One does always think of some random questions to ask a guy on their first meetup, but the wrong random questions can ruin the whole conversation. Let’s discuss this in detail.
Conversation starters aren’t always easy, especially when you are about to talk to a guy. Of course, you don’t want your first conversation topic with a guy to be about the weather! We think that should be the last thing to discuss with a guy if you don’t want to sound boring.
Thus, think of some good random questions that keep you guys engaged whenever you are in doubt.
But if you are struggling really hard to come up with a few random questions to ask a guy, then finally you have reached the right place to open the door of conversation with the other person through these random funny questions to ask a guy written below.
Have a look at these random questions to ask a guy and enjoy!
Table of Contents
Best Random Questions to Ask a Guy
If you are looking for the best random questions to ask a guy, there could be no better place than this where you have many questions to choose from. Check out the given list and select the best questions out of all.
1. What’s something that can’t be found or bought on the internet?
2. If you could fit your whole life into one picture what would it look like?
3. What’s the weirdest thing that has happened to you in a car?
4. What’s your favorite sounding word?
5. Who around you has the worst luck?
6. What’s the perfect temperature to set the thermostat at?
7. What company or franchise do you wish would go out of business?
8. Which musical artist is greatly overrated?
9. What’s the funniest or most amazing cell phone cover you have seen?
10. Who in the movie business seems the most down to earth?
11. What behaviors make you think a person is creepy?
12. What’s the fullest you’ve ever been?
13. If you could rename the street you lived on, what would you rename it?
14. What animal best represents your personality?
15. What’s your “going to bed” routine?
16. What do your clothes say about you?
17. What piece of technology brings you the most joy?
18. What are some songs you know by heart?
19. Could you survive in the wilderness for a month?
20. What was the last thing that you fixed?
21. Is there an app that you hate but use anyways?
22. What book do you wish would be turned into a movie?
23. Who is a better cook your mother or grandmother?
24. What was the last thing you created?
25. If you had to replace your hands with objects already in your house, what would you replace your hands with?
26. What song would you pay money to never hear again?
27. What three activities would you rate 10/10 would do again?
28. What looks delicious but tastes terrible?
29. What conspiracy theory do you actually believe?
30. What would be put inside a mental health first aid kit?
31. What first world problem do you have?
32. If you had to break one world record in order to receive one million dollars, what world record would you try to break?
33. What is the most fun thing someone could have in their backyard?
34. If the police raided your house right now, what is the most incriminating thing they would find?
35. What is the most interesting game concept you can come up with?
36. If there were internet Olympics, what sports would be in it?
37. What’s the most nightmarish creature you can imagine?
38. What is the most pleasant sounding name for either a boy or a girl?
38. What would be the funniest thing to fill a piñata with?
39. What are you really happy about being terrible at?
40. What game do you wish you could act out in real life?
41. What in a trailer automatically makes you assume a movie will be horrible?
42. What did you think you were good at but are actually quite bad at?
43. What is the most interesting thing you could do with 400 pounds of cheddar cheese?
44. What villain do you really feel for?
45. If you were challenged to a duel, what weapons would you choose?
46. If you put out a magazine, what would you name it and what would be in it?
47. What should the first colony on another planet be called?
48. What’s your most interesting character as a guy?
49. Would you rather go on a date with your best friend or turn your love interest into your best friend?
50. What do you think about the culture of men these days?
You might also like: Dirty Questions to Ask a Guy
Good Random Questions to Ask a Guy
When in doubt, think of some good random questions to ask a guy. But if you are having a hard time coming up with it, then do take a look at these questions below. A little randomness can go a long way!
