20 Questions to Ask a Guy: Funny | Deep | Dirty |

Got a crush on a guy you know?

Maybe he’s a co-worker, or a classmate, or even some guy you met out in the world?

Whoever he is, You probably want to know more about him.

Keeping that in mind, here we are with 20 questions to ask a guy to kickstart the conversation and help you get to know him better.

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20 Questions to Ask a Guy

  1. What’s the most pleasant thing you’ve ever heard about yourself?
  2. Which would you rather be, elegant or happy, and why?
  3. You can have one extraordinary power and only one. What is it, and why did you pick it?
  4. You get to marry one imaginary character – who is it?
  5. If you didn’t have to worry about money or a job, where would you live in the universe?
  6. In your mind, what are your 3 biggest defective qualities?
  7. Would you give attention to your brain or heart?
  8. What’s your weirdest peevish in a personal way?
  9. What’s the embarrassing and most awkward moment of your life so far?
  10. If you could have any job in the universe, what would it be?
  11. What’s your favourite type of music and rhythm to listen to?
  12. If you had to give me a nickname or humorous name right now on the spot, what would it be?
  13. Do you think it’s possible that we met in an existing life?
  14. How would you narrate me to someone who doesn’t know me?
  15. Which describes your personality… typical or nice?
  16. If you had the ability to read someone’s mind, whose would it be?
  17. Would you like waking up early or staying up late?
  18. What’s the funniest strange thing that’s ever happened to you?
  19. Pick one to live in: beach, city, village or country?
  20. What would you do in a day if you were told you only had a day to live?

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20 Dirty Questions to Ask a Guy

Communicating is an essential part of an intimate, romantic relationship. This can sometimes include naughty conversations. Whether you are getting to know a guy or you are in a committed relationship, you might feel the need to ask him some dirty questions.

So here we are with 20 dirty questions to ask a guy to spice up your relationship.

  1. What kind of attire would you like to see me in?
  2. What is your biggest hallucination?
  3. Do you like the lights on or off?
  4. What do you want to do to me right now in the present moment?
  5. Do you like it when I am naughty and playful with you?
  6. Have you ever dreamed about me during your sleep?
  7. Do you ever fantasize about me?
  8. Would you ever do the deed outside?
  9. What is your favourite kind of foreplay in Sex?
  10. Where is the fractious place that you have done it?
  11. Have you ever bought lingerie or sleepwear dresses for a girl?
  12. What is the best thing that a woman can do to you in the bedroom?
  13. What would you like me to say to you while we are in bed?
  14. Do you tend to give or receive?
  15. What curious thing that turns you the most?
  16. What do you think is stunning about me?
  17. What is the hottest attire that you have ever seen on a woman?
  18. What is your Dangerous fantasy?
  19. Do you prefer to be rough or romantic and sensual or passionate?
  20. If you could have any giant, who would you choose?

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20 Sexual Questions to Ask a Guy

Knowing the answers to some of these sexual questions will help you figure out if you and your guy are on the same page in terms of intimacy.

  1. What are you wearing right now? The fewer clothes, the better that enhance our mood.
  2. What would you do if you saw me naked?
  3. Would you like me to give you a therapeutic massage?
  4. What would you ask me to do for you when we met?
  5. Do you want me to talk flirty?
  6. Where do you want to kiss me?
  7. What was the last Sexy dream you had?
  8. What colour lingerie do you think I am wearing?
  9. Is there a position that you would like to try with me, but have not done yet?
  10. Do you like it when I am in control or do you tend to take the lead?
  11. What do you prefer I should wear to bed?
  12. Would you ever want to have threesome foreplay?
  13. What do you think is the sexiest and exciting thing about me?
  14. How do you like to be touched crazy?
  15. If you could only touch me in one place, where would it be?
  16. Will you unhook a bra with one hand?
  17. Have you ever been caught in the deed?
  18. What would you do to me if I am in your bed right now?
  19. Do you like to talk dirty during Sex?
  20. What would you like me to say to you while we are in bed?

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20 Funny Questions to Ask a Guy

Looking for funny questions to ask a guy to make him laugh? These questions can truly be hilarious to ask the guy you like!

Here are the top 20 funny questions to ask a guy you like.

  1. If you were in Jurassic Park, how long would you have survived especially in spite of danger or hardship?
  2. What is the unattractive thing you own?
  3. If you were forced to create a new dance step, what would it be and what would you call it?
  4. If you could be a woman for one day, what would you do in that whole day?
  5. What is the weirdest nickname people called at you?
  6. What would people hear if they could read your mind?
  7. What would you do if you won the lottery ticket?
  8. If you could commit any offense and get away with it, what would it be?
  9. If you could see the future, what would you desire to see yourself doing in 6 years?
  10. What was your most weird moment when you were in school?
  11. What TV show personality is most like you?
  12. Do you have any some unhappy experience Scar?
  13. Do you think ghosts actually exist?
  14. How would you spend a week if you could do anything you hope for?
  15. Who is your funniest and best friend?
  16. Do you like being tickled by friends?
  17. What’s your favourite chat up line?
  18. What weird smell do you really enjoyed ever?
  19. What’s the most polarizing question you could ask a group of your friends in a get-together?
  20. If animals could talk, which would be the rudest animal?

