a place, when would be your tourist season?
15. What is the most freaking mistake I made as a child?
16. If you could rate all of us from crazy to normal, how would you do it?
17. Do you remember any incident when we fought like crazy?
18. Are you having any secret love affair now?
19. What did I ever tell a child that freaked you all?
20. Did you ever tell a funny lie to all of us that you want to confess now?
21. What one thing I used to do as a teen that made you all troubled?
22. Among all of our family members, who is most likely to be a hopeless lover?
23. Can you tell the most embarrassing name you got at your school?
24. What was the wildest thing for which you have ever spent all your pocket money?
25. If someday your doppelganger appears, how would you prove that you are the real one?
26. Which seemingly cute looking creature do you find creepy?
27. Have you ever cursed someone knowing they couldn’t understand or hear what you are saying?
28. Did you ever fart and blame it on someone else?
29. If your happiness makes your enemy happy, are they still your enemy?
30. What is the biggest cultural shock you ever faced?
31. Who makes disgusting food but you never told them out of politeness?
32. What are the things you think about while in the toilet?
33. Can you tell what was the last lie you told?
34. What would you do if you and your friend had a crush on the same person?
35. Can you do a bell dance now as your life depends upon it?
36. Have you ever burped in the middle of a kiss?
37. Did you ever farted in public and then pretended that you have not done it?
38. Do you give imaginary Oscar-winning speeches or something in the shower?
39. What’s your most favorite animal in the world?
40. What’s the first thing you do when you are bored?
41. Which Pokémon starter would you choose: Bulbasaur, Squirtle, or Charmander?
42. If you were a serial killer, what would your modus operandi be?
43. If there were no consequences for a day, what would you do?
44. If I were to summon you via black magic, which 5 items would I need in each corner of the pentagram?
45. How many zombies have you killed in your life?
46. If you were on death row, what would your last meal be?
47. As of right now, if you were to die, what would you leave me in your last will and testament?
48. What songs are on your zombie killing soundtrack?
49. Would you rather own a dragon or be a dragon?
50. If you could eat only one food for the rest of your life, what would it be?
Funny Questions to Ask a Guy Over Text
In this category we have arranged for you some of the funny questions to ask a guy over text. Here are some really funny and quirky questions you can ask your guy over texts to elongate your conversation.
1. What do you think is the worst way to die?
2. If you could only eat one dish for the rest of your life, what would it be?
3. What would you pick if you could choose your own superpower?
4. If you could pick one member in the group to take to a deserted island, who would it be and why?
5. If you could pick one member in the group to kill, who would it be and why?
6. If you could be an animal for a day, which would you choose?
7. If you were a drag performer, what would your drag name be?
8. What would you do first if you were invisible for a day?
9. If you could pick between dating a superhero or a supervillain, who would you choose?
10. Would you rather eat only pickles for a week or drink only soy sauce for a week?
11. Would you rather never use emojis again or never spell right again?
12. What was the most embarrassing thing that happened to you in middle school?
13. What was the most ridiculous thing you got in trouble for in school?
14. What’s your most awkward school dating story?
15. What was the best thing that happened to you in school?
16. What’s your most exciting college party story?
17. If you could write a tell-all book about your workplace, what would you call it?
18. Who do you think has the best fashion sense in the workplace?
19. Name one thing that you’ve always imagined doing but never did?
20. If you had to break the ice during some awkward silences, which joke would you crack?
21. All things considered, the worst advice you’ve followed and regretted?
22. If trapped in a horror movie, who would be the first one to die from your team?
23. If you could jump inside any book, fiction or nonfiction, where would you go?
24. Have you ever mistakenly texted someone you were not supposed to?
25. If you never had to sleep, what would you do with all those extra hours each day?
26. If you could devise a new invention, what would you create?
27. sing like a rock star or cook like a gourmet chef?
