257 Questions to Ask a Guy to Get to Know Him Better

questions to ask a guy

Knowing what to say on a date can be difficult. Not to mention, the fear of awkward silences can have you begging your brain for inspiration on what to say! The early stages of dating are also an opportunity to learn more about someone.

Asking the right questions can help your date go smoothly—or if not, at least reveal early on that this guy isn’t the right match for you. Imagine falling in love with someone and finding out they love (or hate, choose the right one for you) pineapple on pizza!

To help you out, here are over two hundred great questions to ask a guy while getting to know him.

Icebreaker questions to ask a guy

Picture the scene: you’ve sat down with your date and exchanged the slightly awkward “Hi, how are you?” and “Did you get here okay?” questions, and have just ordered your meal and drinks. What do you say to start a conversation with a guy?

You don’t want to go too serious at first, but you want to ask a question that lets him talk about himself for a while. These questions are light-hearted enough to break the ice. They can also reveal interesting information about the handsome guy sitting opposite you!

  1. What’s the most exciting thing that happened to you today?
  2. What TV show can’t you get enough of lately?
  3. If you were to get a tattoo right now, what would it be?
  4. Do you think pineapple belongs on pizza?
  5. I like your shirt. Where did you get it?
  6. Do you have a party trick?
  7. If you had the day off tomorrow, what would you do?
  8. What’s the last concert or show you went to, and did you enjoy it?
  9. What’s something about you that you think I’d be surprised by?
  10. If you could bring back any old fashion trend, which one would you choose?
  11. What was the first album you ever bought?
  12. What’s your favorite cocktail?
  13. What’s the worst job you’ve ever done?
  14. If you had to describe yourself in three words, what would they be?
  15. What item of clothing would be your biggest turn-off if a girl was wearing it on a date?
  16. What superpower would you choose to have?
  17. What are two truths and one lie about you?
  18. What’s the funniest pickup line that you know?
  19. What’s your opinion on the five-second rule?
  20. If you had to perform karaoke right now, what song would you sing?
  21. How long have you lived here?
  22. Which dating apps do you use?
  23. If you could invite any three people—living or dead—to a dinner party, who would you choose?
  24. What one thing would you want on a desert island?
  25. If you were a woman for a day, what would you do?

The essential questions to ask a guy

girl with cofee looking at you

Once the ice has been broken on a date, you probably want to know more about this guy on a personal level. The answers to these questions will probably give you a good overall idea of who he is as a person, and if the two of you are compatible with each other. These are some of the most essential questions to ask a guy in the first couple of dates.

  1. Do you have any pets? If not, do you want them?
  2. Are you more of a cat person or a dog person?
  3. Do you get on well with all of your family?
  4. Do you have any role models outside of your family?
  5. Do you have a best friend?
  6. How do you think your friends would describe you?
  7. What is your favorite place in the world?
  8. Where would you like to be in five years?
  9. Do you enjoy your current job?
  10. What is your dream job?
  11. Are you more motivated by career or relationships?
  12. Do you enjoy cooking?
  13. Do you prefer a night on the town or a quiet night in with takeout and a movie?
  14. Are you more interested in winning or taking part?
  15. Do you think you will have children in the future?
  16. Were you brought up in a religious household?
  17. Would you describe yourself as “spiritual”?
  18. Do you believe in astrology?
  19. How much of a priority is money in your life?
  20. Would you describe yourself as more left-wing or right-wing?
  21. Would you describe yourself as more pro-choice or pro-life?
  22. What is your opinion on feminism?
  23. If you won the lottery and never had to work again, how would you spend your time?
  24. What is your most irrational pet peeve about a person?
  25. How would you spend your ideal weekend?
  26. Would you ever like to travel the world?
  27. Do you like surprises?
  28. Do you prefer summer or winter?
  29. How do you spend a typical Friday night?
  30. Do you smoke, and what is your opinion on smoking?
  31. How often do you use social media?
  32. What are you looking for from dating?

