519 Random Questions to Ask a Guy to Keep Conversation Flowing

These random questions to ask a guy are best to start a conversation and pique curiosity. No matter if the guy is your friend, colleague, boyfriend, crush, family member or any stranger; random questions can help you to kickstart and continue your conversation.

We have enlisted different types of random questions to ask a guy for you which can help you in a lot of situations. The list varies from clean to dirty, serious to random funny questions to ask a guy. These questions will act as an icebreaker and will take your conversation to an intimate level. It will help you to have an amazing conversation with a guy and to become close to him.

Ask these questions and enjoy a mind blowing conversation!

Best Random Questions to Ask a Guy

These are some of the best random questions to ask a guy. They will act as conversation starters and will make your dialogue interesting. Try them and indulge in unique conversation.

1. What are some foods you would never eat? And why do you hate it?

2. What do you consider to be your most attractive physical feature?

3. What is it about me that you admire the most? And why?

4. What would you do if you could change jobs right now? Or are you satisfied with your current job?

5. Give me three words that best describe who you are.

6.  What is your ideal date type? And who do you prefer?

7. How did your best friend and you meet?

8. What do you enjoy most about your friends? And why?

9. Have you ever had a friend betray you?

10. Is there anything a lady can do that you will never forgive her for?

11. Can you tell me about the last time you cried? And why did you cry?

12. Do you prefer to work out at the gym or at home?

13. What is the most exciting vacation you’ve ever experienced? Do you want to experience it again?

14. Tell us about a country you’d like to visit.

15. Do you like to go camping or clubbing? Do you prefer my company for this?

16. What are your greatest fears? Is it a big deal for you?

17. Can you tell me about the nicest thing you’ve ever done for a woman?

18. What is the most thoughtful thing a woman has done for you?

19. What is your biggest dating obstacle? And why?

20. What is your earliest memory of childhood? Can you tell the story of it?

21. What is one item that consistently irritates you? And why?

22. What do you believe to be your most great achievement to date?

33. What do you like best about where you live?

24. What is one feature about your current location that you truly hate?

25. Do you have a favorite Starbucks order?

26. What would you acquire if you could only get one present?

27. Would you rather get a present, gift cards, or cash?

28. Do you consider yourself to be an introvert or an extrovert?

29. If you could go back in time and change one thing about your life, what would it be?

30. When you need to unwind, where do you like to go?

Good Random Questions to Ask a Guy

These good random questions to ask a guy are of different categories and will give you an idea of how to start and what to say while having conversation with a guy.

1. In a film about your life, who would you choose to play your love interest?

2. What do you consider to be the most difficult aspect of working every day?

3. Do you have any regrets till now?

4. Do you think it’s possible to fall in love at first sight?

5. Is there anything about your family that you wish you could change?

6. What is the strangest dream you’ve recently had? When did you plan to fulfill it?

7. Can you tell me about the worst lie you’ve ever told a girlfriend?

8. Do you know how to identify if someone is lying to you?

9. Do you believe that everyone has a single soulmate or that everyone has several soulmates?

10. Would you rather have the power to see through walls or the ability to read people’s minds?

11. What is your most appreciated feature?

12. Would you prefer to spend a Saturday night out with your friends or with a woman?

13. What is your most valued childhood possession?

14. Is there anything about you that you hope your mum never finds out about?

15. What is the strangest thing you’ve recently seen in the news?

16. Where have you ever kissed someone in the weirdest place?

17. When you’re bored, what do you daydream about?

18. What did you take for granted in your previous relationship?

19. Has anyone ever caught you naked in your house?

20. If you didn’t know me, how would you describe me to someone who didn’t know me?

21. What is a favorite family memory of yours? Can you tell me about this?

22. What is one of your favorite traditions?

23. Which reality show is your favorite? And why?

24. Who is your favorite Kardashian or Jenner?

25. Would you rather be a model or an actor if you had to choose?

26. Before you tried it, what did you think was silly?

27. Would you like to arrive at work early and leave early, or arrive late and leave late?

28. If you had to donate to one charity, what would it be?

29. If you were to make a movie about your life, who would you like to play your life role?

30. How many places have you traveled to?

31. Have you ever broken some law?

Fun Random Questions to Ask a Guy

Want to befriend a guy? Or want to update your friendship level with a guy? These fun random questions to ask a guy will let you have a lighthearted conversation with a man.

