400 Questions to Ask a Guy

Whether you’re on a first date, catching up with a friend, or trying to deepen your connection with someone special, having a set of thoughtful questions at the ready can be your compass. 

Asking the right questions not only breaks the ice but also opens doors to understanding his perspectives, experiences, and what makes him tick. 

To Get to Know Him

  1. What’s one thing you’ve always wanted to try but haven’t yet?
  2. Which book has impacted your life the most?
  3. What does your perfect weekend look like?
  4. Who has been the most influential person in your life?
  5. What’s your earliest memory?
  6. How do you like to spend your free time?
  7. What are you passionate about?
  8. What would you do if you won the lottery tomorrow?
  9. What’s one place you’ve always wanted to visit?
  10. What’s something you’re proud of?
  11. What type of music are you into?
  12. What was your favorite subject in school?
  13. What’s one hobby you’d like to pick up?
  14. Have you ever volunteered? If so, where?
  15. What’s the most adventurous thing you’ve done?
  16. Where did you grow up, and what was it like?
  17. What’s your dream job?
  18. Do you have any pets? What are their names?
  19. What’s something you wish people knew about you?
  20. If you could have a superpower, what would it be?
  21. Who is your favorite author or filmmaker?
  22. What’s your favorite meal to cook or eat?
  23. What are you currently watching on Netflix or any streaming platform?
  24. What’s something you’re looking forward to?
  25. What’s your fondest childhood memory?
  26. Do you prefer cities or nature?
  27. What’s something you’ve learned about yourself last year?
  28. If you could meet anyone, living or dead, who would it be?
  29. What’s something you’re a bit embarrassed to admit you like?
  30. Do you have any hidden talents?
  31. What’s one thing on your bucket list?
  32. Do you have any siblings? Tell me about them.
  33. What’s your favorite way to unwind after a long day?
  34. What are you most thankful for?
  35. Do you believe in fate?
  36. What’s your favorite holiday, and how do you celebrate it?
  37. Have you ever had a nickname? What’s the story behind it?
  38. What would you say are your best qualities?
  39. What’s something new you’ve tried this year?
  40. How do you handle stress or pressure?

About Relationships

  1. How long was your longest relationship?
  2. What do you think is the most romantic thing you’ve done?
  3. Do you think it’s okay to keep secrets in a relationship?
  4. How do you feel about public proposals?
  5. What’s your idea of the perfect honeymoon?
  6. How do you know when you’re in love?
  7. Do you believe in staying friends with an ex?
  8. What’s the biggest relationship mistake you think people make?
  9. What’s more important: physical attraction or emotional connection?
  10. Do you believe in “the one“?
  11. How important is it to meet your partner’s family?
  12. How would you handle disagreements in a relationship?
  13. Do you think a relationship can recover from cheating?
  14. What are your thoughts on age differences in a relationship?
  15. How do you feel about dating someone from a different cultural background?
  16. How would you feel about relocating for love?
  17. What’s your opinion on long-term relationships without marriage?
  18. Do you think it’s important for a couple to share hobbies?
  19. What’s your stance on dating apps and websites?
  20. How do you feel about lending money to your partner?
  21. Do you think opposites attract?
  22. What’s your view on dating someone with kids?
  23. How do you feel about spending holidays with a partner’s family?
  24. What’s your opinion on pet names for partners?
  25. How do you feel about sharing household responsibilities?
  26. Do you believe in relationship “rules“?
  27. What do you value the most in a relationship?
  28. What’s been your longest relationship, and what did you learn from it?
  29. What’s one thing that’s a deal-breaker for you in relationships?
  30. How important is trust to you in a relationship?
  31. How do you balance personal space with intimacy in a relationship?
  32. Would you relocate for love?
  33. What lessons have your past relationships taught you?
  34. How do you handle heartbreak?
  35. What’s your take on online dating?
  36. How do you define commitment?
  37. What’s something you’d never compromise on in a relationship?
  38. How do you handle jealousy?
  39. How do you maintain your identity within a relationship?
  40. What’s your view on financial management in relationships?

