200+ Questions to Ask a Guy – All the questions you need

200+ Questions to Ask a Guy - All the questions you need

Whether you met this guy at the Gym, Mall or Spa. There’s bound to be some issues in starting a conversation at first. Sometimes you’re not sure if the guy will find it interesting, awkward or irritating. So even If a question sounds interesting to you, there’s no guarantee that the opposite party will be equally interested.

Thankfully, we’ve found an excellent way for you to converse with any Guy through a series of questions outlined here. You never have to run out of idea in every situation. Whether at the Bar, Mall, on a date, anniversary or Office. However, we urge you not to jump into questions without building some connection. It’s better to keep the conversation at a natural pace before chipping in one or two questions

 Questions to Get a Guy’s attention

It’s already hard to approach your crush let alone get his attention amidst other eligible girls around. What you need to get his attention is to take advantage of every moment you’re opportune to have with him by asking interesting questions that separate you from other girls.

  1. Do I have the trait of your ideal woman?
  2. Can you stop making me blush whenever you talk?
  3. Would you like to drive me back to my place?
  4. What was your most prized possession while growing up?
  5. How many times do you remember crying for losing your toys?
  6. What was the craziest thing you did in college?
  7. Are you looking for the hottest girl in the room? Then you’ve found her!
  8. Do you know that I liked you the first time I saw you?
  9. Do you think true love exists? And have you found the one?
  10. Tell me one thing you like about me?
  11. Have you ever cried in the middle of a Movie?
  12. Can you sing? If yes! I would love to hear you sing
  13. Why did you leave your previous girlfriend?
  14. What’s that one thing that’s would bring a smile to your face no matter how angry you were?
  15. Which do you prefer – hone cooked or junk Foods?
  16. What’s that nickname of yours you hated with all your life?
  17. Have you ever being in a fight?
  18. Do you feel the same Butterflies running in your stomach whenever you look at me?
  19. How often do Girls compliment you for your looks?
  20. Do you have any pets?

 Funny questions to ask a Guy

Whether you’re on a date, having a special moment with your crush or find yourself in a long conversation with an acquaintance, it’s always better to ease the tension between you two by asking funny questions. These questions are designed to make him laugh and initiate an easy-going conversation between you two.

  1. Can you remember the funniest thing you ever said that made nobody laugh?
  2. What’s the most embarrassing situation you’ve ever been?
  3. What’s the most awkward piece of clothing you’ve ever worn?
  4. If you were a Girl, what would be your favorite nightwear?
  5. Batman or Superman, who would you meet to save your Lady?
  6. Have you ever been caught trying to steak a piece of meat from mama’s pot?
  7. Are you terrible at Cooking?
  8. What’s the most hilarious childhood memory you have?
  9. Can you remember the most embarrassing thing you did when you were a child?
  10. If you were a Waiter, what would you do to a customer for speaking rudely to you?
  11. If you were to choose one of the two: Lingerie or Stilettos, which would it be?
  12. What do you think you would look like with make-up on?
  13. Can you think of a Movie that cracked you up?
  14. What’s the funniest thing you’ve ever done with a friend?
  15. Who would you have lunch with if you had a chance to choose between Beyoncé, Jennifer Lopez or Nicki Minaj?
  16. What’s the most embarrassing thing you’ve ever worn to bed?
  17. What Superpower do you wish you had?
  18. Are there things you were told as a kid and looking back you can’t help but laugh at how stupid they sound?
  19. What’s the worst thing someone said about you that made you cry?
  20. What’s your ideal Honeymoon?

 Casual questions to get to know him better

You’ve been friends for ages, but you still don’t know much about him, here are few questions to get him to open up to you.

  1. What’s the one thing you wish you could make with your hand?
  2. If you could be trained by any athlete who would that be?
  3. What’s the best food you’ve ever had?
  4. If you could be a wrestler who would you be?
  5. If you could take the brain of one person with the highest amount you’ve ever spent in a day?
  6. Who’s the most boring superhero you can hardly stand for 5 minutes?
  7. What were you obsessed with when you were younger but now think is stupid?
  8. What’s the worst decision you’re ever made?
  9. Which would you do if you had a chance to be with your favorite celebrity for a week?
  10. Would you rather go a day without social media or never watch your favorite football team play?
  11. If Robin Hood and Captain America fought who would you rather prefer won?
  12. What would you love to do to make the world a better place?
  13. If you had to spend the rest of your life raising a Pet, which animal would that be?
  14. Who’s your favorite comedian, and why do you love his jokes?
  15. The worst show you’ve ever attended?
  16. What were the best and worst years of your life?
  17. What’s the best thing you’ve ever done to someone you hardly know?
  18. What was the experience that brought out the best version of you?
  19. Who’s that one person you want to be exactly like when you grow up?

