Now Reading
500 Random Questions to Ask a Guy to Know Him Better

500 Random Questions to Ask a Guy to Know Him Better

Updated on Oct 19, 2022

Reviewed by Julianne Cantarella, MSW, LSW , Certified Relationship Coach

500 Random Questions to Ask a Guy to Know Him Better

When you are on a date with someone you like, one of the last things you want to discuss is something boring like the weather. Do you think this is great? Probably NO. 

When you are in doubt about what to ask and what not, there are plenty of random questions to ask a guy to get into a more interesting and exciting conversation going to keep both of you connected.

These questions are great to ask when you are still getting to know someone, if you are on a first, second or third date with a guy or you are trying to know a little more about him. 

They are also great to keep in mind even if you two have been dating for a while and you just don’t have anything more to talk about over dinner. 

You can learn more about each other and probably open the door to more intimate discussion. Here is the list of random questions to ask a guy next time when you feel stuck. Some of them are funny and flirty while some are deep and personal. 

Every guy is different, therefore, pick the questions you think will work in your case and you really want to know the interesting answer. Scroll down to the bottom we have got waiting for you!

500 Random Questions to Ask a Guy to Know Him Better
500 Random Questions to Ask a Guy to Know Him Better

Random funny questions to ask a guy

Funny questions are always a necessity since who doesn’t want to laugh and have fun. Whether it’s your first date or wedding anniversary, fun talks boost the mood. By asking fun question to a guy he will come to know about your sense of humor as well. 

When he gets to know about it, he will never hesitate or be frightened of a blunder or anything else. This way you will build trust due to your genuine and funny character. Here is a list of fun questions to ask a guy

  1. What is your all-time favorite film that you’ve seen a thousand times?
  2. When you were a kid, what did you want to be when you grew up?
  3. If money were no object, where would you travel on vacation if you could go any place in the world?
  4. How would you spend a million dollars if you won the lottery?
  5. What about a woman appeals to you the most?
  6. What is your most shocking ability that you adore the most?
  7. What is one thing about you that everyone usually gets wrong?
  8. How do you unwind after a long, tiring day?
  9. Who do you look up to as a role model? Do you have any role models?
  10. Which celebrity do you most wish to meet?
  11. Is there anything you’ve never been really excellent at?
  12. What is the one thing about a woman that you always notice first?
  13. Which of your childhood memories is your favorite?
  14. What are you most proud of in your life that you have done so far?
  15. What have you done that you’re not very pleased with?
  16. Can you tell me about the scariest thing you’ve ever done?
  17. If you could be a pro athlete in any sport, which one would you choose?
  18. Who would you marry if you could marry only one celebrity?
  19. What is your best friend’s favorite that you adore?
  20. What do you consider to be the best aspect of being in a relationship?
  21. Which animal is your favorite? And why?
  22. Is there anything on your bucket list that you’d like to cross off as soon as possible?
  23. What’s something on your bucket list that you don’t think you’ll ever do?
  24. What’s the strangest thing that’s ever happened on a date to you?
  25. On your CV, what do you always lie about?
  26. Which show do you think you could binge-watch multiple times?
  27. What’s your favorite way to flirt? Can you show me how?
  28. On a first date, what would be the worst thing that could happen to you?
  29. Who would you like to meet if you could meet one dead celebrity?
  30. Who is your favorite Instagram user to follow? And why?
  31. What are your worst dating pet peeves?
  32. If you could change one thing about social media, what would it be?
  33. What is one thing a woman can do to impress you right away?
  34. What has been your most humiliating experience on date?
  35. What is one thing a lady may do to turn you off instantly?
  36. What’s the best praise you’ve ever received?
  37. What brings a smile to your face even when you’re having a bad day?
  38. Do you prefer to spend the rest of your life with dogs or cats?
  39. Tell me something that no one else knows about you.
  40. As a kid, what was your favorite candy or treat?
  41. What food would you be if you could be any food, and why?
  42. Do you believe that in the future more apes will become humans?
  43. Would you prefer to be the one to lead the relationship or have someone else lead it?
  44. Who is the one person in the world that you would marry, kill, and kiss?
  45. What’s the funniest joke you’ve ever heard about yourself?
  46. What’s the most amusing thing you’ve ever done with your friends?
  47. Have you ever had to use the restroom in front of a girlfriend?
  48. Have you ever had to wait a long time to use the restroom on a first date?
  49. Have you ever canceled a date? If so, then why did you do that?
  50. How long do you spend every morning getting ready?
  51. Why did the concept of “beta guys” become popular in our culture?
  52. Right now, who is someone you’d like to marry? Can you tell me about her?
  53. What is one item that you must place in your bathroom drawer?
  54. What’s the most embarrassing thing you’ve ever done in front of your mother?
  55. In a deathmatch, God or the Devil, who would win?
  56. What personal questions should a new friend avoid? And why?