Over Text

  1. What’s been the highlight of your day so far?
  2. If you could teleport anywhere right now, where would you go?
  3. What’s the last photo you took on your phone?
  4. Got any silly fears or phobias?
  5. What’s your “go-to” emoji?
  6. What song is stuck in your head right now?
  7. Seen anything funny on the internet lately?
  8. What’s your comfort food on a bad day?
  9. If you were an animal, which one would you be?
  10. What’s something small that made you smile today?
  11. If you could have dinner with any fictional character, who would it be?
  12. What’s your favorite meme or GIF?
  13. What’s a fact about you that surprises people?
  14. How do you wind down before bed?
  15. Know any good dad jokes?
  16. What’s the most random thing you can think of right now?
  17. If your life was a movie, what would the title be?
  18. What’s your hidden talent?
  19. Do you have a favorite quote or saying?
  20. What’s your typical morning routine like?
  21. If you could learn any skill instantly, what would it be?
  22. What’s something you’re curious about lately?
  23. Have you ever had a nickname? What’s the story behind it?
  24. Are you a night owl or an early bird?
  25. What’s a topic you could talk about for hours?
  26. What’s the weirdest food you’ve ever tried?
  27. Do you believe in aliens?
  28. What’s a movie you can watch over and over without getting tired of it?
  29. What’s an app you can’t live without?
  30. What’s the best piece of advice you’ve ever received?
  31. If you could only listen to one song for the rest of your life, what would it be?
  32. What’s something you miss from your childhood?
  33. What’s the first thing you notice about someone when you meet?
  34. Do you prefer calls or texts?
  35. What’s a skill you wish you had?
  36. What’s the worst movie you’ve ever seen?
  37. If you could switch lives with anyone for a day, who would it be?
  38. What’s something you’re looking forward to this week?
  39. What’s your favorite way to spend a rainy day?
  40. Do you have any pet peeves?

Flirty Questions

  1. How do you manage to look so good all the time?
  2. What’s something you find really attractive that you think others don’t notice?
  3. Do you believe in love at first sight, or should I walk by again?
  4. What’s your idea of the perfect kiss?
  5. If we were on a deserted island, what’s the one thing you’d want to have with us?
  6. How do you feel about holding hands?
  7. What’s something that always makes you feel butterflies?
  8. What do you wear to bed?
  9. What’s the most romantic thing you’ve ever done?
  10. If you could describe my vibe in three words, what would they be?
  11. Do you like it when people make the first move?
  12. What’s something you’ve always wanted to say to me but haven’t?
  13. How would you impress someone you’re interested in?
  14. What’s a deal-breaker for you in a relationship?
  15. Do you prefer cuddling or making out?
  16. How do you know when you’re really into someone?
  17. What’s your secret talent that you think I should know about?
  18. If we could go on any date you wanted, what would it look like?
  19. What makes you feel connected to someone?
  20. Do you think you’re a good kisser?
  21. What’s something risky you’ve always wanted to try in a relationship?
  22. How do you express your affection?
  23. What’s your idea of a perfect day spent together?
  24. If you could have any celebrity crush join us right now, who would it be?
  25. What’s the most flirty thing you’ve ever done?
  26. How do you feel about public displays of affection?
  27. What’s one thing you’ve always been curious about in a relationship but never tried?
  28. What’s the sweetest thing you’ve ever done for someone you were interested in?
  29. Do you like surprises in a relationship?
  30. What’s the best compliment you’ve ever received?
  31. What’s something about you that you think I’d find irresistibly attractive?
  32. If we were in a movie together, what kind of movie would it be?
  33. What’s your favorite thing about someone you’re attracted to?
  34. How would you describe the perfect relationship?
  35. What’s the most important thing in a relationship for you?
  36. If you could plan the perfect date for us, what would it include?
  37. Do you prefer slow dances or fast, wild dances?
  38. What’s a romantic fantasy of yours?
  39. How do you feel about adventures in romance?
  40. What’s the best way to win your heart?