1. If you could live on another planet, which planet would you choose?
2. What’s the craziest thing you’ve done with a crush?
3. Go into your search history, what’s the last thing you looked up on Google?
4. What’s the last thing you watched on YouTube?
5. What was the last playlist you created?
6. What do you think about new music releases right now?
7. Why is the divorce rate in the United States so high?
8. If you represented Earth while meeting aliens for the first time, what would you say?
9. Assume you had to describe the meaning of love in one word, what word would it be?
10. Presume you had to describe life in one word, what would you use and why?
11. If you could be any fictional character in a book or movie, who would it be and why?
12. Who do you know that has the worst luck?
13. What’s your dream job that pays very little money?
14. How do you know exactly what to say when in trouble?
15. What type of animals do you think we were in our past lives?
16. What’s one of the funny stories that you have from high school?
17. Who do you have the most interesting conversations with?
18. What’s the most amazing cell phone cover you ever owned?
19. If you had to play one game in Las Vegas right now, what game would it be?
20. What’s your biggest pet peeve about women in today’s culture?
21. What’s your favorite thing to bet on?
22. Are you going to be watching any sports drafts this weekend?
23. What would you rather be watching, hockey or football?
24. If you had one friend go to prison, who do you think it would be?
25. Where do you see your friend’s lives going in the next 5-years?
26. What is your favorite healthy food snack to have at night?
27. What’s your favorite unhealthy food snack?
28. When you’re checking out at the grocery store, what snack do you normally get?
29. When you’re in a line at the grocery store, what magazine do you normally buy?
30. If you were to go to a book store, what type of books would you be getting?
31. What movie or TV show are you going to watch tonight?
32. Do you play any sports with your friends on the weekends?
33. If you could choose to do anything this month, what would it be?
34. What are your plans for this weekend?
35. Which celebrity would make the worst leader of a country?
36. What is the most interesting piece of trivia you know?
37. If you designed and built a tree house, what would it look like and what would be in it?
38. What movie can you watch over and over and never get tired of?
39. What would be the consequences of a scientific discovery that extended the life span of humans to 500 years?
40. What high level job do you think you could lie your way into with no experience and no one would notice?
41. What long shot have you taken that really paid off?
42. What would you not do for 5 million dollars?
43. What is something that most people get wrong?
44. What’s the worst and best thing about being male?
45. What is the most useless thing you know how to do?
46. Who or what is your nemesis?
47. How many phones have you broken or lost?
48. What movie do you wish life was more like?
49. Who has completely lost your respect?
50. What’s the biggest doubt you have?
51. What childish thing do you still enjoy?
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Fun Random Questions to Ask a Guy
Conversation starters can be tough for those who don’t interact with people often. However, if you have a good sense of humor then go forth with fun random questions to ask a guy, and don’t forget to add some puns to spark up the conversation.
1. What was your best drop the mic moment?
2. Who would win in a deathmatch, God or the Devil?
3. What’s the most embarrassing thing that your mom ever caught you doing?
4. What’s one thing that you need to put in your bathroom drawer?
5. Who is a person that you’d like to marry right now?
6. Why did the idea of “beta males” become a thing in our society?
7. How long do you spend getting ready in the morning?
8. Did you ever ditch a date?
9. Have you ever had to use the bathroom for a long time on a first date?
10. What’s something funny that you’ve done with your friends?
11. What’s a funny story that you have about your life right now?
12. Who is one person in this world that you would marry, k#ll, and k#ss?
13. Would you rather lead the relationship or had someone else lead the relationship?
14. Do you think that more apes will turn into humans in the future?
15. If you could be any food, what food would it be and why?
16. What’s something classy if you’re rich but trashy if you’re poor?
17. What do you think we’d be doing right now if the internet was never invented?
18. What’s your favorite curse word?
19. What’s the riskiest style choice you’ve made in the past?
20. Do you ever find yourself yelling at your GPS?
21. What kind of pranks have you pulled?
22. If we went on a crime spree together, what crimes would we commit?
23. What movie do you think is better than the book it’s based on?
24. Would you be willing to babysit your younger self?
25. What’s your least favorite cliché job interview question?
26. Have you ever had 15 minutes of fame?
27. What’s the worst thing you’ve done on a dare?
28. Do you sing in the shower?
29. If you could choose a superpower, what power would you want?
30. Which direction do you hang toilet paper?
31. If you could be transported into any film franchise which one would you choose?
32. What is your best corny joke?
33. Have you ever been asked to leave a public place?
34. What’s the cheesiest line you’ve ever used that actually worked on a girl?
35. What is your favorite part about being an adult?
36. Would you rather be hot or cold?
37. What fictional character do you relate to the most?
38. What is the one movie you’ve seen more times than you can count?
39. Have you ever been to a palm reader?
40. What is the weirdest thing you’ve ever bought?
41. What is the most embarrassing thing that ever happened to you?
42. What is your pop culture guilty pleasure?
43. What word do you hate?
44. What celebrities have you met?
45. If you could listen to only one song for the rest of your life, what song would you choose?
46. When was the time you laughed the hardest?
47. What is the weirdest reason you ever broke up with someone?
48. Wanna see how much alcohol it takes to die?
49. Do you think cockroaches have souls?
50. Did you know that eating pizza every day is healthier than dying?
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It doesn’t have to be that serious to get to know the other person. These cute questions to ask a guy can elicit information about his childhood adventures, greatest experiences, and individual interests.