1. What you liked the most at your young age but now you feel silly?

2. What is the extremely stressed situation you have faced in life?

3. What would be the best pet according to you?

4. Have you ever played a prank on someone?

5. If you can throw up on someone who it would be?

6. Is there anything someone did selflessly to help you out?

7. What is your perfect burger?

8. If you can be a ghost for a day what will you do?

9. What is your favorite fictional villain character?

10. Is there any game or sport you find very boring?

11. If you can add a few more hours to your day how will you utilize it?

12. Is there any dream city of yours where you want to move in?

13. Do you get angry about some little things more than you should?

14. Which podcast do you like the most?

15. Do you like to watch horror movies?

16. What is your preference for a grand wedding or destination wedding?

17. What is the weirdest moment of your life?

18. Do you like driving?

19. What do you like the most, indoor games or outdoor games?

20. Do you like trekking?

21. Do you like girls wearing make-up?

22. Do you think you are mature enough according to your age?

23. Have you ever visited an old-age home?

24. What was the worst date you’ve ever been to?

25. If you could change your name what would it be?

26. If you ever write your autobiography, what would you name it?

27. Have you ever stacked anyone?

28. How much are you on social media?

29. Are you a daily news watcher?

30. If you get a chance to pet a wild animal what would it be?

31. What was your worst detention in school?

32. How many dating apps have you ever used?

33. Do you like to work in a group?

Cute Random Questions to Ask a Guy

Do you have any innocent male friends? Or, have you recently encountered any such guy? Yes? Then these cute random questions to ask a guy are best to have conversation with them.

1. What would you say is the difference between your present town and your hometown? Which one is your favourite?

2. How has your town changed over time, if he still lives there?

3. Are you happy with your current position? What is your ideal job? What would you change if you had your dream job?

4. What can you tell me about your friends? In a friendship, what do you value the most?

5. What do you look for in a film? Which movie is your current favorite?

6. What is your preferred method of visiting a foreign country? Camping or hotels that are expensive?

7. Who would play the lead role in your life if it were a movie, and why?

8. What kind of pet-owning experience do you have?

9. What three items would you bring to a desert island if you only had three?

10. How do you feel about social media? How long do you think you’d be able to go without it?

11. What are your key requirements when purchasing a phone? Brand, specifications, look, and personal recommendations?

12. Have you ever had a paranormal experience? Do you know for sure if they’re real or not?

13. What famous person would you wish to meet and why? Do they deserve to be admired?

14. Do you believe that reality show participants have self-respect?

15. What is your definition of karma? Have you ever come up with it?

16. How can you deny the existence of a higher power without concrete evidence?

17. What are your thoughts on police brutality? What do you want to convey?

18. What would be the one meal that you could eat for the rest of your life?

19. Even if you had a million dollars, what dinner would you refuse to eat?

20. What would you do if you won $10 million in the lottery?

21. Which era of history would you choose to live in if you could only live in one?

22. With which world leader would you like to drink tea?

23. Which of the ghosts would be the most fun to hang out with?

24. I’d like to know more about your hometown. What is something unique about it?

25. What’s it like to be a part of your family?

26. Do you have a nickname? If you do, can you tell me how you got it? Is it to your liking?

27. What would be the funniest thing to fill a piñata with?

28. What is the most pleasant sounding name for either a boy or a girl?

29. What’s the most nightmarish creature you can imagine?

30. Is there an area of life in which you’re jaded?

31. Have you ever wanted to be a vigilante?

32. Have you ever successfully gotten over an addiction?

Funny Random Questions to Ask a Guy

Is your conversation with a guy getting serious? Do you want to laugh with your crush or boyfriend? Yes? Pepper these random funny questions to ask a guy in your conversation and see the magic.