Funny Questions

  1. If you could swap lives with a cartoon character for a day, who would it be and why?
  2. If animals could talk, which would be the rudest?
  3. What’s the worst possible name you could give a pet?
  4. In a zombie apocalypse, which household item would be your weapon of choice?
  5. If you were a villain in a movie, what would your evil plot be?
  6. If you could only eat one food for the rest of your life, but it didn’t affect your health, what would you choose?
  7. If you were a wrestler, what would your entrance theme song be?
  8. Would you rather fight one horse-sized duck or a hundred duck-sized horses?
  9. What’s the silliest reason you’ve ever gotten into a fight with someone?
  10. What’s the most useless talent you have?
  11. If you were a kitchen appliance, which one would you be and why?
  12. If you could have any mythical creature as a pet, what would it be?
  13. What’s the funniest joke you know by heart?
  14. If you could be a fly on the wall for any historical event, which would you choose?
  15. If you had to wear a t-shirt with one word on it for a year, what word would you choose?
  16. What’s something you’re really bad at but love doing anyway?
  17. If you could instantly become an expert in something, what would it be?
  18. What’s the weirdest conversation you’ve overheard?
  19. If you could live in any video game world, which would you choose?
  20. If you were a fruit, what fruit would you be and why?
  21. What’s the most ridiculous invention that you can come up with?
  22. If you had a time machine, would you go to the past or the future? Why?
  23. What do you think would be the worst “buy one get one free” sale of all time?
  24. If your life was a movie, which actor would play you?
  25. Would you rather have fingers as long as your legs or legs as long as your fingers?
  26. What’s the most embarrassing thing you’ve ever worn?
  27. If you were a superhero, what powers would you have?
  28. What’s the weirdest thing you’ve ever eaten on a dare?
  29. If you could only listen to one song forever, what would it be?
  30. If you found out you were the direct descendant of a king or queen, what would be your first royal decree?
  31. What’s the funniest word in the English language?
  32. How would you rate your karaoke skills on a scale of 1 to Mariah Carey?
  33. If you could morph two animals to make one super animal, what two animals would you choose? Why?
  34. What’s the most ridiculous fact you know?
  35. If you had a boat, what would you name it?
  36. Would you rather have unlimited sushi for life or unlimited tacos for life?
  37. What would be the coolest animal to scale up to the size of a horse?
  38. If peanut butter wasn’t called peanut butter, what would it be called?
  39. If you could choose what to come back as in your next life, what would it be?
  40. What would you do if you were invisible for a day?

Random Questions

  1. If you could instantly become an expert in any skill, what would it be?
  2. What’s the most unusual place you’ve ever visited?
  3. If you could have any animal as a pet, regardless of its size or nature, what would it be?
  4. If you could bring one fictional character to life, who would it be?
  5. What’s one thing you’ve always wanted to learn but never had the time for?
  6. If you could witness any event past, present, or future, what would it be?
  7. What’s the strangest food combination you’ve ever tried and liked?
  8. What’s one rule you live by?
  9. If you could have dinner with any historical figure, who would you choose?
  10. If you were a type of jeans, what type would you be?
  11. If you found a magic lantern and a genie gave you three wishes, what would you wish for?
  12. What’s the most random thing you can think of right now?
  13. If you could be any age for a week, what age would you be?
  14. What’s the weirdest dream you’ve ever had?
  15. If you were a superhero, what would your arch-nemesis be like?
  16. What do you think cats dream about?
  17. If you had to eat one meal every day for the rest of your life, what would it be?
  18. If you could instantly master any instrument, what would it be?
  19. What’s the best piece of advice someone has ever given you?
  20. If you were a character in any book, who would you be?
  21. Do you believe in ghosts? Why or why not?
  22. If you could have a lifetime supply of anything, what would it be?
  23. What’s the most interesting thing you can see out of your nearest window right now?
  24. If you could switch lives with anyone for a day, who would it be?
  25. What’s the funniest way you have ever been injured?
  26. If you could live in any TV show, which would it be?
  27. If you could change one thing about the world, what would it be?
  28. What’s the best wrong number call or text you’ve ever received?
  29. If you were an ice cream flavor, what would you be and why?
  30. What’s something that everyone looks stupid doing?
  31. If you could have one song play every time you entered a room, what would it be?
  32. What’s the most useless superpower you can come up with?
  33. If you were a vegetable, which would you be and why?
  34. What’s the silliest reason you’ve ever been late?
  35. If you could only use one word to describe yourself, what would it be?
  36. What’s the most bizarre thing you’ve ever found in your food?
  37. If you could spend a day in someone else’s shoes, whose would they be and why?
  38. What’s something that’s legal but feels illegal when you do it?
  39. If you could instantly teleport, where is the first place you’d go?
  40. If you were a pizza topping, what would you be?