1. What’s the single most important thing you have done in your life?
2. What’s one minor regret you have?
3. If you had a disease named after you, what would be the symptoms?
4. What’s your most common first thought when you wake up?
5. Do you think your childhood was better or worse than other people growing up in a similar place and time?
6. What’s the most absurd thing that has become part of reality?
7. What’s the dumbest rule you’ve been forced to follow?
8. What’s one thing you learned this week?
9. What’s a piece of advice that you wish everyone would take to heart?
10. What would be the absolute best pet to have?
11. Who would you want to play you in a movie about your life?
12. What was something you loved, but it never really took off or was ended before it’s time?
13. What genetic modification would you most like to have?
14. What happens more often than you’d like?
15. What’s your best podcast recommendation?
16. What fictional character did you / do you have the hots for?
17. What’s the biggest “scene” you’ve seen someone make in public?
18. What do you imagine the lives of super-rich people are like?
19. What would you recommend to someone if they had the day off and didn’t know what to do?
20. If States could date, who would be into who and why?
21. Would you travel to a foreign country all by yourself?
22. What would the exact opposite of you be like?
23. If there were an Olympics for average people, what would some of the events be?
24. What looks like it should taste better than it does?
25. Besides religion and politics, what topic always gets heated in your circle of friends and acquaintances?
26. On a scale of existential crisis to living the dream, how’s life going?
27. What would be the worst animal to be eaten by?
28. What’s the weirdest thing you’ve seen while driving?
29. What quote has always stuck with you?
30. What useless bits of information have you memorized and will probably never forget?
31. What’s an example of a modern masterpiece?
32. If you had to be stuck at one age forever, what age would you choose?
33. What common piece of advice or words of wisdom don’t actually make much sense?
34. What social media post has really stuck with you?
35. What’s something you boycott but don’t make a big deal of boycotting?
36. What are some small pleasures that make you way happier than they should?
37. When was the last time you felt completely out of the loop?
38. If you could run away from it all and start fresh somewhere new, would you?
39. What news headline would you most like to see?
40. What’s your definition of a good human being?
41. What are some of your favorite movies from each genre?
42. What language do you like the sound of, even though you don’t know how to speak it?
43. What’s the strangest hobby you’ve heard of?
44. What’s the best part of your day?
45. Who is the funniest actor or actress still doing movies, TV shows, or YouTube?
46. What activity or hobby is so filled with hateful people that it puts you off trying it?
47. What’s the worst slip of the tongue you have heard about or that has happened to you?
48. What have you really wanted to do for a long time but haven’t done yet?
49. What’s worse than you thought it would be?
50. If you could add one rule that everyone must follow when they use the internet, what would your rule be?
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Funny Random Questions to Ask a Guy
Making someone laugh is an absolute art. If you got the right random funny questions to ask a guy and made him giggle then believe us, you have just hit right on the mark! Have a look at these funny questions below and be certain that you don’t overdo them.
1. What is your go-to karaoke song?
2. What’s worse — bed head or hat hair?
3. Would you rather be too hot or too cold?
4. What is the worst superpower?
5. What is the weirdest dream you have had?
6. What ridiculous law would you create?
7. How do you think fruits got their names?
8. If you couldn’t shower with water, what would you replace water with?
9. What is the one thing that you would say to end any conversation?
10. If you could wake up in the body of any animal, what animal would it be?
11. What two body parts would you want to switch?
12. If you could make up a word, what would that word be, and what would it mean?
13. What word do you think is the funniest or sounds made up?
14. What is the grossest food combination you can think of?
15. What do you think the funniest movie is?
16. What meal would you not want your last meal on Earth to be?
17. What is your most embarrassing moment?
18. If you had to pick one, would you want to best friends with the Easter Bunny or Santa Claus?
19. What is the funniest joke you have heard?
20. What is the most useless object in the world?
21. What is the worst thing you have ever smelled?
22. What is the funniest joke you can think of right now?
23. What was the worst job you ever had?
24. If you could read people’s minds, what do you think they would say about you?
25. What song could be the theme song for your life?
26. If you became President, what would be the first thing you would do?
27. What is the funniest memory you have?
28. When you replace the toilet paper roll, do you set the flap over or under?
29. What is something that bothers you that probably shouldn’t?
30. What is one movie that you love that you are embarrassed about?
31. How do you deal with people that you don’t like?
32. What is the most pointless superpower?
33. What is your favorite dance move?
34. Do you believe in any conspiracy theories?
35. Who is famous that shouldn’t be?
36. What is the best prank you have ever pulled on someone?
37. What is the best pick-up line you’ve ever heard?
38. What song can you not help but sing along to when it comes on?
39. What is the weirdest thing you’ve ever said to a stranger?
40. If you could eat or drink one thing without ever gaining weight from it, what would it be?
41. Did you ever want to learn to ride a motorcycle?
42. If your parents didn’t like who you were dating, would you end it?
43. Do you think that most men marry their mothers?
44. Would you give up the love of your life for all the money in the world?
45. What, if anything, in your life do you consider to be expendable?
46. Would you rather be a sinner or a saint?
47. Which historical figure do you admire the most?
48. What is one extreme sport or activity you wouldn’t mind trying?
49. Do you believe in love at first sight?
50. What is one talent you’ve kept hidden from most people?
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Interesting Random Questions to Ask a Guy
You never know, when you could bump into a cute guy. So, it’s better to keep some questions handy. Get your hands on these random interesting questions to ask a guy and be ready for an engaging discussion.
1. What makes you smile no matter what?
2. If you were a superhero, what kind of secret identity would you have?
3. What was one time you really stepped out of your comfort zone?
4. Have you ever dated someone your family hated?
5. How many people have you seriously dated?
6. How can a woman gain your trust?
7. What’s the worst injury you’ve ever had?
8. Would you ever date a boss?
9. Have you ever dated a coworker?
10. What’s the worst job you’ve ever had?
11. What does your perfect day look like?
12. What’s the scariest dream you’ve ever had?
13. Who do you wish you could trade lives with?
14. What’s your least favorite thing about technology?
15. Did you get in trouble a lot in school?
16. What is your dream wedding like?
17. Where did you learn your favorite hobby?
18. What New Year’s resolution do you always make?
19. Are you a spender or a saver?
20. Would you rather go to work early and get out early, or go to work late and get out late?
21. What did you think was silly until you tried it?
22. If you had to choose, would you rather be a model or an actor?
23. Do you have a favorite Kardashian/Jenner?
24. What’s your favorite reality show?
25. What is one tradition you love the most?
26. What’s your favorite family memory?
27. How would you describe me to someone who doesn’t know me?
28. Has anyone ever walked in on you naked?
29. What is something you took for granted in your last relationship?
30. When you have a problem or an issue, who is the first person you turn to?
31. Is it helpful to our culture and society to define religion?
32. Who was the last person with whom you had a relationship, and why did it not work out?
33. What is one item on your bucket list that you must complete before you die?
34. What are your own life aims?
35. Do you consider yourself to be a confident or secure individual?
36. What aspect of your self-image would you change if you had to?
37. What would you say if a fortune teller had to tell you the solutions to the universe’s questions?
38. What would you ask God if you could ask him anything about life?
39. Who do you imagine you’re talking to when you consider who god is?
40. Do you pray to god on a regular basis?
41. Do you believe that only fans is beneficial to our society and culture?
42. What do you think the future holds for our culture?
43. What do you think the social implications of p##nography are?
44. Isn’t it strange that Adam and Eve were brother and sister?
45. How much does it take to make you a little tipsy?
46. Would you have another drink in an ideal world?
47. What would you think if we changed our location to something more intimate?
48. Do you believe this lighting is suitable for us?
49. Is it just a chance that your shirt looks so beautiful on you, or did you get it custom-fitted?
50. When it comes to the female body, what type of look do you prefer?
Random Questions to Ask a Guy Over Text
We’ve all experienced those bothersome, impersonal, and simply empty messages from someone we’ve recently talked to. Texts like these are actually a sign of nervousness to initiate a conversation. Thus, for your ease, we’ve jotted down random questions to ask a guy over text.