1. What are the crazy adventures you want to try in your life?

2. What is your favorite smell?

3. What is the best Wi-Fi name you have seen in your entire life?

4. Have you ever fallen off your bike in front of a huge crowd?

5. What is it that you keep wanting to smell despite the fact that it doesn’t smell particularly good?

6. Have you ever gone a day without wearing underwear?

7. If you can still remember, what are your funniest childhood memories?

8. How long do you think you’d survive in a zombie apocalypse?

9. If the roses are red, why are violets blue?

10. How do you hang toilet paper: over or under?

11. Have you ever gone to a corner store and stolen a candy bar?

12. How many beers do you think I’d be able to consume?

13. What would you do if you won a million dollars?

14. What is your Wi-Fi password?

15. Why is it that round pizzas come in square boxes?

16. Where was the most embarrassing place you have ever farted?

17. Has someone caught you dancing in front of the mirror?

18. If I will fail a driver’s test, in which part will I fail?

19. Have you ever tried talking to your dog?

20. What would you do if you could live forever?

21. What would you call a male ladybug?

22. Do you like pineapple on your pizza?

23. Have you ever been caught cheating on a test?

24. In your opinion, how long can my hair grow?

25. Can you show me the hidden apps in your phone?

26. Who was your first ever crush?

27. Do you sometimes hear certain voices in your head, too?

28. What are three items you might purchase at the grocery store to get strange looks from the cashier?

29. What’s the sexiest name you’ve ever heard?

30. Do you sleep with lights on or off?

31. What is the silliest thing you’ve ever seen a stranger do in public?

32. If you could have a superpower, what would it be?

33. What do you typically do when you’re bored?

34. What’s one thing your dogs could say that would completely ruin your image if they could talk?

35. What’s the most hilarious fact you know?

Interesting Random Questions to Ask a Guy

A person has a lot of personality aspects. Getting to know about his personality will make both of you intimate to each other. So, try these random interesting questions to ask a guy to have a serious and unique conversation with a guy.

1.  What was the last thing you created?

2. Who is a better cook your mother or grandmother?

3. What book do you wish would be turned into a movie?

4. Is there an app that you hate but use anyways?

5. What was the last thing that you fixed?

6. Could you survive in the wilderness for a month?

7. What are some songs you know by heart?

8. What piece of technology brings you the most joy?

9. What do your clothes say about you?

10. What’s your “going to bed” routine?

11. What animal best represents your personality?

12. If you could rename the street you lived on, what would you rename it?

13. What’s the fullest you’ve ever been?

14. What behaviors make you think a person is creepy?

15. Who in the movie business seems the most down to earth?

16. What’s the funniest or most amazing cell phone cover you have seen?

17. Which musical artist is greatly overrated?

18. What company or franchise do you wish would go out of business?

19. What’s the perfect temperature to set the thermostat at?

20. Who around you has the worst luck?

21. What’s your favorite sounding word?

22. What’s the weirdest thing that has happened to you in a car?

23. If you could fit your whole life into one picture what would it look like?

24. What’s something that can’t be found or bought on the internet?

25. What should the first colony on another planet be called?

26. What piece of clothing or accessory can someone wear that immediately?

27. What’s makes you have a bad opinion of them as a person?

28. If you put out a magazine, what would you name it and what would be in it?

29. If you were challenged to a duel, what weapons would you choose?

30. What villain do you really feel for?

31. What is the most interesting thing you could do with 400 pounds of cheddar cheese?

32. What did you think you were good at but are actually quite bad at?

33. What in a trailer automatically makes you assume a movie will be horrible?

34. What game do you wish you could act out in real life?

35. What are you really happy about being terrible at?

Random Questions to Ask a Guy Over Text

Suppose you are having a conversation with a guy over text. You are getting out of ideas of how to keep the conversation flowing. In this case, don’t panic. Take ideas from these random questions to ask a guy over text and ask them.