Best random questions to ask a guy

Every conversation is the due for every good foundation. Guys might hesitate at first but they also like to share their stories of life. It’s just a misconception that only girls like to tell stories, however, the key is you have to ask the great question and be patient and warm towards the guy.

Here are the best questions which you ask a guy to make the conversation engaging and to get to know him better. 

  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. What is the most exciting vacation you’ve ever experienced? Do you want to experience it again? 
  8. Tell us about a country you’d like to visit.
  9. Do you like to go camping or clubbing? Do you prefer my company for this? 
  10. What are your greatest fears? Is it a big deal for you? 
  11. Can you tell me about the nicest thing you’ve ever done for a woman?
  12. What is the most thoughtful thing a woman has done for you?
  13. What is your biggest dating obstacle? And why? 
  14. What is your earliest memory of childhood? Can you tell the story of it? 
  15. What is one item that consistently irritates you? And why? 
  16. What do you believe to be your most great achievement to date?
  17. What do you like best about where you live?
  18. What is one feature about your current location that you truly hate?
  19. Do you have a favorite Starbucks order?
  20. What would you acquire if you could only get one present?
  21. Would you rather get a present, gift cards, or cash?
  22. Do you consider yourself to be an introvert or an extrovert?
  23. If you could go back in time and change one thing about your life, what would it be?
  24. When you need to unwind, where do you like to go?
  25. Do you prefer to work out at the gym or at home?
  26. Can you tell me about the last time you cried? And why did you cry? 
  27. Is there anything a lady can do that you will never forgive her for?
  28. Have you ever had a friend betray you?
  29. What do you enjoy most about your friends? And why? 
  30. How did your best friend and you meet?
  31. What is the first question you ask a woman on a first date?
  32. Do you want to start a family? Or is it your last plan? 
  33. What makes you wish to start a family if you want?
  34. What’s the worst situation you’ve ever found yourself in?
  35. Would you prefer a beach vacation or a vacation in a cool city?
  36. Do you have a favorite book? Can you tell me its name? 
  37. Tell me about the worst movie you’ve ever seen.
  38. What superpower would you like to have? How would you use it? 
  39. What is the most enjoyable activity you have ever shared with your friends?
  40. Do you have a stronger bond with your mother or father?
  41. Who in your family is your favorite? And for what reason? 
  42. What do you consider to be your most outstanding achievement?
  43. Can you tell me about your strangest habit?
  44. What is your biggest happy moment till now? 
  45. Is there anything on which you would never spend money?
  46. Do you have a yearly tradition that you look forward to?
  47. Do you prefer the winter or the summer?
  48. Can you think of a time when you were worried about something that turned out to be unimportant?
  49. What do you believe indicates a lot about a potential date?
  50. Have you ever had a crush on someone who didn’t match your feelings for you?
  51. How do you know when a woman is ready to meet your family?
  52. What would you do if you had a day off with nothing to do?
  53. Do you believe your zodiac sign is correct for you?
  54. Have you ever experienced the loss of someone close to you?
  55. What three wishes would you make if you had three wishes?
  56. When you were a kid, what was your favorite cartoon?
  57. What is the most disgusting food you’ve ever consumed?
  58. Would you want to play a game of truth or dare?

Random questions to ask a guy you like over text

Many people get stuck when it comes to face to face conversation, it can be because they are not used to it and it just seems way more intimidating than talking through a screen.

Therefore, some prefer to talk over text and they probably reveal their thoughts and secrets through it. Therefore, here are some of the questions to ask a guy over text while he is an introvert or extrovert. 