 Flirty questions to ask a Guy

Turn up the heat between you both by asking him flirty questions.

  1. Have you ever had sex in a car?
  2. If I had chocolate all over my body, would you lick it off?
  3. Have you ever had a lap dance from a stripper?
  4. What do you think about me when you touch me down there?
  5. What kind of woman would you like to go on a date with?
  6. Can you tell me one secret you’ve never told anyone before?
  7. What’s the most shameful thing you’ve ever done to a woman during sex?
  8. What’s the one thing you think will make me Fall for you?
  9. What’s your idea of a perfect kiss?
  10. What does the perfect woman look like?
  11. What’s your favorite nightwear?
  12. What’s the best part you like to be kissed?
  13. Can you go for a month or two without sex?
  14. Do you find tattoos sexy?
  15. How will you seduce me to have sex with you?
  16. Have you ever thought about me while riding on another woman?
  17. Would you love to take off my bra and see what’s down there?
  18. Tell me what you do if you return from work to find me chained to your bed naked?
  19. How’s someone as hot as you still single?
  20. So are you a romantic lover or dirty talker?

 Questions to start an interesting conversation with a Guy

  1. What’s your weekend always like?
  2. Would you love to hang out with me?
  3. What were you really into when you were a kid?
  4. Which would you go for, a great car or house?
  5. Have you ever taken a bullet for anyone?
  6. What’s the worst habit you would love to change?
  7. Are you afraid of the dark?
  8. Where is the perfect place to go on a date?
  9. What’s the best Birthday gift you’ve ever received?
  10. What was the worst book you ever had to read?
  11. Are there any movies that bring a tear to your eye?
  12. What do you wish your phone could do right now?
  13. What’s your favorite Football League?
  14. Who’s your favorite soccer player, and what makes him special?
  15. What’s the worst food to eat at a restaurant?
  16. Do you prefer hitting the road alone or with friends?
  17. How many countries have you traveled to?
  18. What do you think the next big Technological discovery will be?
  19. What’s the best international food you’ve had at a Restaurant?
  20. The worst piece of clothing you will never be caught wearing?
  21. What’s the most expensive pair of shoes you’ve ever worn?

Personal Questions to Ask a Guy

Personal questions can mostly be difficult for guys to answer. It’s easy to cross the line, but these sets of questions give you a free pass into their inner world without intruding their privacy.

  1. What’s your own definition of a waste of money?
  2. If your relationship was taking a downturn, what would you do to save it?
  3. What are your biggest goals in life, and what have you done to achieve them?
  4. What’s the biggest lie you’ve ever told to save someone you love?
  5. What lesson have you learned the hard way?
  6. What’s the one thing that has kept you going during tough times?
  7. What would you not do for a Million Dollars?
  8. What’s your opinion about settling down with a career Woman?
  9. Do you think men should pay the bills all the time or the girls should step in where necessary?
  10. Who’s the most important person in your life right now outside your family?
  11. A job or your own Boss?
  12. Who’s that one person you’re comfortable discussing just anything with?
  13. The kind of people you can’t stand for a minute?
  14. What’s your most priced asset?
  15. What sins do you think are unforgivable?
  16. What event would you rather pay to escape than leaving through?
  17. Looking back, what’s the one thing you wish you never did?
  18. Would you rather lie to keep a relationship going or tell the person the truth and damn the consequences?
  19. What are some of your rules that bend for no one?
  20. Would you rather be hated for standing by the truth or loved for telling lies?
  21. Have you ever thought of what people will say at your funeral?
  22. What’s the one thing or person you can lay down your life for?

Questions to ask your Boyfriend on a Date-night

Date nights for couples could be boring especially if the relationship is getting old. You find yourself talking about work, repairs at home, family and that dream vacation you will never have. Rather than keeping the mood stale, here are few questions to ask each other.

  1. What did you think about me the first time we met?
  2. Was it love at first sight with me?
  3. What do you wish was better in our relationship?
  4. What time of the day do you love to get intimate?
  5. What’s the one thing you wish I could change about myself, but you’re too scared to tell me!
  6. What are the things about me make you certain I am the one for you?
  7. Do you think I would make a good Wife?
  8. What’s your favorite night with me?
  9. What are your secret fantasies about me?
  10. Do you ever wish I could be like one of your favorite celebrities?
  11. Have you ever rebelled against your parents?
  12. If you could go back in time, what’s the one thing you wish you never said?
  13. Were you the cool or bad boy in college?
  14. Which of my friends do you think is more fun?
  15. What’s the one thing you hope stays the same about our relationship?
  16. Who was your first crush?
  17. When did you have your first kiss?
  18. What do you think about having a joint account?
  19. Who do you think is more honest in a relationship: Guys or Girls?
  20. How many Kids would you love to have?