1. What is your favorite movie of all time?

2. How do you usually spend your weekends?

3. What is the most important thing you’ve learned in life?

4. What’s the most embarrassing thing you’ve ever said or done in front of someone you liked?

5. What’s the last concert you went to?

6. What are your hidden talents?

7. What word would you use to describe yourself if you had to choose only one?

8. What has been your most memorable life experience to date?

9. What is the most amusing thing that anyone might spend money on or purchase on the internet?

10. What’s the weirdest thing that happened to you this week?

11. What is your pet peeve?

12. Do you like pets?

13. When was your last relationship?

14. Where is your dream travel destination?

15. What food do you usually enjoy eating?

16. What was the most meaningful gift you’ve ever gotten?

17. What is your favorite childhood memory?

18. What weird smell do you find particularly appealing?

19. What are some things you wish you had known when you were younger?

20. How do you deal with people who annoy you for no apparent reason?

21. Where would you live if you could live anywhere in the world?

22. What kinds of stuff makes you laugh the hardest?

23. Do you believe in love at first sight?

24. What movie did you watch over and over when you were a kid?

25. Who do you consider to be the luckiest person in this world?

26. Who haven’t you seen or spoken with in a long time who you hope is doing well?

27. What qualities do you look for in a future partner?

28. What is your all-time favorite movie quote?

29. What are some of the questions you wish people would stop asking you?

30. What’s your favorite meme of all time?

31. What’s the worst text you’ve ever sent by accident?

32. Who is your celebrity crush?

33. Which animal would you like if you could be one?

34. If you could be a superhero, who would you be?

35. When was the last time you did something that took you out of your comfort zone?

Random Questions to Ask a Guy You Like

Do you love a guy? Wish to spend a lot of time with him to become intimate with him? I have heard you! Try these random questions to ask a guy you like and best of luck!

1. When is your birthday?

2. How many siblings do you have?

3. Who is your favorite sibling?

4. Would you like to get married?

5. Would you like to have kids? If so, how many?

6. What is your greatest fear?

7. Where do you see yourself in five years?

8. How do you measure or define success?

9. Are you religious?

10. Is it easy for you to make friends?

11. What is the most unhealthy habit you have?

12. Have you ever experienced some sort of abuse?

13. What is one thing you can never compromise on when it comes to relationships?

14. What is your greatest personal value?

15. Have you ever written a published piece of work?

16. Do you think tertiary education is necessary?

17. Have you ever been emotionally affected by a band splitting up?

18. Would you consider gambling?

19. Have you ever thought of starting a new life somewhere?

20. Do you ever feel like an outcast?

21. Has anyone in your family been directly affected by war?

22. How would you describe the relationship you have with your parents?

23. Have you ever had a sequence of things going wrong for you?

24. Have you ever participated in a ritual or a ceremony of any kind?

25. Do you think any job/profession is beneath you? If so, what is it?

26. Have you ever bullied someone?

27. Are you proud of your family?

28. Do you ever feel like your family is trying to pull you down?

29. Have you ever argued with your significant other in public?

30. Have you ever physically hurt anyone?

31. Is it important to you that people remember your birthday?

32. Do you ever feel like there’s nothing left to do in life?

33. Would you say you’re good at managing money?

34. Have you ever doubted your own sanity?

35. Did you ever talk back to your parents when you were a kid?

Random Questions to Ask a Guy to Get to Know Him

Have you met a stranger? Want to have a conversation with him? Try from these random questions to ask a guy to get to know him to start a conversation and to befriend him.

1. How old are you?

2. What is your star sign?

3. What is your favorite color?

4. What is your favorite music genre?

5. What is your fashion taste?

6. What three words best describe you?

7. Do you enjoy spending time alone?

8. Do you consider yourself a gamer?

9. What is your favorite decade of music?

10. If you could invite one artist to your wedding, who would it be?

11. Is there a fictional character you’d want to be more like?

12. Would you rather have someone act hostile to your face or pretend that they like you?

13. How does a rainy day make you feel?

14. What’s your favorite type of exercise?

15. Who is your favorite athlete?

16. Which college did you go to?

17. What were your majors in school?

18. Did you ever cheat on an exam?

19. What career path are you pursuing?

20. Were you excited to start working when you were finishing school?

21. Have you ever suffered for being different?

22. Would you consider dumpster diving?

23. Would you say you’re closer to your parents or grandparents?

24. What is your favorite local restaurant/cafe?

25. Do you try to support local businesses over large corporations if you have a choice?

26. What really pumps you up and gets you going?

27. What’s one thing you do regularly and would never skip?

28. What are your thoughts on thrifting?

29. What’s one tourist attraction you’d love to visit the most?

30. Do you prefer simple food, or would you rather go for interesting combinations of flavors?

31. How do you feel about getting pranked?

32. Do you often get embarrassed for other people?

33. Do you prefer games in which you cooperate or play against one another?

34. What was your first car?

Deep Random Questions to Ask a Guy

These are some random deep questions to ask a guy which will help you to peek into his personality and know about his moral values and perspectives. Ask these questions during your conversation to know about your differences and similarities.