Follow up questions to ask a guy

couple in lunapark

So you have learned the basic information about the guy, and you are curious to get to know him better. These follow up questions are great to use on a date. Some of them are light-hearted, and others are slightly more serious. Still, all of them provide you with plenty to discuss to keep the conversation flowing on your date and avoid the dreaded awkward silences!

  1. What important thing do you think most people get wrong?
  2. If you had to watch the same movie every day of your life, what would you choose?
  3. Would you rather watch a movie or read a book?
  4. What chance have you taken that really paid off?
  5. What’s the weirdest tradition your family has?
  6. What’s the worst date you’ve ever been on?
  7. Have you ever been to a protest?
  8. Do you consider yourself a good dancer?
  9. Do you play a musical instrument?
  10. What was your favorite subject at school?
  11. What are you looking forward to most in the future?
  12. What was the best day of your life so far?
  13. Are you more of a morning or evening person?
  14. What is your most hated food?
  15. What was your first impression of me?
  16. Would you rather be famous and hated, or known and loved by only a few people?
  17. What’s the most embarrassing story you have?
  18. What’s the best gift you have ever received?
  19. How do you relax after a long, hard day?
  20. Do you believe in ghosts?
  21. What skill would you love most to learn?
  22. Which decade do you think had the best styles and music?
  23. What song would you want to be played at your funeral?
  24. Would you rather be ridiculously handsome or extremely intelligent?
  25. Would you rather accept a million dollars or an extra year to live?
  26. What’s the craziest thing on your bucket list?
  27. Would you rather be stranded on a desert island for a year alone or with your worst enemy?
  28. What well-loved “classic” movie you can’t stand?
  29. Who do you think is the most overrated musical artist ever?
  30. If you were an animal, what animal would you be?
  31. Which hobby or fandom has the worst fanbase?
  32. What thing did you like before it was “cool”?
  33. Do you believe that aliens are out there?
  34. Have you ever collected anything unusual?
  35. When you were a kid, what did you want to be when you grew up?
  36. What would your dream house look like?
  37. What brands do you refuse to buy or support, and why?
  38. What is your favorite restaurant, and what is your favorite thing on the menu?
  39. What did you get up to last weekend?
  40. What’s the scariest thing you’ve ever done?
  41. What life experience do you think everyone should have at least once?
  42. What would be your ideal date, if money were no object?
  43. What’s your favorite quote from a book, movie, TV show, song, or poem?
  44. What actor do you think makes any film worth watching?
  45. What’s your favorite word?
  46. What was the most delicious thing you’ve ever eaten?
  47. How many pairs of shoes do you think a person needs?
  48. Did you enjoy going to school when you were a kid?
  49. What is your earliest childhood memory?
  50. What is your favorite memory of summertime?

Fun questions to ask on a date

fun questions to ask a guy on a date

Although getting to know a guy can be a bit stressful at the beginning, let’s not forget that dating is supposed to be fun! If you want to share a laugh, these fun questions can lead to some exciting and hilarious conversations.

