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Conversation can be difficult. That being said, Asking the right questions can help break the ice and make things feel natural.

Let’s face it, in order to get to know a guy, you need to ask him personal questions. 

Not only is the simple act of asking questions a fun way to have a good conversation with someone new in your life, it’s also a way of figuring out if you enjoy talking to each other. After all, if you want to take things to the next level at some point in the future, exchanging good ideas or asking random things can be a great way to speed up the process. If it turns out that you don’t have much in common, it’s better to know early in the process, right?

So next time you feel the urge to connect with someone but aren’t sure where to start, take some inspiration from the list we’ve assembled below, and start asking some random questions! We’ve broken some of our ideas into sections, so scroll down and find the section most appropriate for you.

30 flirty questions to ask a guy 

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Not everyone likes to get flirty right off the bat, but you should try out these fun questions that deal with the subject of love, relationships, and other great conversation starters. 

From a lighthearted question about a first kiss with someone of the opposite sex to your biggest regret in love, or just a conversation about your first crush, get going and start asking! Just make sure you pay attention to the answers. 

  1. If you could build your dream girl, what would she look like, and what would her personality be?
  2. What song would start playing every time you thought about me?
  3. Have you ever fallen in love unexpectedly?
  4. What is one compliment you think I have yet to hear?
  5. You have $500 to plan a romantic picnic, what would it look like and what would you include?
  6. Do you believe in love at first sight?
  7. Do you believe in fate?
  8. If I could read your mind, what do you think I’d find out?
  9. If you could read my mind, what do you think you’d find out?
  10. If your best friend was here, what would they say about you to make me like you more?
  11. Be honest, do you like a girl who plays hard to get?
  12. How do you get ready for a date?
  13. Do you prefer when girls make the first move?
  14. When was the last time you said the three words “I love you” for the first time? 
  15. How do you know when you’re falling in love?
  16. What is the weirdest thing you’ve ever done to impress a girl?
  17. Be honest, does a girl’s size matter?
  18. If you leave a girl on read, does it mean you’re not interested?
  19. What emoji do you usually flirt with?
  20. How does a guy know when a girl is the one?
  21. Have you ever been heartbroken?
  22. How many posts do you like on a girl’s Instagram page to hint that you’re interested?
  23. Define a girl who is beautiful inside and out.
  24. What was your first impression of me?
  25. Have you ever kissed someone in the heat of the moment?
  26. How far would you go for the girl you loved?
  27. What accents do you find sexy?
  28. What is your ideal first date on a Saturday night?
  29. If you were a magician and had only one magic spell to cast on me, what would it be?
  30. Where should we go for our second date?

30 personal and deep questions to ask a guy: from the dream job to the life motto

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  1. What’s your earliest memory as a child? 
  2. What would be your dream job, and why? 
  3. Name three things you hope to see in your future. 
  4. What life advice would you give to your 13-year-old self?
  5. How are your relationships with your exes?
  6. Describe your happy place.
  7. What’s your most embarrassing moment that was a really big deal at the time, but doesn’t matter as much any more as an adult?
  8. What is your favorite memory from school?
  9. What is hard to do but you know is for the best?
  10. Who are you closest to in your family and why? What’s your favorite family memory?
  11. What is one mistake you’ve made but don’t regret?
  12. Are you the same person you were five years ago?
  13. What is the most painful experience you’ve gone through, and what did you learn from it?
  14. What has been the happiest moment in your life so far?
  15. Have you ever said something you regretted?
  16. Do you ever wish your life turned out differently, and if so, why?
  17. Why do you think your past relationships never worked out?
  18. Who is the most important person in your entire life right now?
  19. Who do you owe a lot to?
  20. Where do you find peace?
  21. Do you believe in loving yourself before loving someone else?
  22. Who have you lost touch with that you’d hope one day to reconnect again?
  23. Have you ever healed from a broken heart, and if so, how?
  24. How do you define a healthy relationship?
  25. What is your biggest insecurity?
  26. What social cause has a special place in your heart?
  27. Who have you lost that you’d want to spend one more day with?
  28. When was the last time things didn’t go as planned, and how did you handle it?
  29. Who is the one person you wouldn’t want to live without?
  30. What’s your life motto?

20 weird questions to ask a guy

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Unexpected conversations can be so much fun, and sometimes the unexpected can arise out of some super weird prompts. 

These questions to ask a guy might be a little weird at first, but what you find might be an amazing start to a conversation that goes in all directions. You should ask a guy something that taps into humor, his imagination, his nerdy side – whatever you want. There are no rules for this section! 