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20 Good Questions to Ask a Guy

When it comes to knowing about the guy you are interested in, it’s important to have strong, cute and interesting questions to ask him to help to the bond between the two of you develop.

Here are 20 cute and good questions to ask a guy during your conversation.

  1. What makes you twinkle to smile at?
  2. If there is any place in the universe that you could go, where would it be and why?
  3. What is your favourite sport in the world to watch/play?
  4. If we were dating, how would you celebrate our first year anniversary?
  5. What are your family personalities like?
  6. What about yourself do you find the most pride and pleasure in?
  7. Have you ever cried at a movie?
  8. What’s your favourite car and bike?
  9. What is the craziest and funniest thing that you have ever done in your life?
  10. What is your favourite romantic and craziest activity?
  11. What was the scariest alarming moment in your life?
  12. Who was your first crush in your lifetime?
  13. Who is your biggest hero or treasure?
  14. Would you like to hang out and chill out with me more often?
  15. What is your definition of intimate and faithful?
  16. Most embarrassing and weird look?
  17. What’s your favourite way to spend a rainy shower day?
  18. What’s your Favourite time of the year?
  19. Name a few things on your bucket list in your lifetime?
  20. What makes you highly nervous?

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20 Fun Questions to Ask a Guy

It can be hard to think of fun questions to ask a guy. Here are 20 fun questions to ask a guy, they cover all kinds of different subjects. I am sure you gonna like it.

  1. What was the funniest way that you have been harmed?
  2. If your life was a movie, what songs would be on the soundtrack album?
  3. What scene or incident from a TV show will you never forget?
  4. What Television entertainer catch phrase do you most enjoy using?
  5. What terrible and dreadful movie do you love?
  6. What song do you have to sing along with whom? When you hear it?
  7. What golden age are we currently living through in our life?
  8. If you had to become an inanimate object for a year, what object would you choose to be for?
  9. If you were a DJ, what would your DJ name be?
  10. Which movie do they need to broadcast to?
  11. What would be the most ironic way that someone could die in their life?
  12. Which reality TV show would you most like to see?
  13. What is the most unprofessional thing you’ve seen someone do?
  14. You can have one secret video/audio feed from anywhere in the world. Where do you telecast it?
  15. The last thing you ate is now the only thing you could eat it. How soon do you die?
  16. If you have a logo instead of a name, how would it look like?
  17. You are about to get into a fight with an opponent, what song comes on as your soundtrack?
  18. What would you name your boat if you had a boat of your own?
  19. Which fictional character would be the most boring to meet in your real life?
  20. If you had to change your name, what would your new name be, and why would you choose that name?

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20 Deep Questions to Ask a Guy

One of the ways to test intellectual compatibility is to ask questions. To ask your boyfriend deep questions means you are essentially seeing how well he keeps up with the important thing.

So here is the list of 20 deep questions to ask a guy.

  1. If you could fix one world problem, what could it be?
  2. If you could live in any era, which would it be and why so?
  3. What advice would you give to a person who is just graduating from high school?
  4. If you could have chosen your own name, what would you have picked up?
  5. If your home was on fire and you only had time to grab 5 things, what would they be?
  6. If you became a famous celebrity, would you enjoy the limelight or miss your privacy?
  7. If you had $400 to spend on something special just for you, what would you buy?
  8. If you had five wishes, what would they be?
  9. If you were told you have a terminal illness, how would you react to the news?
  10. If you only had a week left to live, what are the first things you would do?
  11. Would you sacrifice yourself for a stranger person?
  12. If a family member needed a kidney and you were the only match, would you give one up happily?
  13. If I wanted a puppy for my birthday as a gift, would you adopt a purebred from a breeder or a mix from a shelter?
  14. When you suspect that your neighbours may be abusing their child; do you mind your own business or call the police?
  15. If I went missing, my body never recovered, would you move on or devote your life to looking for me? If you did move on, how long would you wait in your life?
  16. If you could invite 5 people for dinner, who would they be?
  17. If you could live till you were 90 and have the mind or body of a 30-year-old, which would you choose and why it so?
  18. If you could wake up tomorrow and have gained one ability of power, what would it be and why?
  19. If a crystal ball could tell you the truth about your future life or me, what would you want to know?
  20. If you could live anywhere in this universe, where would you live?


So, these are the top 20 Questions to Ask a Guy.

However, this is just a basic idea of how you should go ahead with different questions and take them as a conversation starter.

In the end, it all depends on the situation, meaning the questions should be asked according to the circumstances you are in.

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