  1. If you had to perform a drag act, what would your drag queen name be?
  2. If your life could be one movie, which one would you choose?
  3. Who would play you in a movie about your life?
  4. If you could change your name, what would you change it to?
  5. What is your favorite little-known website?
  6. What was your best “mic drop” moment?
  7. Which celebrity would make the worst President?
  8. What did you love when you were younger, but you now can’t stand?
  9. What famous person completely lost your respect?
  10. What comedian has made you laugh the hardest?
  11. Who was your first celebrity crush?
  12. What was your favorite kid’s TV show when you were growing up?
  13. What one question can you ask any person to find out the most you can about them?
  14. What thing have you done that was fun, but you would never do it again?
  15. What’s the best and worst thing about being a man?
  16. What is your favorite meme on the internet?
  17. If you were locked in a small room with one song playing on a loop forever, which song would make you go insane fastest?
  18. What sounds like a euphemism, but isn’t one?
  19. What’s your favorite “dad joke?”
  20. If you had a catchphrase, what would it be?
  21. Who’s your favorite fictional villain?
  22. If you were given $10,000 to throw an event or party, what would it be like?
  23. What celebrity would you most hate to have dinner with?
  24. Would you rather meet your ancestors or your descendants?
  25. Have you ever walked out of a movie you paid money for?
  26. If you had a time machine to change one thing about history, what would it be?
  27. Have you ever met someone only once or twice, but they left a massive impression on you?
  28. Have you ever quit a job on the spot?
  29. What would you refuse to do for any amount of money?
  30. What would you put in your perfect sandwich?
  31. If you could only read one author for the rest of your life, who would you choose?
  32. What job could you lie your way into with no experience without anyone noticing?
  33. What is your least useful talent?
  34. Would you rather have the ability to pause or rewind your life?
  35. What’s the best prank you’ve ever played on someone?
  36. What three people would you want on your side during a zombie apocalypse?
  37. If you could become the most knowledgeable person in the world on any subject, what would you choose?
  38. If you had to choose the national anthem of Earth, what would it be?
  39. What ingredient or spice would you erase from existence?
  40. What is the most interesting fact you know?
  41. What’s the worst tattoo you’ve ever seen?
  42. Would you rather be able to speak every language or open any locked door?
  43. If you had to lose one of your senses, which one would you give up?
  44. What accessory or item of clothing do you own that people comment on most?
  45. If you had to give an hour-long lecture about anything right now, what would you choose?
  46. Who in your life do you think is most likely to become successful?
  47. What was the biggest “close call” in your life?
  48. What everyday thing do we do today that you think will be ridiculed in 30 years?
  49. If you could stay one age for the rest of your life, what age would you pick?
  50. If you were a wrestler, what would your entrance music be?
  51. If you could bring back one dead musical artist and watch them perform, who would you choose?

Heartfelt questions to ask a guy

happy couple laying on the grass

You’ve spoken enough to know that he ticks all the right boxes for you, and you enjoy his company. You’ve probably even asked a few flirty questions by now. If this is the case, you probably want to see if his views on relationships match yours. These more heartfelt questions can give you a more in-depth insight into his personality and whether he could be a good boyfriend.

  1. What do you daydream about most?
  2. Do you remember your first crush?
  3. How did you lose your virginity?
  4. Have you ever been in love with someone?
  5. What is the best thing about your life at the moment?
  6. Can you tell me something that you have never told anyone else?
  7. What person in the world are you closest to emotionally?
  8. What thing never fails to cheer you up when you’re feeling down?
  9. Have you ever had your heart broken?
  10. Would you rather have loved and lost or never to have loved?
  11. What things have you learned about yourself from past relationships?
  12. Are you still friends with any of your exes?
  13. What is the best compliment you have ever received?
  14. Do you have a “type”?
  15. What non-physical traits do you find most attractive?
  16. What famous person do you think I most look like?
  17. Do you prefer a party with lots of people or a deep conversation with one person?
  18. Do you consider a shared sense of humor important in a relationship?
  19. How important do you think monogamy is in a relationship?
  20. Do you think you can be in love with more than one person at the same time?
  21. When you’re feeling sad, do you prefer to be cheered up with attention or left alone?
  22. What is your favorite thing about yourself?
  23. What is your favorite thing about me?
  24. How would you describe “love“?
  25. Do you think there is a difference between loving someone and being “in love” with them?
  26. Do you believe in marriage, and do you think you will get married one day?
  27. What made you want to take me on a date?
  28. Are you interested in going on another date?

Non-judgemental questions to ask him

couple with paper planes

Dating can sometimes seem like a job interview or a sales pitch. Everyone is desperate to impress and hide their vulnerability. However, learning someone’s weaknesses, fears, or even just embarrassing fails can often be the thing that really brings the two of you closer. If you want to let the guy share his vulnerability without being judgemental, these questions are great to get him to open up.