28. What’s the grossest food you ever had to eat to be polite?
29. What show are you most likely to binge-watch?
30. If you could switch one thing about yourself, what would it be?
31. Which cartoon character would you like to be?
32. If you had a TV show, what would the name be and who would play you?
33. What crazy activities do you dream of trying someday?
34. If you could eliminate one food so no one could eat it ever again, what would you destroy?
35. What famous animal movie character do you like the most?
Funny Questions to Ask a Guy in Person
In this category we have arranged for you some of the hilarious questions to ask a guy. Here are some finest and hilarious questions you can ask your guy to let the conversation going.
1. If you could make a place disappear, which one would it be?
2. Can you live without your smartphone for 24 hours?
3. What is the best compliment you’ve received?
4. What do you want to try for the first time in the year ahead?
5. What was the first significant thing you bought with your own money?
6. In what ways do you consider yourself fortunate?
7. Would you rather live in the ocean or in deep outer space?
8. If you had a time machine and could go back in time, what would you change in history?
9. If you were a pet, what would you want to do to your owner?
10. If you could be any food, what would you be and why?
11. What is something you did when you were younger that makes you cringe to think about?
12. What is the most adventurous thing that you’ve done?
13. When have you done something outlandish for what you usually do?
14. What’s the one thing in your daily routine that you wish you could eliminate?
15. Would you rather be the person giving or taking advice?
16. What’s the worst thing someone has ever done to you that you found incredibly difficult to forgive?
17. If you could be on any game show, which would you choose?
18. Would you rather go back in time or be transported to the future?
19. Would you go with aliens if they arrive on Earth?
20. If you were famous, what would you be famous for?
21. If you were to be reincarnated as an animal, what would it be and why?
22. If you were to choose a fictional family to be with, who would they be and why?
5 Tips for Picking Funny Questions to Ask a Guy
The funny questions to ask a guy to begin a discussion with him might influence how the encounter ends. If the guy you are going to speak to does not know you that means these amusing fun questions to ask a guy will convey your personality and aim to that individual.
The finest icebreaker is laughter. It helps to stimulate the fire between you two if you can start a conversation with the mentioned list of funny questions to ask a guy and make him chuckle.
- Whenever you feel like you are stuck in the conversation and don’t know how to ask the important details about that person, go toward the lighter side and make your conversation comfortable and light hearted for that person by asking funny questions to ask a guy.
- If you think this guy seems the best match for you and you have done this estimation beforehand so do not waste and do not let him slip away. Amuse him through your quirky and funny personality by asking some witty fun questions to ask a guy.
- Do not ask so much crazy and juicy questions, rather ask some dumb and stupid fun questions to ask a guy as well, you don’t have to look like a perfectionist since nobody can be.
- You can deviate any uncomfortable situation by asking some really funny questions to ask a guy. Break the ice of formalities and culture and delve yourself and him into more comfortable and contemporary style of communication.
- Do not just ask fun questions to ask a guy, ask few decent and sane questions as well to make your conversation versatile and powerful. It is always a better option to distract someone from a boring conversation by asking fun questions but not all time. Prove yourself that you are serious for him.
Final Thoughts on Funny Questions to Ask a Guy
These funny questions to ask a guy can only assist you in getting started; the rest is up to you.
Do not rush. Allow adequate time for him, as well. A good connection takes time to develop. Maintain your patience.
Be sincere and trustworthy. Beginning with a falsehood can weaken the foundation of your connection. This may lead to eventual trust concerns. It is preferable to begin with the truth.
Make an effort to be courteous to him. These funny questions to ask a guy should not annoy him.
Another key aspect of a great date is participation. If you keep asking fun questions to ask a guy without giving your partner a chance to respond, the conversation will become uninteresting and strange for him.
Allow him plenty of room at first. Guys adore their own space. Encourage him to share his interests and dislikes.
Allow him to speak and ask you questions, and then respond with confidence and honesty.
The dialogue is always two-sided. To be effective, you must both talk and listen. Make an effort to pay attention to him and make him feel valuable.
Remember to appreciate yourself. To receive it from your lover, you must first love and respect yourself.
Be genuine. Don’t be too concerned. Simply laugh and flirt with him during your time together. Entertain your date with the above-mentioned list of funny questions to ask a guy.