Questions to ask on a first date

If you’re going out for the first time with a guy you would love to start something with, a great way to discover his area of interest would be to ask questions. If he loves to spend and you prefer to invest, or you love to spend some time with your loved ones while he loves being on the road, that won’t go well. It’s always good to find out their likes and dislikes before building something together.

  1. What do you enjoy doing in your free time?
  2. If you were to choose between movies and football, which would it be?
  3. What TV series or Movies do you never get tired of re-watching?
  4. What are some ridiculous things you do behind closed doors!
  5. Do you love pets and have you ever had one?
  6. Who’s your favorite Author?
  7. What international dish do you like?
  8. What’s the most embarrassing thing that has ever happened to you?
  9. If you were a bird, which one would you be?
  10. What Country do you wish or never want to visit?
  11. What do you think about Paris?
  12. What TV shows do you watch when you were 10?
  13. If you could go back in time, what would you love to change about your life?
  14. If you were to start your own business, what business would that be!
  15. If you unexpectedly win $20,000 today, what would you do with it?
  16. What’s your idea of a “dream job”?
  17. Are you a morning person or night owl?
  18. What would a perfect vacation be like?
  19. What’s your definition of a Perfect Day?
  20. What’s your definition of a perfect Woman?
  21. Do you party?
  22. If you could be a woman in one day, what would you do?
  23. What’re Your Favorite Sports?

Dirty Questions to Ask a Guy

An essential part of every relationship, especially when you two are getting to know each other is to engage in naughty discussions. This might come at a time when you need to find out more about him, especially his sexual desires and what excite him even further.

  1. Do you prefer to have the lights on or off during sex?
  2. If we were to place a bet on it, what color of paint do you think I am wearing?
  3. Which part of your body do you like being touched more?
  4. If you had just one chance to touch or kiss me, would part would it be?
  5. Have you ever had a one night stand, and what did you think about the person?
  6. Do you prefer to go hard or gentle in the bedroom?
  7. Do you love to always be on top or won’t mind your girl taking control sometimes?
  8. Would you like to have a sex chat with me?
  9. What part of my body makes you go crazy?
  10. How many minutes does it take you to unhook a bra?
  11. Who was your best and worst kiss?
  12. Do you like to keep it quiet or loud during sex?
  13. Have you ever done a quickie?
  14. Which celebrity do you fantasize about having sex with?
  15. Are you into older women?
  16. If you could only touch me in one place, where would it be?
  17. What would you do if you find me all Naked on your bed?
  18. What is the best meal you would have a woman feed you after sex?
  19. Have you ever sent a Nude picture to anyone?
  20. Would you love being filmed while doing it?
  21. When was the first time you did it?
  22. What is the hottest outfit that would turn you on in one minute?
  23. Have you ever had it with a Virgin?

 Questions To Ask Your Crush

You might notice that you’re beginning to develop feelings for a guy at your workplace but don’t know much about him. Hence, you might want to ask him a series of questions to know if his interest aligns with yours. Also, there are times when asking him personal questions will put him off balance. Hence it’s better to conceal your intention by keeping it casual.

  1. Are you a Mama’s boy?
  2. How many siblings do you have and are you the first child?
  3. What’s your pet name at home?
  4. What’s your favorite Football team?
  5. What’s your Zodiac sign?
  6. Who’s your favorite actor and which of their movie do you never get tired of re-watching?
  7. Who’s your favorite musician, and why do you like him?
  8. What do you do during your free time?
  9. Which of your accomplishments are you most proud of?
  10. Where do you see yourself in the next five years?
  11. Have you ever fallen in love?
  12. If you had a chance to be a celebrity for a day, who would it be?
  13. What’s the one thing you regret never doing?
  14. If a genie grants you three wishes, what would they be?
  15. If you were to tour around five Countries for free, where would that be?
  16. Do you have any childhood friends?
  17. Which part of life do you wish never took place?
  18. Do you think it’s easy to forgive and forget?
  19. What part of your life has improved in the last five years?
  20. Who’s your number one motivator?
  21. Name three of your Role models?


Before asking a Guy any question, you have to keep things simple, especially if you’re meeting this person for the first time. For instance, it will be completely off to start asking a Guy you met for the first time dirty questions. Besides, you have to put the personality of the guy into consideration. Is he an extrovert or introvert? Calm or aggressive? These determine the kind of questions to ask.

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