  1. What thing aimed at children do you still enjoy?
  2. What’s your guiltiest pleasure?
  3. What would be the scariest sound to wake you up at night?
  4. Have you ever been incredibly stressed about something that turned out completely fine?
  5. What are you most tired of hearing about lately?
  6. What would you love to rant about without being judged?
  7. What was the strangest habit you had as a child?
  8. What did you ridicule until you tried it?
  9. What conspiracy theory do you believe in?
  10. Do you have any phobias?
  11. Do you prefer routine or spontaneity?
  12. What one item would you rescue from your house if it was on fire?
  13. Have you ever had a crush on a fictional character?
  14. What’s the weirdest experience you’ve had?
  15. What things do you like that are stereotypically feminine?
  16. What’s your worst customer service story?
  17. What purchase do you regret most?
  18. What’s the best “bad” decision you’ve ever made?
  19. How many phones have you lost or broken?
  20. If you were a corrupt dictator, how would you control your people?
  21. What’s the worst haircut you ever had?
  22. What sport or game are you worst at?
  23. What’s your funniest drunk story?
  24. Have you ever been naked in public?
  25. Have you ever had a “man-crush?”
  26. What would you say is your worst habit?
  27. What’s the stupidest thing you’ve ever done?
  28. When was the last time you cried, and what was the reason?
  29. What was the most trouble you ever got into at school?
  30. Have you ever been fired from a job, and if so, what was the reason?
  31. Have you ever been in trouble with the law, and if so, what was the reason?
  32. Have you ever had sex in a public place?

Deep questions to ask a guy

couple holding hands in a cafe

Sometimes things do get deep and meaningful. If you have really found comfort around a guy and feel like you could share anything with each other, these questions are great to reveal his inner values and the depths of his soul. Even if you just want to get a little philosophical and discuss the meaning of life as a way to pass the time, these are the right questions to ask a guy on a date.

  1. What do you doubt most in life?
  2. Do you love yourself?
  3. What makes you feel alive?
  4. Would you describe yourself as an independent person?
  5. What worries keep you up at night?
  6. Would you describe yourself as a family man?
  7. What do you miss most about your childhood?
  8. What do you think makes a place “home” to you?
  9. What stories from your life will you tell your grandchildren?
  10. What double standard do you think is the worst?
  11. What’s the most generous thing anyone has ever done for you?
  12. What qualities make someone a good friend?
  13. What frustrates you the most about the world?
  14. Do you like the culture that you were brought up in?
  15. What has changed the most about you since you were younger?
  16. If you could say one thing to yourself at age ten, what would you say?
  17. What one thing do you feel is missing from your life?
  18. Who is your worst enemy?
  19. Do you see yourself as more of a leader or a follower?
  20. Which do you think is more important: freedom or security?
  21. Do you consider yourself adventurous?
  22. Do you believe in fate?
  23. Do you believe that we have free will?
  24. What are you most ashamed of about yourself or your past?
  25. If you could change one thing about your past, what would you change?
  26. Do you believe men and women can ever be just friends with each other?
  27. How would you describe the concept of a “real man?”
  28. If you had to dedicate your life to one cause, what would it be?
  29. If you died right now, what would your greatest achievement be?
  30. Would you rather be alone or be with the wrong person?
  31. What is the highest pressure situation you have been in, and how did you get through it?
  32. Would you choose to live to the age of 500 if you could?
  33. What do you think about current politics?
  34. Which historical or political figure do you relate to most?
  35. Do you believe people can be born “evil” or do they become that way?
  36. If this was your last day on Earth, what would you do?
  37. Are you scared of death?
  38. Do you believe in a God or creator?
  39. Do you believe in an afterlife?

Asking questions on a date is a tried-and-true way of leading to a fun conversation, and learning about who your date is as a person. However, it is essential to avoid bombarding a guy with so many questions that he feels like he is at an interview.

An excellent way to avoid this is to let him ask you as many questions as you ask him. If he does this, he is a good conversationalist and probably worth seeing again. Ask the right questions at the right time, and you can really win him over!

Andy is a storyteller who loves good books and good jokes. In the rare moments he isn’t writing, you can find him jogging in the park or perfecting barbeque ribs.


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