  1. What have you been doing incorrectly for the most of your life and only recently discovered the correct method to do it?
  2. Have you ever met a famous person? How did you feel? 
  3. Do you consider yourself to be a competitive individual?
  4. What is your favorite restaurant? Do you like to visit there with me? 
  5. What would you learn if you had the opportunity to learn a new skill right now?
  6. Do you have a favorite music that always brings back memories for you?
  7. If you could only listen to one song on repeat, what would it be?
  8. Is there anything you believe everyone should do at least once in their lives?
  9. What is something you’ve always wanted to do with a partner but have never done?
  10. What do you believe would be the most romantic vacation?
  11. Which state would you choose if you could live anywhere else?
  12. Which country would you want to live in if you had the opportunity?
  13. Do you prefer to ski, snowboard, or surf?
  14. How do you impress women by telling them about yourself?
  15. Which celebrity would be the worst to eat dinner with?
  16. Is there anything that makes you angrier than it needs to be?
  17. What flavor combination is unusual to you, but do you enjoy it?
  18. What do you consider to be your most prized possession?
  19. Is there something you never get tired of doing?
  20. Who is your favorite comedian? Which joke do you like the most?
  21. What show do you enjoy that would surprise people if they knew?
  22. Do you have anything about yourself that only your partner knows about?
  23. Would you rather use Instagram or Facebook if you had to choose?
  24. Is there anything about which you are aware that you are judgmental?
  25. What do you hate discussing at parties or get-togethers?
  26. If you could have ice cream every day, what flavor would you choose?
  27. What is anything that you believe should be legal but isn’t?
  28. When it comes to your daily routine, what is your favorite part?
  29. If you had to choose between giving up coffee and giving up alcohol, which would you choose?
  30. What is the most romantic film that comes to mind?
  31. What would be the finest gift a girlfriend could give you?
  32. So far, which age has been your favorite?
  33. What age were you when you had the happiest birthday of your life?
  34. Who was your first celebrity crush?
  35. What age were you when you first kissed?
  36. How do you know when you’ve fallen in love with a woman for the first time?
  37. What is the most practical skill you have ever gained?
  38. Can you think of something that happened to you that you wouldn’t believe if you weren’t there?
  39. What is one temptation that you can’t seem to avoid?
  40. What is your current least favorite fashion trend?
  41. Where do you like to shop the most?
  42. What was the most historic event you personally witnessed or participated in?

Really random questions to ask a guy

One of the biggest causes of guys losing their interest in a conversation is that they think that it’s all planned. Even if you have the best questions and all the charm, they won’t accept it. They don’t want to have those planned questions as it might bore them.

And what is better than throwing them in some really random questions? These questions are quick and also open up subjects to elaborate on later. This way you will find the most facts and let him get to know you at the same time.

  1. What’s one of your favorite funny stories to tell that always gets people laughing?
  2. What do you do before going to bed every night?
  3. Do you consider yourself more of a night owl or a morning person?
  4. Which decade would you choose to live in if you could travel back in time?
  5. What about your childhood do you miss the most?
  6. Which fictional character is your favorite? Do you still like him? 
  7. Would you prefer to see a comedy or an action/adventure film?
  8. Do you have a favorite festival? How would you most likely celebrate it? 
  9. What’s one thing you’re particularly good at in the kitchen?
  10. Is there anything you wish you were very excellent at in the kitchen?
  11. When you’re having a difficult day, what dish do you turn to for comfort?
  12. What are the signs that a woman is flirting with you?
  13. What has happened in your life that seemed like the worst thing at the time but turned out to be the best thing in the end?
  14. What does a healthy relationship mean to you?
  15. If you could tell your younger self one thing, what would it be?
  16. What makes you feel like a kid at all times?
  17. What would you give up if you had to give up one of your favorite foods?
  18. If you were a ghost, who would you choose to haunt? Do you believe in ghosts?
  19. What is one thing you would do if you were president of the United States?
  20. When you’re on vacation, what’s your favorite activity to do?
  21. On vacation, would you rather relax or explore and go on adventures?
  22. If you had to choose between giving up meat and giving up sugar, which would you choose?
  23. If you had to choose between cake and cookies, which one would you choose?
  24. What do you believe to be the worst aspect of the internet?
  25. What is one activity you wish you had time to do every morning but never do?
  26. Who do you consider to be the most significant person in your life?
  27. Which film do you hate but which everyone else appears to enjoy?
  28. What do you enjoy even if you’re too old for it?
  29. What did you enjoy doing once but won’t do again?
  30. Tell me about the most meaningful gift you’ve ever received.
  31. What makes you feel sentimental all of the time?
  32. What is your preferred method of flirting with a woman?
  33. When was the last time a complete stranger did you a favor?
  34. What’s a horror movie that you enjoy despite knowing it’s bad?
  35. What makes you happy even when everything is going wrong?
  36. What would you do if your partner cheated you?
  37. Have you ever hurt someone’s feelings? Or do you regret it after hurting someone’s feelings? 
  38. How do you deal with people you don’t particularly like?
  39. What is something you’ve wanted to do for a long time but haven’t yet done?
  40. What is the most funny film you’ve ever seen?
  41. Do you prefer Halloween or Christmas?
  42. How do you think a good person is defined?
  43. Have you ever had a drug or alcohol addiction?
  44. What do you think the reason for the high divorce rate is?
  45. Do you have any advice for friends who are going through a breakup?
  46. Would you rather be late or early all of the time?
  47. What animal do you fear the most? And why?
  48. What is one personality feature in a lady that you value the most?
  49. What is one personality feature that you truly hate in a lady?
  50. Which city is your favorite so far? Have you ever visited there? 
  51. Where do you like to buy takeout the most?
  52. Do you prefer to travel with your friends or with your significant other?