1. What area of your body do you consider to be your favorite?
2. Do you want to join me on an adventure?
3. Would you like to see my home, just in case?
4. Do you want to exchange one Italian kiss, or a few?
5. Will you be enticed to sink your teeth into my dessert?
6. Is everything fair in love and war?
7. Would you like to dig a little deeper into my meal with me?
8. Do you want to risk the burning depths of hell with me by purchasing that chocolate cake?
9. Do you know who has the worst luck in the world?
10. What is your ideal part-time job that pays very little?
11. When you’re in danger, how do you know what to say?
12. What creatures do you believe we were in our previous lives?
13. Who are the people with whom you have the most interesting conversations?
14. What is the most wonderful phone case you’ve ever had?
15. What would you say to your President if you happened to run into him on the street?
16. If you had to choose one person to train with, who would it be?
17. If you win a lot of dollars in a lottery then what would you do with that money?
18. What can be a one solution for world problems?
19. What has been the most terrible incident that has ever happened to you?
20. Where do you see your life in the next 5 years?
21. What is your most favorite memory till now?
22. Could you marry someone outside your faith?
23. What is the real meaning of marriage for you?
24. What is the most memorable moment that you never want to forget?
25. What are the 3 most important things on your bucket list this year?
26. What do you think your family and friends would say about me if they met me for the first time?
27. How many kids do you see yourself having in future?
28. Do you ever think that you would become a baby daddy?
29. Would you dump your girlfriend for a date with your famous crush?
30. What do you think is the most handsome and hottest male celebrity?
31. Who is your female celebrity crush and from how much time?
33. What song would you like to dance to at your own wedding?
34. Do you prefer to watch television alone or with a partner?
35. Do you prefer to exercise at a gym or at home?
36. Do you prefer bars or clubs for having fun?
37. Do you like to watch Netflix?
38. What is your most favorite way to relax after a tiring day?
39. Are you a vegetarian or a non-vegetarian?
40. What is your bad habit while traveling? Do you want to improve it or just ok with it?
41. Which country would you like to choose between India and China?
42. What’s the funniest date thing you’ve ever done?
43. What is one thing you aren’t proud of from a previous relationship?
44. How would you spend all of the money in the world if you had it?
45. What is it about your crush that really turns you on?
46. Which would you prefer: a kiss on the neck or a kiss on the hand?
47. On weekends, what is your favorite game to play?
48. What’s the worst thing you’ve ever done with a female in a relationship?
49. What is the most bizarre thing you’ve ever done with a loved one?
50. What has been the worst date you’ve ever had?
Random Questions to Ask a Guy You Like
Whenever you get a chance to meet someone you like, you obviously make sure that you don’t ruin the moment with a useless conversation. For this reason, this article has covered a couple of random questions to ask a guy you like.
1. Do you think men and women should have separate roles in the home?
2. Who would you want to look like if you could appear like any celebrity, and why?
3. What is something that all guys should do for their girlfriends?
4. Do you enjoy talking on the phone or sending text messages all day?
5. Would you rather have a long walk and talk on a date or go out on the town?
6. What’s your favorite place for a drink?
7. Do you prefer to be active or passive?
8. What is the craziest thought that has ever entered your mind?
9. Have you ever broken out laughing while having s#x?
10. Which aspects of making love do you believe you could improve?
11. Which part of your body do you hate the most?
12. Is it legal to gaze at you as often as I do?
13. What do you think about us skipping dinner and going somewhere else?
14. Isn’t it about time you used those sexy forearms?
15. Which part of my body do you believe is the most gentle?
16. What is the most sensitive area of your body?
17. What is the most exciting film you’ve ever seen?
18. Would you like to join us on a cocktail binge to see where we end up?
19. Is it true that the taste of pleasure comes from a stranger’s lips?
20. After a hard night, how do you feel about a healthy breakfast?
21. Which place do you believe has the better interior design?
22. Would you like to arrive at work early and leave early, or arrive late and leave late?
23. Before you tried it, what did you think was silly?
24. Would you rather be a model or an actor if you had to choose?
25. Which reality show is your favorite?
26. What is one of your favorite traditions?
27. If you didn’t know me, how would you describe me to someone who didn’t know me?
28. What is a favorite family memory of yours?
29. Has anyone ever caught you naked in your house?
30. What did you take for granted in your previous relationship?
31. When you’re bored, what do you daydream about?
32. Where have you ever kissed someone in the weirdest place?
33. What is the strangest thing you’ve recently seen in the news?
34. Is there anything about you that you hope your mum never finds out about?
35. Would you prefer to spend a Saturday night out with your friends or with a woman?
36. What is your most appreciated feature?
37. Would you rather have the power to see through walls or the ability to read people’s minds?
38. Do you believe that everyone has a single soulmate or that everyone has several soulmates?
39. Do you know how to identify if someone is lying to you?
40. What is the strangest dream you’ve recently had?
Random Questions to Ask a Guy to Get to Know Him
Asking questions straight away to a guy can be a bit tough but in reality, it can break the ice between you two. Catch a glimpse of these random questions to ask a guy to get to know him more.