  1. What do you think another version of you is doing in a parallel universe?
  2. If you could only eat one food for the rest of your life, what would it be?
  3. If all planets in the solar system were inhabitable, which one would you live on?
  4. If you had to play one video game with an historical figure, what game would it be, and who would you play with?
  5. If you could raise any dead celebrity back from the afterlife, who would it be and why?
  6. Which forbidden place on earth would you visit just for fun?
  7. If you were to lose all of your body parts except for one, which one would you want to keep and why?
  8. Have you ever been traveling and gotten completely lost?
  9. Has any horror movie made you paranoid of everyday things in your life?
  10. If future advanced technology could make people immortal, would you volunteer as a test subject?
  11. If you had to plan the most extravagant funeral for yourself, what would it look like and what would be included?
  12. If you had a billion dollars but couldn’t buy things for yourself,  what would be the best way to spend money?
  13. How much money is too much – should there be a legal maximum wealth?
  14. What is the worst superpower to have?
  15. If it were up to you to design heaven, what would it look like?
  16. If you could control people’s minds, how would you change the world?
  17. What is something you wish was real but isn’t?
  18. What is the most unusual thought you’ve had?
  19. If you could make yourself a morning person, would you?
  20. If you were one of the Seven Wonders of the world, which one would you be and why?

18 even weirder questions to ask a guy

These questions to ask a guy range from reincarnation to artificial intelligence to underwater cities. But don’t forget, there is no limitation in the list of subjects of your questions to ask a guy. Let your mind wander, think of something random, and before you know it, you’ll be building your own list of questions to ask a guy. 

  1. What animal would you want to be reincarnated into?
  2. If you were a drug dealer, how many phones would you need minimum?
  3. If you were an AI for the rest of your life, what type would you be? 
  4. What is the worst way to die? 
  5. If you were a time traveler, what era would you constantly visit? 
  6. What body part would you change, if you could change one on yourself? 
  7. If you were a muffin, what kind of muffin would you be? 
  8. If you were a robot, what features would you include in yourself? 
  9. What is your greatest fear in a dark room? 
  10. What is the scariest sound in the world?
  11. How would you explain the future to someone from the past? 
  12. If underwater cities existed, which lost city would you want to visit and why? 
  13. If you were granted one wish that’s promised to come true tomorrow, what would it be? 
  14. If you had three wishes and you couldn’t ask for money or anything of value, what would you ask for? 
  15. What’s the best prank you ever pulled with your friends? 
  16. If you ended up on the front page of a newspaper, what would you want it to say? 
  17. What is the most childish thing you’ve ever done? 
  18. Which Disney princess would you ask on a date?

16 funny questions to ask a guy

Not everyone considers themselves super funny, but even the most straight-laced individuals have their funny moments when asked the right funny or interesting question. Feel free to let loose and get silly with some of these funny questions to ask a guy.

  1. What is the coolest nickname you’ve heard someone go by?
  2. What was the funniest thing you’ve seen someone do for a TikTok video or on social media?
  3. If you were invisible for a day, what pranks would you get away with?
  4. Of all your male close friends, who would you want to date if you were gay?
  5. What is one bad habit you see no problem in, but another person would?
  6. Which 90s boy band member do you think you’re the most like?
  7. What is the funniest thing you’ve worn for Halloween?
  8. What is the funniest dad joke?
  9. What’s the funniest name a celebrity has given their child?
  10. What pet peeves do you have that make you truly angry, and can ruin your day?
  11. What song would play during your most embarrassing moments?
  12. What past commercial jingle do you still know off by heart?
  13. If animals were all friendly, which one would you have as a pet?
  14. If you became a meme, what inside joke would you be the face of and why?
  15. What have most people done that you know you’d never do?
  16. Have you ever had a wardrobe malfunction in public?

21 questions to ask a guy: random ones for interesting answers

When thinking of questions to ask a guy, sometimes the rare ones are the questions that reveal the most about a person. Sometimes, coming up with questions to ask a guy involves the movies, but it could deal with anything; his favorite fictional character, what we would do with a million dollars that he had to spend in two hours or less. 

Sometimes random questions are best! There are so many examples of questions to ask a guy, and don’t forget, this list is just a jumping-off point. Ask literally anything you want!

  1. What is one thing you’d never rant about publicly?
  2. What topic could you talk about for hours?
  3. If you were given a $25,000 watch as a gift, would you keep it or sell it?
  4. What is one admirable quality a woman has no guy yet noticed?
  5. What lesson have you learned from your parents that you’ll pass along to your kids? 
  6. If your life were a movie, which celebrity would you want to play your love interest?
  7. Which TV series is your life most like?
  8. What’s the kindest thing you’ve seen someone do?
  9. What other country would you want to live in? 
  10. What’s the last thought you have before going to sleep?
  11. What song would you put on repeat forever?
  12. What restaurant dish do you wish you could cook at home?
  13. Which teen heartthrob did you think would age well but didn’t?
  14. What is the motivation behind your dreams and aspirations?
  15. What’s something you regret judging?
  16. What is one thing you wish people wouldn’t judge you on?
  17. What are you most looking forward to in the future? 
  18. Which field of work would you be in if no experience were required? 
  19. What is an unethical practice society continues to do that you wish would end?
  20. Which former celebrity couple do you still think are soulmates? 
  21. If you had $1 million dollars to build your dream home, what would it look like and what would be in it?

In conclusion

When you ask a guy questions like these, it lets him know of your interest in him. It should tell him that you want to get to know him on the inside and out. But when you ask a guy questions, don’t forget that the ones you choose to ask sometimes say a lot about you too. Don’t be nervous, pick the questions you’d like to answer as well, and then let that conversation flow – you’ve got this!

Be sure to check out our article on questions to ask your crush, and questions to ask your boyfriend or girlfriend.