Good random questions to ask a guy

Like any other person, guys also share their true opinions once they trust the person. They may not do so right away but gradually it happens. 

As you listen to them they will free up to tell you anything. Everything is possible with patience, time, and a relaxing environment. Here is the list of good questions to ask a guy for great conversation starters. 

  1. If you had to donate to one charity, what would it be?
  2. If you were to make a movie about your life, who would you like to play your life role?
  3. In a film about your life, who would you choose to play your love interest?
  4. What do you consider to be the most difficult aspect of working every day?
  5. Do you have any regrets till now? 
  6. Do you think it’s possible to fall in love at first sight?
  7. Is there anything about your family that you wish you could change?
  8. What is the strangest dream you’ve recently had? When did you plan to fulfill it? 
  9. Can you tell me about the worst lie you’ve ever told a girlfriend?
  10. Do you know how to identify if someone is lying to you?
  11. Do you believe that everyone has a single soulmate or that everyone has several soulmates?
  12. Would you rather have the power to see through walls or the ability to read people’s minds?
  13. What is your most appreciated feature?
  14. Would you prefer to spend a Saturday night out with your friends or with a woman?
  15. What is your most valued childhood possession?
  16. Is there anything about you that you hope your mum never finds out about?
  17. What is the strangest thing you’ve recently seen in the news?
  18. Where have you ever kissed someone in the weirdest place?
  19. When you’re bored, what do you daydream about?
  20. What did you take for granted in your previous relationship?
  21. Has anyone ever caught you naked in your house?
  22. If you didn’t know me, how would you describe me to someone who didn’t know me?
  23. What is a favorite family memory of yours? Can you tell me about this? 
  24. What is one of your favorite traditions?
  25. Which reality show is your favorite? And why? 
  26. Who is your favorite Kardashian or Jenner?
  27. Would you rather be a model or an actor if you had to choose?
  28. Before you tried it, what did you think was silly?
  29. Would you like to arrive at work early and leave early, or arrive late and leave late?

Cute random questions to ask a guy

Everyone loves cuteness! Even guys love to talk about cute things. To grab his attention and get to know him better along with creating a cute and funny environment, here are some cute random questions to ask a guy for good conversation. 

This way you will build a strong bond and come to know about him deeply. 

  1. I’d like to know more about your hometown. What is something unique about it? 
  2. What’s it like to be a part of your family?
  3. Do you have a nickname? If you do, can you tell me how you got it? Is it to your liking?
  4. What would you say is the difference between your present town and your hometown? Which one is your favourite? 
  5. How has your town changed over time, if he still lives there?
  6. Are you happy with your current position? What is your ideal job? What would you change if you had your dream job?
  7. What can you tell me about your friends? In a friendship, what do you value the most?
  8. What do you look for in a film? Which movie is your current favorite? 
  9. What is your preferred method of visiting a foreign country? Camping or hotels that are expensive?
  10. Who would play the lead role in your life if it were a movie, and why?
  11. What kind of pet-owning experience do you have?
  12. What three items would you bring to a desert island if you only had three?
  13. How do you feel about social media? How long do you think you’d be able to go without it?
  14. What are your key requirements when purchasing a phone? Brand, specifications, look, and personal recommendations?
  15. Have you ever had a paranormal experience? Do you know for sure if they’re real or not?
  16. What famous person would you wish to meet and why? Do they deserve to be admired?
  17. Do you believe that reality show participants have self-respect?
  18. What is your definition of karma? Have you ever come up with it? 
  19. How can you deny the existence of a higher power without concrete evidence?
  20. What are your thoughts on police brutality? What do you want to convey? 
  21. What would be the one meal that you could eat for the rest of your life?
  22. Even if you had a million dollars, what dinner would you refuse to eat?
  23. What would you do if you won $10 million in the lottery?
  24. Which era of history would you choose to live in if you could only live in one?
  25. With which world leader would you like to drink tea?
  26. Which of the ghosts would be the most fun to hang out with?

Random deep questions to ask a guy

The thought provoking, tacky, tricky and the strange conversation is the fuel of every relationship. These questions and subjects can make you take the guy’s hands and bring you into a challenging area. 