1. What is your favorite thing to do on a rainy day?
2. What was your favorite thing to do during recess?
3. What toy did you always want as a kid, but no one ever bought for you?
4. At an amusement park, what ride do you just have to go on?
5. If you could cook any dish perfectly, what would you choose?
6. What is your happiest childhood memory?
7. What did you and your friends do for fun in middle school?
8. What is the best present you’ve ever received?
9. What is your idea of a perfect Sunday afternoon?
10. When you were a kid, what career did you want to have?
11. What has been the best year of your life so far?
12. If you had to go back to school, what would you study?
13. What relationship cliché do you think is true?
14. What are your relationship deal breakers?
15. What is the best advice anyone ever gave you?
16. If you were going to start a charity, what would it be for?
17. What cause have you volunteered for that you feel passionately about?
18. How do you like to be treated when you’re sick?
19. Do you think it’s possible for men and women to just be friends?
20. If you could have any skill without having to work for it, what would it be?
21. If you could bring one person back to the dead for a day, who would it be and what would you do?
22. If you could change your name to anything, what would you pick?
23. If you could go back to any moment in your life and do things differently, would you?
24. If you could wake up tomorrow and be fluent in any language, what language would you choose?
25. If you could inhabit any movie, TV show, book, or other fictional universe, where would you live?
26. If you were going to get a tattoo today, what would it be of?
27. If you could trade places with one person for a day, who would it be?
28. If you could eat only three foods for the rest of your life, what three would you choose
29. Have you ever pranked anyone? Have you ever been pranked?
30. What fictional character do you have a crush on?
31. What is the hardest decision you’ve ever made?
32. What is the biggest risk you’ve ever taken?
33. What was the most difficult time in your life?
34. What bad habit do you have that you would you like to break?
35. What is one thing you wish you could change about yourself?
36. Have you ever gotten anyone pregnant?
37. What would you change about your childhood?
38. If you could only watch one movie for the rest of your life, what would it be
39. What’s the best thing about your life right now?
40. When you’re feeling super lazy, what’s your guilty-pleasure Netflix show?
41. What is one thing that brings a smile to your face, no matter the time of day?
42. Can you tell me one thing, big or small, that you’ve never told anyone else?
43. If you could only watch one movie for the rest of your life, what would it be?
44. What’s the hardest thing, physically, you’ve ever done?
45. If you had to lose one of your five senses, which would you give up and why?
46. What’s one thing you’re super passionate about?
47. If you could only eat one food for the rest of your life, what would it be?
48. When you’re feeling down, who or what is your biggest go-to person or activity?
49. What’s one thing about yourself, personality-wise, that you like?
50. What’s one thing about the opposite s#x that you’re attracted to?
Deep Random Questions to Ask a Guy
If you guys have been together for a long time now and your relationship is getting serious with time, then it’s critical for both of you to know about each other values and whether you guys are on the same page or not. So, without any further delay choose random deep questions to ask a guy from the given list.
1. If tomorrow was your last day on earth, what would you do in your last 24 hours?
2. If someone gave you a million dollars right now, what would you spend it on?
3. What’s one thing you want to do before you die?
4. If you could live anywhere in the world, where would you live?
5. What is the best compliment you’ve ever received?
6. What’s your favorite social media profile?
7. If you had the option to hit restart and begin life all over again, would you?
8. What’s one thing you wish you could change about yourself?
9. What’s your guilty pleasure snack, drink, or junk food?
10. What’s your favorite thing to do on the weekends?
11. Have you ever made a decision that changed your entire life?
12. What’s your favorite quote, line of poetry, or sentence?
13. Would you rather go out or stay in on a Saturday night?
14. Who is one person you could never live without?
15. What’s one thing you could never live without?
16. Have you ever done or accomplished something you never thought you could?
17. What do you imagine your future family will be like?
18. When was the last time you cried, and why did you?
19. What’s a random hobby you’ve always wanted to try but never have?
20. What’s one thing that totally relaxes you when you’re stressed?
21. Who in your family, immediate or extended, are you the most similar to?
22. What’s the scariest thing that ever happened to you as a kid?
23. What’s one thing you’ve learned about yourself from a past relationship?
24. What’s one thing that helps you decide you can trust someone?
25. What makes you blissfully, completely, smile-from-ear-to-ear happy?
26. What’s one thing, silly or serious, that you’re guilty of?
27. What’s one thing you want to achieve before you die?
28. Who is someone that’s impacted your life or helped you become who you are?
29. What’s one silly, little-kid item that you still have somewhere hidden in your room?
30. If you were writing a book about your life, what would the title be?
31. What is the first thing you notice about a woman?
32. Would you give away everything you had if you were promised to be forever young?
33. Where would you like to spend the rest of your life if you could?
34. If you had to describe the most intense moment of your life using only one word, how would you name it?
35. What would you tell your teenage self if you could send them some insights from the future?
36. What’s the best advice someone has ever given to you?
37. What do you love most about sleeping with a girl?
38. Where should I go if I want to spend my day as a tourist in this city?
39. Would you make breakfast in bed for a girl you fancy?
40. Have you ever walked away from someone you still loved?
41. Do you believe everyone we meet is meant to teach us a lesson about ourselves?
42. What are your feelings towards open relationships?
43. How would you handle someone hitting on your significant other?
44. Have you ever went and kissed a total stranger out of the blue just because you could not resist it?
45. Would you date someone who doesn’t have any books in their house?
46. What do you think about psychology and what role did it play in your life?
47. What are some of the things you wish a girl knew before dating you?
48. What is your opinion on men who refuse to use condoms?
49. How do you relate to people who suffer from mental disorders?
50. If I gave you a pen and paper what would you make out of them?
Flirty Random Questions to Ask a Guy
Planning a hot date with your significant other? Well, then get yourself hooked to this page because we have covered quite a variety of questions including random flirty questions to ask a guy. Enjoy!