1. Do you consider yourself an introvert or an extrovert?

2. What are you most thankful for?

3. Which parent are you closer to and why?

4. What are your thoughts on online dating or tinder?

5. What’s on your bucket list this year?

6. How would you describe your best friend?

7. What do you think of best friends of the opposite sex?

8. What makes you feel accomplished?

9. How do you feel about sharing your password with your partner?

10. What was the best phase in your life?

11. Would you still love your spouse if they were diagnosed with a terminal disease?

12. What qualities do you admire about your parents?

13. What are some of your favorite songs?

14. What was the worst phase in your life?

15. What is the craziest thing you’ve ever done and would you do it again?

16. If a genie granted you 3 wishes right now, what would you wish for?

17. Does your job make you happy?

18. What’s the one thing you would like to change about yourself?

19. Would you ever take back someone who cheated?

20. What is a relationship deal breaker for you?

21. Are you more into looks or brains?

22. When do you think a person is ready for marriage?

23. Is what you’re doing now what you always wanted to do growing up?

24. Have you ever lost someone close to you?

25. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?

26. What’s the one thing that people always misunderstand about you?

27. What is your idea of a perfect vacation?

28. When was the last time you broke someone’s heart?

29. Would you relocate for love?

30. What did you want to be when you were younger?

31. What kind of parent do you think you will be?

32. Do you judge a book by its cover?

33. What’s your biggest regret in life?

34. Who is that one person you can talk to about just anything?

35. What’s an ideal weekend for you?

36. Are you religious or spiritual?

Flirty Random Questions to Ask a Guy

Do you want to have spicy conversations with your crush, boyfriend or spouse? Then pepper your conversation with random flirty questions to ask a guy and make your dialogue interesting.

1. Would you rather be considered sexy or smart?

2. What is something about you that would surprise me?

3. What did you first notice about me?

4. What was your first kiss like?

5. What’s one question you’re dying to ask me?

6. How many times have you been in love?

7. What do you think about before you fall asleep?

8. So what do you think we should do this weekend?

9. Do you enjoy being in a long term relationship?

10. If yes, what do you most like about being in a relationship?

11. If you could be famous for anything what would it be?

12. What’s a gift you’ve always dreamed of receiving?

13. When are we going on our next date?

14. What puts you in a good mood?

15. Would you rather that I was naughty or nice?

16. Have I made it into any of your dreams yet?

17. What is a favorite movie of yours that I would be surprised that you like?

18. What wins you over more… brains or beauty?

19. Would you rather end a date with a kiss or with a little bit of mystery?

20. What have you always imagined doing with a girlfriend that you’ve never done?

21. If you had to use one movie title to describe your kissing style what would it be?

22. Little spoon or big spoon?

23. What is one temptation you can never resist?

24. How would someone usually let you know that she likes you?

25. Do you like a woman that is soft and sweet or more assertive?

26. How would you describe yourself in 3 words?

27. How would you describe me in 3 words?

28. Do you prefer staying in or going out?

29. What do you think your best feature is?

30. Have you ever made a really romantic gesture?

31. Would you rather date someone smart or hot?

32. How many people are you crushing on right now?

33. What’s the farthest you’ve gone on a first date?

Dirty Random Questions to Ask a Guy

Want to have some juicy conversation with a guy? These dirty random questions to ask a guy will make it sexy! Ask these questions to your spouse, boyfriend and crush.