When you think you both have the same thought process then it’s the time to accept that whether you have or not. The deeper the question, the deeper the discussion will be. It’s about debates, opinions, different views and fun, knowledge at the same time.

  1. Do you want to risk the burning depths of hell with me by purchasing that chocolate cake? 
  2. Would you like to dig a little deeper into my meal with me? 
  3. Is everything fair in love and war? What’s to stop you? What’s the difference between the two?
  4. Will you be enticed to sink your teeth into my dessert?
  5. Do you want to exchange one Italian kiss, or a few? Can I trust you with a dirty little secret? (It’s the name of a well-known chocolate ice cream, but the name is a boon in one’s imagination, guys are attracted by mystery and intrigue). 
  6. Would you like to see my home, just in case?
  7. Do you want to join me on an adventure? Let’s assume you enjoy rock climbing and sailing. What do you think of that?
  8. What area of your body do you consider to be your favorite?
  9. When it comes to the female body, what type of look do you prefer?
  10. I’m sorry for staring at you so closely, it’s not that you’re very attractive. Can you forgive me?
  11. Do you believe you can keep your gaze on me for longer than I can?
  12. Is it just a chance that your shirt looks so beautiful on you, or did you get it custom-fitted?
  13. Do you believe this lighting is suitable for us?
  14. What would you think if we changed our location to something more intimate?
  15. Would you have another drink in an ideal world?
  16. How much does it take to make you a little tipsy?
  17. Isn’t it strange that Adam and Eve were brother and sister?
  18. What do you think the social implications of pornography are?
  19. What do you think the future holds for our culture?
  20. Do you believe that OnlyFans is beneficial to our society and culture?
  21. Do you pray to God on a regular basis?
  22. Who do you imagine you’re talking to when you consider who God is?
  23. Is it okay to use the term “maybe” in our daily lives? Or is it just “yes” and “no”?
  24. What would you ask God if you could ask him anything about life?
  25. What would you say if a fortune teller had to tell you the solutions to the universe’s questions?
  26. What aspect of your self-image would you change if you had to?
  27. Do you consider yourself to be a confident or secure individual?
  28. What are your own life aims? What is your plan for accomplishing it? 
  29. What is one item on your bucket list that you must complete before you die?
  30. Who was the last person with whom you had a relationship, and why did it not work out?
  31. Is it helpful to our culture and society to define religion?
  32. When you have a problem or an issue, who is the first person you turn to?

Random interesting questions to ask a guy

When it’s time to have some fun, interesting questions are right there for you! You know about many aspects of his life and get to know what kind of person he is in real life. This is really valuable material and you can relax now. The first step is always harder, so you can do it easily once you pass that phase.

Everyone loves challenging questions and men too. These interesting random questions to ask a guy will be playful and thought provoking as well for a conversation starter. As the conversation topic gets more interesting, he will get more close to you. Let’s deep dive into these questions.  

  1. Do you believe in a life after death? What about the life that came before life?
  2. What are your thoughts on the death penalty?
  3. Is global warming a genuine concern? Is it possible that global warming is just a natural cycle of Mother Earth, as storms have been for centuries?
  4. Is it possible to buy happiness with money? What about the fact that being happy at work might lead to earning more money?
  5. Is it the people who take drugs that are the problem, or is it the drugs themselves?
  6. When do you expect euthanasia to be legalized? Are you in favor of it or opposed to it?
  7. What are your thoughts on abortion? Do men have an equal voice in whether or not to keep the child?
  8. Is work a goal in and of itself, or should it simply be a means to an ideal life?
  9. What method do you believe was used to construct the pyramids?
  10. Do you believe communism will succeed? Or do you think it will fail? 
  11. How do you feel about the Vietnam War? What are your thoughts on it? 
  12. Would you choose to die for your nation if you had the option?
  13. Would you give your life to someone you care about?
  14. Do you believe in the possibility of reincarnation?
  15. In what cases is it ethical to commit a crime?
  16. Is it appropriate to make drugs legal? If so, under what conditions? If not, why not?
  17. Do animals have the same rights that humans do?
  18. What do you believe will happen when the world ends?
  19. What do you have planned for the weekend? Do you like to spend weekends with your friends? 
  20. What would you do if you had the freedom to do anything this month?
  21. On weekends, do you participate in any sports with your friends?
  22. What are your plans for tonight’s movie or TV show?
  23. What kind of books would you pick up if you went to a bookstore?
  24. What magazine do you usually buy while waiting in line at the supermarket?
  25. What snack do you usually grab at the grocery store when you’re checking out?
  26. What’s your go-to nutritional snack?
  27. What is your favorite late-night healthy food snack?
  28. What do you think your friend’s life will be like in the next five years?
  29. Who do you suppose you’d send to prison if you only had one friend?
  30. Hockey or football, which do you prefer to watch?
  31. Will you be checking any sports games this weekend?
  32. What do you like to bet on the most? Do you succeed most of the time? 
  33. What game would you play if you had to play only one game in Las Vegas right now?
  34. In today’s culture, what is your biggest pet hate about women?
  35. What is the most wonderful phone case you’ve ever had?
  36. Who are the people with whom you have the most interesting conversations?
  37. What creatures do you believe we were in our previous lives?
  38. When you’re in danger, how do you know what to say?
  39. What is your ideal part-time job that pays very little?
  40. Do you know who has the worst luck in the world?