1. Out of all of the places we’ve been intimate, where was your favorite?
2. Is there a fantasy that you have that you haven’t ever told me about?
3. Is there ever anything I do that you brag to your friends about?
4. Would you ever want to go skinny dipping together?
5. If we were building our dream home right now, what would it look like?
6. If you could design the perfect lingerie for me, what would it look like?
7. What is your favorite memory of our wedding day?
8. What is your favorite s#x scene you’ve ever seen in a movie?
9. What’s something you’d like to hear me say in the bedroom?
10. What do you think you’re best at in the bedroom?
11. What is the dirtiest, most NSFW text you have ever sent or received?
12. What’s your record for number of consecutive sessions in bed?
13. What do you think my secret fantasy is?
14. Do you think there is anything you wouldn’t want to do in bed?
15. If you had to tell the story of us with emojis only, what would it be?
16. What do you remember most about our first date?
17. If you could travel back in time to a different era, where would you go and why?
18. In a Genie in a Bottle situation, what would your 3 wishes be?
19. What’s the coolest thing you’ve ever gotten away with?
20. What is something that you thought would break you, but it only made you stronger?
21. Is there anything about our relationship that scares you?
22. If money, time, and obligation weren’t a barrier at all, where would you want to go right now?
23. What is the hardest thing you have ever done, physically or mentally?
24. What can you tell me about you that you’ve never told anyone else?
25. What does the ideal relationship look like to you?
26. What is your favorite song to get down and dirty to?
27. Where is your favorite place to be kissed on your body?
28. Have you ever been caught in the act?
29. Where is the craziest place you’ve gotten frisky?
30. If you could change one thing about yourself, what would it be?
31. Do you prefer adventure dates or chill dates?
32. What’s the most embarrassing thing that ever happened to you?
33. What is something surprising about you?
34. Would you rather kiss in the dark or kiss in the rain?
35. What’s the worst date you’ve ever been on?
36. What do you think are your most attractive qualities, physical and non-physical?
37. What’s your biggest turn on in a potential partner?
38. What physical feature do you find most attractive in a woman?
39. Are you enjoying meeting new people in a bar?
40. What goal have you accomplish in your life already?
41. What’s the most romantic thing you have done?
42. What was your favorite part of the day?
43. What song would you compare our relationship to?
44. What type of workouts do you enjoy?
45. What is your favorite way to relax after a long day at work?
46. Do you like to be in long term relationships?
47. Do you like light massages or deep muscle massages?
48. What was the most reckless thing that you have ever done?
49. Do you like a woman that is soft and sweet or more aggressive?
50. How do you feel when wear a suit and dress sharply?
If you want to level things up in your relationship, then these dirty random questions to ask a guy are perfect for you. Have a look at these questions and try asking them without making the situation awkward.
1. What is your most sensitive body part?
2. Could you guess my favorite part of your body?
3. Have you ever had a one-night stand?
4. Are you a spanker, hair puller, or both?
5. Which swim stroke describes your preference?
6. Have you ever been caught doing the deed?
7. Have you ever smelled your partner’s underwear?
8. Have you ever gotten hard when an older woman 3 times your age touched you?
9. Have you ever seen a disappointed look on your partner after s#x?
10. Have you ever confessed your love during s#x?
11. Have you ever wanted to kiss your teacher?
12. What is your ideal place to have s#x?
13. Have you ever licked off ice cream from your partner’s lips with your tongue?
14. What is the kinkiest thing you have done in the bedroom?
15. Have you ever made out in a club?
16. What mistake did you make in bed for a long time?
17. Have you ever fallen from bed while doing it?
18. Have you ever done it on your parent’s bed?
19. What is the difference between a one-night stand with a stranger and doing it while being in true love?
20. Would you have s#x with a person if you’ve only known them for a few days?
21. Do you like it if you are teased more before doing it?
22. If you could only lick one place on your partner for the whole life, where would it be?
23. Where do you press the most, during a session?
24. If you could choose one of your exes to do it for one night, who would you choose and why?
25. Do you like to push your partner against the wall while making out?
26. Have you ever imagined your parents doing it?
27. What would you want your girl to call you in the bedroom?
28. Do you prefer s#x on the phone or video call?
29. Who is the most unexpected person that hit on you?
30. Have you ever tried to imitate scenes from fifty shades of grey?
31. What is the weirdest way you have asked for a naked picture of someone?
32. Have you slept with anyone only to realize that you will never want to sleep with her again?
33. Have you ever taken off your partner’s underwear with your teeth?
34. Have you ever tricked your partner into licking you?
35. Do you ever want your partner to behave like a certain celebrity to seduce you?
36. Which movie character would you like to have a one-night stand with?
37. Have you ever been sexually attracted to any of your relatives?
38. Did you ever catch someone doing dirty while being on a trip?
39. Did you ever have a s#x chat with someone you barely knew online?
40. Don’t you wanna know the naughty little secrets your partner has never told you?
41. Have you ever sent a dirty text to your partner in front of family members?
42. Have you ever licked peanut butter from your partner’s body?
43. Would you love to do it in places besides your bedroom?
44. Would you have s#x with a woman 2 times your age?
45. Is laughing in the bedroom during s#x, inappropriate?
46. What is the most nonsexual thing in a woman that turns you on?
47. Would you love to lick off chocolate from your partner’s body?
48. Would you buy lingerie for your partner?
49. Do you like to smell your partner while having s#x?
50. Have you ever practiced kissing in a mirror?
Personal Random Questions to Ask a Guy
People usually resist themselves before getting personal with others on the first meet-up. Which is rightly so, but if you guys have already talked before, then it’s an ideal time to delve into each other personal life. Hence, we have brought you the perfect random personal questions to ask a guy.