1. What is your favorite place to be massaged?

2. What is your sexy scene from a movie?

3. Do you have any fetishes?

4. Have you ever had a one-night stand?

5. What’s the weirdest place you’ve ever done it?

6. Do you like it when someone pulls your hair?

7. Where is the naughtiest place you have done it?

8. Do you get amorous in the morning or evening?

9. What are you best at in bed?

10. Have you ever done it outside?

11. What’s the best bedroom experience that you’ve ever had?

12. What do you think about dirty talk?

13. Is there anything that turns you off in the bedroom?

14. What’s the longest you’ve gone without doing it?

15. What’s the most number of times you’ve done it in a row?

16. What’s one public place where you would want to do it?

17. Have you ever had a friend with benefits?

18. If I were in your room right now, what would you want to do to me?

19. What is your favorite sex position?

20. What’s the sexiest thing someone could say to you in bed?

21. When do you feel the most passionate?

22. What is your dirtiest fantasy?

23. What are your thoughts on foreplay?

24. What do you think about friends with benefits?

25. Do you like the lights on or off during sex?

26. What do you think about toys in the bedroom?

27. What would you do if you could do anything with me?

28. When did you lose your virginity?

29. What is the weirdest thing you have dreamt about doing with a girl?

30. Are you a top or bottom?

31. What is the first thing you noticed about me?

32. Do you like when the girl makes the first move?

33. What turns you on?

34. What do you find most attractive in a girl?

35. What is the craziest thing you have ever done?

Personal Random Questions to Ask a Guy

Asking personal questions is a great way to befriend someone! It lets others open up themselves and build trust in you. So, do try these random personal questions to ask a guy and know about his life.

1. What’s been your highest point in life so far?

2. What’s been your lowest point in life so far?

3. What makes you emotional?

4. What makes you stressed?

5. Do you believe in a higher power?

6. If you had the power to know the date of your death, would you want to know?

7. What are you most grateful for?

8. Is there anything you would change about yourself if you could?

9. Who inspires you the most?

10. Does being rich and famous appeal to you?

11. What’s the biggest risk you’ve ever taken?

12. What’s the biggest thing you’ve ever given up?

13. What’s the angriest you’ve ever been?

14. What’s the nicest thing you’ve ever done for somebody?

15. How would you describe your childhood?

16. Do you have any unresolved issues with your family?

17. How do your best friends describe you?

18. Do you trust easily?

19. What’s a secret you’ve never told anybody?

20. What did you learn from your last relationship?

21. How many girls have you told “I love you”?

22. Have you ever cheated in a relationship?

23. What is your greatest life goal?

24. What do you want for yourself in five years? In 10 years? 25 years?

25. Do you see me in your future?

26. How often do you feel overwhelmed?

27. What will immediately disqualify a potential SO?

28. How adventurous are you? Give some examples.

29. Who do you want to be more like?

30. When was the last time you really panicked?

31. Where do you go when you want to be alone?

32. What chokes you up when you think about it?

34. How politically involved are you?

35. What is a controversial opinion do you have?

36. What fact do you try to ignore?

37. If you see a homeless person asking for money, do you give them any?

Random Questions to Ask a Guy Friend

These random questions to ask your guy best friend are best when you are hanging out with your male friends or having fun with them. It will keep a flow in your conversation.

1. If there were internet Olympics, what sports would be in it?

2. What is the most interesting game concept you can come up with?

3. If the police raided your house right now, what is the most incriminating thing they would find?

4. What actor played their character so well that you can’t watch them in any other show or movie without seeing that character?

5. What is the most fun thing someone could have in their backyard?

6. If you had to break one world record in order to receive one million dollars?

7. What world record would you try to break?

8. What first world problem do you have?

9. What would be put inside a mental health first aid kit?

10. What conspiracy theory do you actually believe?

11. What looks delicious but tastes terrible?

12. What three activities would you rate 10/10 would do again?

23. What has your hardest goodbye in life been so far?

24. What’s the last lie you told?

25. What’s the best compliment you’ve ever received?

26. What do you consider the ultimate comfort food?

27. What do you consider your best physical feature?

28. What are the top three things that stress you out?

29. What are the top three ways you deal with stress?

30. When was the last time you were jealous and why?

31. If you could only have three things on your life bucket list, what would they be?

32. What’s the worst decision you’ve ever made?

33. What’s something you’d consider unforgivable?

34. If you choose to get married one day, what would your dream proposal scenario be?

35. What’s the most loved you’ve ever felt?

36. What would your dream home look like?

Random Questions to Ask a Guy Crush

Do you want long and interesting conversations with your crush? Want to spend quality time with him? I know you have the desire for it. Go for these random questions to ask your crush to fulfill your desire.