Random personal questions to ask a guy

The riskiest part is asking personal questions since you have to be careful while asking questions about sensitive topics. Such questions might end up with spelling disaster if you ask them very soon. 

Ensure to build a strong and healthy bond before this level of conversation. When you build trust then you can ask these questions while having random conversations. 

  1. Which place do you believe has the better interior design? Do you want to find out?
  2. After a hard night, how do you feel about a healthy breakfast?
  3. Isn’t this spot a little too public?
  4. Tell me about a fantasy that makes you tremble just thinking about it.
  5. Is it true that the taste of pleasure comes from a stranger’s lips?
  6. Would you like to join us on a cocktail binge to see where we end up?
  7. Let’s put those fears to the test. Here’s one of my fantasies. What are yours?
  8. What is the most exciting film you’ve ever seen? Do you want to watch it again?
  9. What is the most sensitive area of your body?
  10. Which part of my body do you believe is the most gentle?
  11. Isn’t it about time you used those sexy forearms?
  12. Do you have a map with you? Because I believe I became confused inside your eyes.
  13. What do you think about us skipping dinner and going somewhere else?
  14. Sorry, just looking at you gets me carried away. Do you forgive me for this? 
  15. Is it legal to gaze at you as often as I do?
  16. Which part of your body do you hate the most?
  17. I think you’ll enjoy this daydream. Do you really like it? 
  18. I like how you make everything else seem unnecessary, is that the case?
  19. Isn’t it never boring with you? Do you feel the same? 
  20. You’re like a walking source of dirty thoughts. Or don’t you think so? 

Random sex questions to ask a guy

Intimate relationship is all about responsibility. Before going down this path, it’s necessary to know about sexual questions that are already being asked by people. 

Be gentle and sense the moment if you are moving in an intimate direction. Relax and respect the limits, then ask these questions to a guy for having a deeper bond and relationship. 

  1. I can recommend an excellent, sexy film. Would you like to join me in watching one?
  2. I’ve been doing some study on striptease. Do you want to see how good I am?
  3. Have you ever attempted bondage? It seems interesting to me.
  4. Who turned up the air conditioning? It’s hot here.
  5. What are your thoughts about foreplay? What is your most fantastical fantasy?
  6. Are you aware of how stunning you appear in that hoodie/shirt/to me/at all times?
  7. We could use a blanket because it’s cold. Can we do so? 
  8. What’s one sexual experience you’d like to forget? And why so?
  9. What’s one sexual experience you’ll never forget?
  10. How did it go the first time? 
  11. Which aspects of making love do you believe you could improve?
  12. Have you ever broken out laughing while having sex?
  13. Is it more casual or passionate?
  14. Is it better to be rough or gentle?
  15. What is the craziest thought that has ever entered your mind?
  16. Do you prefer to be active or passive?
  17. It’s a sin that you’re not committing, but I suppose we have to do something about it. What do you think? 

Random stupid questions to ask a guy

Relationships are not fake, they are breathing entities. If we got to view them closer, you can acknowledge the most embarrassing moments. They are an essential part of every person’s past, present and future. 

This series of questions is a barrier-breaker in that sense. You should try them to lighten the environment once you have grown close to one another. Here are the relevant stupid questions to ask a guy. 

  1. What’s your worst fast food experience so far? Do you regret eating that? 
  2. When you play a game, what game do you dominate?
  3. What movie scene has left you scarred for life?
  4. Which of your computer’s files is the most important?
  5. What is the most well-known feature of your hometown?
  6. What is the state of dating in the future?
  7. Aside from money, what do you never have enough of?
  8. What are some things you’ve done that you’d try to prevent others from doing?
  9. When was the last time you stayed awake for a long period of time?
  10. What is the most amazing funeral you can think of?
  11. How frequently does your mind go on autopilot?
  12. Which fact do you wish you hadn’t known?
  13. What is the one board game that always ends badly?
  14. When did the saying “looks can be deceptive” become truly meaningful?
  15. What childhood landmark was destroyed, and what was built in its place?
  16. What would you do if you awoke tomorrow in a 13-year-old body with all of your existing memories and experiences?
  17. What is the most valuable lesson your mother or father has given to you?
  18. What childhood pastime has been entirely ruined for today’s children?
  19. What modern technology do you hope to see in your lifetime?
  20. What old-fashioned method of doing things is better than the current method? Do you prefer doing that? 
  21. What are some things you haven’t seen or read and are well in due to popular culture?
  22. What is the most boring activity you can think of? And why? 