1. Who in your life always stresses you out and who do you rely on to help you calm down?
2. What is a controversial opinion do you have?
3. What seemed normal in your family when you were growing up, but seems weird now?
4. Would you rather spend the day at an art, history, or science museum?
5. What holidays did your family really go all out for when you were growing up?
6. What was the most awkward conversation you ever had with someone?
7. What chokes you up when you think about it?
8. Where do you go when you want to be alone?
9. When was the last time you really panicked?
10. Which aspect of your life is going really well right now and which aspect could you use some help with?
11. Do you think any part of your personality needs to be improved?
13. If you see a homeless person asking for money, do you give them any?
14. What activity calms you down and makes you feel at peace with the world?
15. Do you think you could be with someone who is deeply religious?
16. Do you think gay people should adopt?
17. What thing do you regret the most in life?
18. What character trait do you love the most in people?
19. What thing do you want to avoid when being a parent?
20. Is marriage an important institution or just a piece of paper?
21. Is your career something you would want to do forever or is it something temporary?
22. Would you like to be a stay-at-home dad?
23. Did you want to have kids when you were a kid yourself?
24. Long-term relationships or causal flings?
25. What’s your view on religious differences?
26. If from somewhere different than you, what was it like growing up there?
27. What do you consider a red flag in a relationship?
28. What’s the most spontaneous thing you’ve ever done?
29. What’s the most embarrassing thing you’ve ever done to get a crush’s attention?
30. Do you think double texting is a big deal?
31. What’s the most cringeworthy outfit you’ve ever worn?
32. What do you wish you were really good at?
33. What does your ideal weekend look like?
34. When was the last time you felt most yourself?
35. What is the worst lie you’ve ever told your parents?
36. What is the biggest lesson you’ve learned?
37. Are you more of a morning or night person?
38. What is the one thing you can’t live without?
39. What is the last thing you searched for on your phone?
40. What three items would you bring with you to a deserted island?
41. How do you pick yourself up when everything seems to be going wrong?
42. If you could relive one moment of your life, which would it be?
43. What is something you appreciate, but often take for granted?
44. What makes you different from everyone else?
45. What’s something you’re glad you’ll never have to do again?
46. Have you ever made a decision that changed the course of your life?
47. Is there anything you wish you could change about your family?
48. What do people always get wrong about you?
49. Have you ever hooked up with someone of another gender?
50. What’s your favorite part of your typical day?
Random Questions to Ask a Guy Friend
Are you also a person who prefers a guy best friend over a girl best friend? If so, then here are some random questions to ask your guy best friend in order to learn more about him.
1. What gender stereotype do you wish the world would let go of?
2. What’s your relationship to your gender?
3. What do you want to be remembered for after you die?
4. Who do you feel most comfortable talking about your feelings with in your life?
5. What do you wish you had less of in your life right now?
6. Do you want to be more or less like your parents?
7. Do you believe in the concept of soul mates?
8. What would you like to do to me tonight?
9. What’s the hottest memory you have of us?
10. What’s a question you wish more people asked you?
11. What does self-care look like for you?
12. What do you want to do in retirement?
13. How do you deal with conflict in relationships?
14. How long does it take you to open up to someone?
15. What’s one thing I don’t already know about you?
16. If you had to eat only one meal for the rest of your life what would it be?
17. If you redesigned society, what would you change?
18. What would you do if you found out you had a year to live?
19. What do you think makes a meaningful life?
20. What three non-electric or non-automatic items would you take on a deserted island?
21. What is one accomplishment that you’re proud of?
22. Do you know how to play any musical instruments?
23. If you could change one decision you made when you were younger what would it be and why?
24. Do you think psychics are actually psychic?
25. Have you ever done something you regretted?
26. Do you think anyone has the capacity to cheat or do you think only cheaters cheat?
27. What’s the most intense experience you’ve had in your life?
28. When your parents get old, how do you plan on taking care of them?
29. Do you want to live near or far from relatives?
30. What do you look forward to about being a parent?
31. What was your favorite subject/class in school?
32. Would you rather a night in a fancy penthouse suite or a private beach house?
33. If you were on a dating game show, what questions would you ask?
34. Do you think people are made for each other?
35. Do you believe in true love or love at first sight?
36. Do you put as much effort and emphasis on inner beauty as outer beauty?
37. If you could change one thing about the way you look, what would it be?
38. When were you the most disappointed in yourself?
39. Would you consider yourself a pessimist or an optimist?
40. What do you see as your best character trait?
41. If you could pick a new “golden rule,” what would it be?
42. How often do you go out of your way to help someone?
43. What is the most important lesson to teach a child?
44. If it cost the same, would you live in a mansion or a mid-sized house with a lot of land?
45. Would you rather acquire material items or experiences?
46. What do you hope to achieve in the short-term?
47. Do you find praise or criticism to be more motivating?
48. What thought or object gets you through the day?
49. Who in your family do you view as a role model?
50. Do you think it’s better to save money or invest?
51. Do you have an older brother or sister?
52. What kind of an experience do you have with pets?
53. What’s your favorite way of traveling a foreign country?
54. What thing about your childhood do you miss the most?
55. In an ideal world, would you go for another drink?
Random Questions to Ask a Guy Crush
Butterflies in your stomach? We are pretty sure that you must have a scheduled meeting with your crush. Thus, if you want to hide your uneasiness and want to leave a good impression on him, get hold of these amazing random questions to ask your crush.