Personal Questions

  1. What has been the most significant decision of your life so far?
  2. What are you most passionate about?
  3. What’s one thing you’ve done that you’re most proud of?
  4. What is the hardest lesson you’ve had to learn?
  5. How do you define success?
  6. What’s a personal habit that you think has contributed the most to your success?
  7. What’s the biggest risk you’ve ever taken?
  8. What has been your biggest mistake, and what did you learn from it?
  9. What’s one moment that fundamentally changed your life?
  10. What do you value most in friendship?
  11. What does your ideal life look like?
  12. What personal qualities do you think are most important?
  13. What’s one personal challenge you’ve overcome recently?
  14. What’s something about yourself you’re currently working on?
  15. How has your upbringing influenced who you are today?
  16. What are you most insecure about, and how do you deal with it?
  17. What’s one thing you wish more people knew about you?
  18. What’s the most important thing you look for in significant others?
  19. What’s something you’ve always wanted to do but have been too scared to try?
  20. What’s the most personal thing you’re willing to share with a stranger?
  21. How do you handle setbacks or failures?
  22. What’s one memory you’d love to relive?
  23. What’s something you’re surprisingly good at?
  24. What do you do to relax when you’re stressed?
  25. What’s one thing you’d like to change about yourself?
  26. What’s the best compliment you’ve ever received?
  27. What’s something you’ve learned about yourself during the pandemic?
  28. How do you handle criticism?
  29. What’s something that’s helped you grow as a person?
  30. What’s one skill or hobby you’ve always wanted to learn?
  31. What’s the kindest thing someone has ever done for you?
  32. What’s one thing you’re looking forward to in the future?
  33. What do you think is the meaning of life?
  34. How do you feel about the concept of destiny?
  35. What’s something you believe in that not everyone does?
  36. What have you done that’s outside of your comfort zone?
  37. What would your autobiography be titled?
  38. How do you define happiness?
  39. What’s your biggest fear, and how do you face it?
  40. What legacy do you hope to leave behind?

Interesting Questions

  1. If you could time travel, would you go to the past or the future? Why?
  2. What invention do you think will be popular in 20 years?
  3. If you could learn the truth behind any one secret or mystery, what would it be?
  4. What’s the most interesting fact you know?
  5. If you could live in any book, TV show, or movie world, where would you choose?
  6. How do you think technology will change everyday life in the next 10 years?
  7. If you could have a conversation with any person from history, who would it be?
  8. What’s one place on earth that feels magical or mystical to you?
  9. If you were given a one-minute ad slot during the Super Bowl, what would you fill it with?
  10. What’s the most bizarre dream you’ve ever had?
  11. If you could instantly become fluent in another language, which language would you choose?
  12. What’s an unpopular opinion you have about a popular show or movie?
  13. If aliens landed on Earth tomorrow and offered to take you home with them, would you go?
  14. Which historical figure do you think would adapt the fastest to today’s world?
  15. If you could witness any event in history, what would it be?
  16. What’s the biggest “what if” you often think about?
  17. If you could have any animal’s features, what animal’s features would you choose and why?
  18. What’s one mystery of the universe you’d love to solve?
  19. If you had a theme song that played every time you entered a room, what would it be?
  20. If you could ban one thing from this world, what would it be and why?
  21. What’s something that everyone should experience at least once in their lifetime?
  22. If you could give a TED talk on any topic, what would it be?
  23. What do you think the world will be like in 100 years?
  24. If you could start a charity, what would it be for?
  25. What do you think would be humanity’s reaction to the discovery of extraterrestrial life?
  26. What’s one thing you’d change about human nature?
  27. If you had the power to solve one world problem, what would it be?
  28. How would you spend a billion dollars in one week?
  29. If you could bring back any extinct animal, which would you choose?
  30. What’s a skill or talent you wish you had?
  31. What’s one question you’d ask a psychic about your future?
  32. If you were tasked with inventing a new sport, what would it be like?
  33. What’s something that’s considered a luxury but you don’t think you could live without?
  34. If you could eliminate one thing from your daily routine, what would it be?
  35. What’s an unusual fear you have?
  36. If you could relive one year of your life, which would it be and why?
  37. What’s one piece of technology from a movie you wish existed?
  38. If you could have lunch with any fictional character, who would it be?
  39. What’s the most interesting piece of art you’ve seen?
  40. If you had to choose a new name for yourself, what name would you pick?