Random weird questions to ask a guy

Awkwardness never has the same importance. In the beginning, it’s more of a weird atmosphere. If you go too fast, he’ll possibly panic out and abandon ship. It plays the role of a bonding agent significantly, of course. 

Because of having awkward moments together, you will feel closer to each other. Here are some weird questions you can ask a guy. 

  1. What movie’s plot changes completely when one letter in the title is changed? What is the new movie’s plot?
  2. What two animals would you choose if you could morph them into one super animal? Why?
  3. Which animal would you choose if you had to pick one to help you win a fight?
  4. What are three grocery store items you could buy together to make the cashier laugh?
  5. Have you ever tried to set something on fire while cooking?
  6. What’s the funniest name you’ve ever heard someone use in real life?
  7. What would be your first step if a zombie apocalypse happens?
  8. Where would no one expect the bodies to be found?

Dirty random questions to quip to a guy

If you are not a faint-hearted person, then this is for you. When you are a girl, you have to do everything in that manner. This can include dirty talk too. Make him understand what you want to ask and what you mean but remember to be subtle. 

You both have trust in each other then it’s the time to move but with caution. Have the conversation in limit and be a little bit shy while asking. 

It’s worth noting that dirty questions to ask a guy can be used as a weapon on later dates. If you both are close enough then ask these questions so that it won’t lead to any misunderstanding. 

  1. Where do you like to get massaged the most?
  2. What is your favorite sexual movie scene?
  3. Are there any fantasies you have?
  4. Have you had a one-night stand before?
  5. What’s the strangest location you’ve ever done it in?
  6. Do you enjoy it when your hair is pulled?
  7. What is the most naughty place you’ve done it?
  8. Do you have more romantic feelings in the morning or evening?
  9. In bed, what do you do best at?
  10. Have you ever done it in the open air?
  11. What is the most memorable bedroom encounter you’ve ever had?
  12. What are your thoughts on dirty talk?
  13. Is there anything in your bedroom that turns you off?
  14. What is the longest time you haven’t done it?
  15. What’s the most straight time you’ve done it?
  16. What’s one public location you’d like to do it in?
  17. Have you ever had a kind friend?
  18. What would you do to me if I were in your room right now?
  19. Which sex position is your favorite?
  20. What’s the sexiest thing you’ve ever heard in bed?
  21. When do you feel most excited?
  22. What is the most filthy fantasy you’ve ever had?
  23. How do you feel about foreplay?
  24. What are your thoughts on friends with advantages?
  25. Do you prefer your intercourse with the lights on or off?

Random flirty questions to ask a guy

Opening up the conversation and challenging someone for the first attempt of everything. If you like to do what you hear, then you can move to the sensitive subjects and try to get him in. flirting is the key to all fun. 

Just be yourself and relax. Here is the desired list of questions to ask a guy. 

  1. What’s your favorite place for a drink? Do you want to visit there with me? 
  2. Would you rather have a long walk and talk on a date or go out on the town?
  3. Do you enjoy talking on the phone or sending text messages all day?
  4. What is something that all guys should do for their girlfriends?
  5. Who would you want to look like if you could appear like any celebrity, and why?
  6. Do you think men and women should have separate roles in the home?
  7. What has been the worst date you’ve ever had? And why? 
  8. What is the most bizarre thing you’ve ever done with a loved one?
  9. On our second date, what strange activity would you like us to do?
  10. What’s the worst thing you’ve ever done with a female in a relationship?
  11. On weekends, what is your favorite game to play?
  12. Which would you prefer: a kiss on the neck or a kiss on the hand?
  13. What is it about your crush that really turns you on?
  14. How would you spend all of the money in the world if you had it?
  15. What is one thing you aren’t proud of from a previous relationship?
  16. What’s the funniest date thing you’ve ever done?

Travel questions to ask a guy

A guy who loves to travel will also love to talk about traveling and related things. You will also come to know his interest in traveling. If you are a travel person then this is great to go ahead and ask these travel questions. 