1. What’s the most impressive skill you have?
2. What’s the best gift you’ve ever received and who was it from?
3. What’s a typical Saturday look like for you?
4. What was the last show you binge-watched?
5. What part of the world would you love to travel to?
6. What is the nicest thing someone can do for you?
7. What is the kindest thing someone has ever said about you?
8. What do you think is your best quality?
9. What do you spend way too much money on?
10. What are you doing when you’re at your happiest?
11. If you were to choose a song you’ll have to listen to forever, what would it be?
12. If you took one day off to do anything you want, how would you spend the day?
13. If you had to rename yourself, what name would you choose?
14. If you could have any job you wanted, what would you choose to do?
15. If you could have a dinner date with anyone in the world, who would you choose?
16. If a genie grants you three wishes, what would they be?
17. Do you like huge parties, or would you rather spend time in a small group/alone?
18. Do you have a close relationship with your parents?
19. What’s the type of person do you enjoy being around the most?
20. What’s the one thing that drives you crazy about other people?
21. What do you wear when you sleep?
22. What’s the biggest deal-breaker on a date?
23. What is your preference – dating someone smart or hot?
24. What do you think the color of my underwear is?
25. What’s your favorite type of foreplay?
26. Can you sum up your life’s philosophy in one sentence?
27. Are your priorities different now than they were in the past?
28. If money wasn’t an issue, what would you do?
29. How do you calm yourself down when you are angry?
30. Do you think it’s easier to ask for permission or forgiveness?
31. Do you feel like you’re living life to the fullest?
32. If you ever need any advice, who would you ask?
33. If you could change anything in your life, what would you change?
34. If you can go back to do one thing differently in your past relationships, what would that be?
35. What would your younger self not believe about your life today?
36. Which part of my body would you want to kiss?
37. Which of my body parts appeals to you the most?
38. In your opinion, what makes humanity successful?
39. How would you describe your favorite color without the use of color words?
40. What parts of your life have improved in the previous 5 or 10 years?
41. What makes you feel the most nervous?
42. Do you prefer to hang out with introverts or extroverts?
43. What you rather be rich and single or poor and in love?
44. Do you think that there’s more to reality than what we see with our eyes?
45. What’s the type of person you enjoy being around the most?
46. If you could rewrite your past, what’s one thing you’d change?
47. What are your parents/step-parents/guardians/people who raised you like?
48. What’s your favourite song from your teenage years?
49. On a scale from 1 to 10, how good would you say you are at singing in public?
50. What’s the most significant love lesson you have learned?
5 Tips for Choosing Random Questions to Ask a Guy
As you been through a variety of questions, you might be wondering what is the criteria to select the right questions.
Fortunately, there is no particular method but following these tips for choosing random questions to ask a guy will make the process far more simpler. Get a load!
1. Thoughtful follow-up questions are the best way to show you are a good listener. Whenever somebody tells you something—anything—listen carefully and then follow up with some random questions to ask a guy that prompts a more in-depth explanation of what they just said.
2. When no one knows what to say, they discuss the weather. And believe us, it is the most cliché topic to discuss with any person on the first meetup, so try to avoid such random questions to ask a guy that revolves around topics like these if you don’t want the conversation to get dull.
3. Having a wonderful sense of humour adds to your already endearing personality! Obviously, you have zero idea about their kind of humour, but cracking a joke or making a pun can go a long way in the conversation.
Therefore, always make sure to keep the conversation light with random funny questions to ask a guy because these light hearted questions can work like a fun element in your conversation.
4. Know the answer to your questions. While this may seem weird, it is one of the best pieces of advice you will ever hear when it comes about random questions to ask a guy.
Whatever you ask, know your responses as well so that if the person in front of you is unable to respond, you can make them feel at ease with yours and keep the discussion continuing, or what if he backfired you with the same question? You must keep an answer in your mind for the safe side!
5. We all enjoy randomness, but too much randomness is difficult to keep up with, much like a youngster running from place to place. Find a happy medium, don’t get too hard with random questions to ask a guy and watch how your talks will become far more meaningful.
When looking for random questions to ask your crush, keep in mind that you don’t want to start with profound, hard-core queries. Yes, you can get deep into the conversation but wait till the other person gets the hang of it.
Final Thoughts on Random Questions to Ask a Guy
Who said your first conversation with any guy should be serious? Yeah, we do understand that not everybody is comfortable enough cracking jokes with the guy friends, but a little bit addition of the given random funny questions to ask a guy can make things a lot easier.
If you are talking to your guy friends, husband, fiancé, or crush, then these random questions to ask a guy will help you to learn more about them. It will shed some light on their past, childhood stories, and embarrassing moments and may reveal some secrets too.
Hence, before your conversation gets tedious, select the random questions to ask a guy from the above list and make this chat a conversation-to-remember.
Also, comment down below; what do you think was the best random question that one could ever ask a guy, and if you have tried any of them already, then do mention it below; how did the conversation go. It would be amazing to hear from you guys!