1. Are you a dog or a cat person?

2. Are you more of a morning or night person?

3. Are you registered to vote?

4. Can you describe yourself in 3 words?

5. Can you keep it a secret?

6. Describe your ideal type in 5 words

7. Do you believe in love at first sight? How about soul mates?

8. Do you have a close relationship with your parents?

9. Do you have an extended family? How often do you see them?

10. Do you have any personal milestones?

11. Do you have any siblings?

12. Do you keep in touch with your childhood friends?

13. Do you know how your parents met?

14. Do you like cooking?

15. Do you like huge parties, or would you rather spend time in a small group/alone?

16. Do you live by yourself?

17. Do you work out a lot?

18. Have you been in a serious relationship before?

19. Have you broken someone’s heart before?

20. Have you ever been cheated on?

21. Have you ever been in love?

22. Have you ever been to another country?

23. How are you so good at your job?

24. How did your last relationship end?

25. If a genie grants you three wishes, what would they be?

26. If any actor or actress could play you in a movie, who would it be?

27. If you could ask me one question, and I had to answer truthfully, what would you ask me?

28. If you could have a dinner date with anyone in the world, who would you choose?

29. If you could have any job you wanted, what would you choose to do?

30. If you had to choose -would you rather find the Love of your life or be a Millionaire?

31. If you had to rename yourself, what name would you choose?

32. If you took one day off to do anything you want, how would you spend the day?

33. If you were to choose a song you’ll have to listen to forever, what would it be?

34. Is there anything you’re wondering about me?

35. Tell me one memory you cherish from childhood?

5 Tips for Choosing Random Questions to Ask a Guy

These random questions to ask a guy are best to know someone, keep the conversation going and to intimate you with the other person. But, there are some rules to have conversation with anyone. If you will keep these rules in your mind while asking these random questions in your conversation, you can achieve your goals easily.

So, let’s start with these tips.

Converse in a natural way:

Don’t start an interview with the guy by rapid firing these random questions. Keep your conversation natural, and occasionally pepper these questions to keep a flow.

Ask according to your relationship with the guy:

The random questions to ask your crush can’t be asked to a random person. You can’t ask juicy and flirty questions to a guy you just met. This will give a negative image of yours. Start with simple and general random questions and gradually go to intimate questions. Don’t rush your conversation!

Remain active during conversation:

Listen keenly to another person and show interest in the conversation. When he asks you questions, reply to him in detail.

If you want him to befriend you, make your tone friendly. If you want to know about him, tell him about yourself too.

Make your conversation interesting:

Add interesting or random funny questions to ask a guy to make your conversation interesting. When the guy will laugh with you or have fun with you, he will automatically relax and will talk openly. If you keep your conversation boring or serious, the person will ultimately become annoyed and bored. So, it is imperative to add fun elements in your conversation.

Observe your surroundings:

To keep your conversation natural and to come up with creative random questions, observe your surroundings. Observe the weather, people or things around you and ask questions related to them. It will keep your mind open and your conversation will keep its flow.

Final Thoughts on Random Questions to Ask a Guy

Random questions to ask a guy will help you in icebreaking and improving your conversation skills. These questions will support you in conversation when you will run out of ideas.

These questions are of different types and will help you in different types of conversation. The list has attempted to cover almost all aspects of your conversation.

Just keep the tips in your mind while asking random questions. Don’t use those random questions to ask a guy which will make him uncomfortable or will embarrass you in front of him. Remain calm and open minded while having conversation.

If you get nervous, try to cover it with random funny questions to ask a guy as it will make your conversation light. Making another person laugh will involve him in conversation, and maybe it will take both of you to upper levels of relationship.

So, have you decided to give these questions a chance? Right choice! Go for it now!

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