Thought-Provoking Questions

  1. Do you think free will truly exist, or is everything predestined?
  2. What does it mean to live a good life?
  3. If happiness was the national currency, what kind of work would make you rich?
  4. How would you describe consciousness?
  5. What’s something that society deems as normal but you find strange?
  6. If you could know the absolute truth to one question, what question would you ask?
  7. In what ways do you think the human race will evolve next?
  8. Can justice exist without fairness?
  9. If you could give every child in the world one piece of advice, what would it be?
  10. What do you think is the most significant event in human history?
  11. Is it more important to do what you love or to love what you are doing?
  12. What’s something that people assume about you but is actually not true?
  13. If you could change one fundamental thing about society, what would it be?
  14. How does one find purpose in life?
  15. What’s the difference between living and existing?
  16. Do you think technology brings people closer together or farther apart?
  17. What are the qualities of a true leader?
  18. If you had the ability to read minds, would you use it?
  19. Is it better to be loved or respected?
  20. How would you define beauty?
  21. What’s something you believe is worth fighting for?
  22. Do you think the ends always justify the means?
  23. What’s the role of individual responsibility in societal issues?
  24. How do you measure success in life?
  25. What does freedom mean to you?
  26. If you could rewrite one event in your past, would you? Why or why not?
  27. What role does fate or luck play in one’s life?
  28. What would world peace require?
  29. How do you find the balance between personal desires and the needs of others?
  30. In what ways are you the same as your childhood self?
  31. Is true happiness achievable, or is it always just out of reach?
  32. What do you wish people cared more about?
  33. Do you think history is doomed to repeat itself, or can we learn from the past?
  34. What’s the most important question we should be asking ourselves?
  35. How does love change a person?
  36. What’s your view on the relationship between art and science?
  37. Does nature or nurture have a bigger impact on who we become?
  38. Is privacy more important than security?
  39. What does success truly mean to you?
  40. If you had one message to leave for future generations, what would it be?

Deep Questions

  1. What do you think happens after we die?
  2. Do you believe in a life beyond this one? Why or why not?
  3. How do you define the soul?
  4. What’s the most profound personal change you’ve ever experienced?
  5. What moments define your life so far?
  6. What do you think is humanity’s greatest flaw?
  7. What’s something you’ve struggled with your whole life?
  8. How do you cope with the idea of aging?
  9. Do you believe people are inherently good?
  10. What’s been your toughest moral decision?
  11. What does forgiveness mean to you?
  12. What role does suffering have in human development?
  13. Have you ever had a moment where you felt truly at peace?
  14. What do you think the purpose of pain is?
  15. What does it mean to be truly alive?
  16. In light of our finite existence, how do you find meaning in your days?
  17. What do you fear the most about the unknown?
  18. How do you define true love?
  19. Is there anything you would die for?
  20. What do you think makes us truly human?
  21. How important is the pursuit of truth to you?
  22. What do you wish you could understand better about the world?
  23. What’s your view on the concept of destiny and free will?
  24. How do you make peace with things you cannot change?
  25. What’s something you believe that most people don’t?
  26. How do you differentiate between living and merely existing?
  27. What’s a belief you once held strongly that you’ve since changed your mind about?
  28. What does it mean to you to lead a good life?
  29. How do you maintain hope in a world that often seems hopeless?
  30. What’s an experience that fundamentally changed how you view the world?
  31. How do you find solace in difficult times?
  32. What’s something you’ve given up on? Why?
  33. Do you believe in karma or that good/evil is rewarded/punished in some way?
  34. What do you think is at the core of human suffering?
  35. How do you balance your needs with the needs of others?
  36. What’s a dream you’ve let go of?
  37. How do you deal with your insecurities?
  38. What’s the most important life lesson you’ve learned?
  39. How do you define wisdom?
  40. What do you hope your legacy will be?

Frequently Asked Questions

How do I avoid making the conversation feel like an interrogation?

Balance is key. Ensure to share your own stories and answers to create a genuine exchange. Listen actively to his responses and let the conversation flow naturally.

Are there any signs that he’s enjoying the conversation?

Signs that he’s engaged include maintaining eye contact, active listening (nodding, reacting appropriately), and contributing his own stories or questions. A relaxed body language and genuine smiles are also positive indicators.

What if he’s shy and not very talkative at first?

Give him time to open up and feel comfortable. Focus on questions about topics he’s interested in, and be patient and encouraging. Sometimes, sharing a bit about yourself first can help ease the tension and make him more willing to open up.


Final Thoughts

Remember, the goal is not just to fill the silence but to forge a bond, to understand and be understood. So the next time you find yourself sitting across from a guy equipped with these questions, you’re not just making conversation; you’re making a connection.

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Bea is an editor and writer with a passion for literature and self-improvement. Her ability to combine these two interests enables her to write informative and thought-provoking articles that positively impact society. She enjoys reading stories and listening to music in her spare time.