Here is the complete list of random travel questions to ask a guy during conversations. 

  1. Would you like to say that you are an adventurer?
  2. Do you personally want to explore more or just be a homebody?
  3. Do you like to expire locally or go on an overseas trip? What will you choose?
  4. Could you be with a girl who didn’t want to travel much?
  5. If we get a chance to time travel then to what age or era would we go?
  6. Would you like to travel to another country? If so, then which country? 
  7. Which country is at the top of your bucket list to visit and why do you like to visit there?
  8. Would you rather like to travel to another country or live there for love?
  9. If you get your dream job in another country, would you go there or just stay here?
  10. Which country would you like to choose between India and China?
  11. What is your bad habit while traveling? Do you want to improve it or just ok with it?

Random food questions to ask a guy

We humans love to eat whether one is foodie or not. If a guy loves to eat then he would also love to explore more foods and talk about the random food stuff. 

If you want to get deeper into the food part and want to know his interest level, then it is a good idea to start with the relevant list of random questions below. 

  1. Which is one of the foods that you can’t live without?
  2. Is there any food that you would give up for a relationship?
  3. Which one food do you don’t like to eat and why?
  4. Do you like whipped cream? If so, then why?
  5. Would you like to be into body paint?
  6. Would you consider yourself a foodie or not?
  7. What would you feel if a girl is more foodie than you?
  8. If you could eat only food for the rest of your life then which one would you like to eat?
  9. Do you believe in the effects of aphrodisiacs?
  10. What would be your green mile meal?
  11. Are you a vegetarian or a non-vegetarian?

Random entertainment questions for a guy

Entertainment is an important aspect of life. If your entertainment preferences don’t align then might end up before it has to begin. Therefore, it’s the right time to develop an interest in entertainment and get involved and enjoy the process. 

In this matter, here are some random questions which you can ask a guy to know his interest. 

  1. What is your most favorite way to relax after a tiring day?
  2. Do you like to watch Netflix? If so, would you like to join me?
  3. Do you prefer bars or clubs for having fun?
  4. Do you prefer to exercise at a gym or at home?
  5. Do you prefer to watch television alone or with a partner?
  6. What type of music do you like to listen to most? 
  7. What song would you like to dance to at your own wedding?
  8. Who is your female celebrity crush and from how much time?
  9. What do you think is the most handsome and hottest male celebrity?
  10. Would you dump your girlfriend for a date with your famous crush?

Random life questions to ask

Being practical about life is so important. And it becomes even more important when it comes to a guy. Therefore, if you are looking forward to your relationship then it’s necessary to know his thoughts about life and wellbeing. 

Here is the complete list of random questions about life to ask a guy to keep conversation flowing. 

  1. Do you ever think that you would become a baby daddy?
  2. How many kids do you see yourself having in future?
  3. What do you think your family and friends would say about me if they met me for the first time?
  4. Tell me something that I don’t know about life till now. 
  5. What are the 3 most important things on your bucket list this year?
  6. What is the most memorable moment that you never want to forget?
  7. Have you ever thought of an age you would love to marry before?
  8. What is the real meaning of marriage for you? 
  9. Could you marry someone outside your faith?
  10. What is your most favorite memory till now?
  11. Where do you see your life in the next 5 years?
  12. What has been the most terrible incident that has ever happened to you?
  13. What can be a one solution for world problems?
  14. If you win a lot of dollars in a lottery then what would you do with that money?
  15. If you had to choose one person to train with, who would it be?
  16. Do you think you could go to the Victoria’s Secret website and pick two items of lingerie that you’d like to see on a woman like me?
  17. What would you say to your President if you happened to run into him on the street?
  18. If you were given the opportunity to travel anywhere on the planet, where would you take me?
  19. Can you think of a title for a movie that best describes your current situation?
  20. How long have you known your best friend and who is he/she?
  21. Who would you choose for lunch if you could have lunch with anyone, living or dead?
  22. What do you believe is the world’s most challenging issue right now?
  23. What do you want to do in your life for people or your country before dying?
  24. Would you rather ask permission and risk being denied, or would you rather ask forgiveness later?
  25. What do you think others will think of you? What do you think are the nicest things and worst-case?

Wrapping up

Speaking to who you like can be a daunting task. It can only be daunting if we think about it that way. We become nervous because we are afraid of failing. But it doesn’t have to resist anymore. Nothing can go as you plan but that’s just the beauty of conversation to your dream guy.

Have courage and don’t be afraid to show him that you care and want to know him better. Start with a simple question like “How was your day”. Such a move will save the conversation. You might end up having him for the rest of your life. Just go ahead and explore his thoughts and ideas!