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Getting to know someone can be a daunting task, especially if you don’t have much experience with it. You might not know what questions to ask or where to start. Luckily, we’ve got you covered!

These 250+ questions will help you learn more about the guy you’re interested in and create a deeper connection between you two. So what are you waiting for? Get started today!

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How to get to know a guy

Getting to know someone can be a nerve-wracking experience, especially if you don’t know what questions to ask. The beauty of getting to know someone is that the process never really ends. You can always learn more about a person, no matter how long you’ve been together!

Asking questions is a great way to show that you’re interested in someone and get the conversation going. We’ve compiled this huge list of questions to ask a guy!

Tips for first conversations

  1. Be confident! Do you know what’s hot as hell? Being confident. And if you’re not as confident, just act like you are. That’s the secret: Fake it ‘til you make it!
  2. Show interest! Everybody likes it when someone listens to their stories and experiences. Just listen and enjoy his stories!
  3. Be honest! You want to create a special bond with this guy, so don’t lie to him. Ever. Nobody likes liars.
  4. Don’t judge! Some of these questions are really personal and can lead to personal backstories. Just treat him the way you’d like to be treated.

Our collection of 250+ questions to ask a guy

We collected 250+ questions to ask a guy divided into six categories. You can use these questions to get to know a guy on a first date, at a bar, at work, or anywhere else!

Tip: If you want to play a game with these questions, check out our 21 questions game!

50 questions to ask a guy

Let’s start with some general questions to ask a guy. These questions can be used in almost any situation, from a first date to a casual hangout!

  1. If technology advances, would you try and give birth if that became possible?
  2. Would you rather have your grandfather’s hairstyle or first name?
  3. What’s your favorite season, and why?
  4. Do you think religion will always exist?
  5. What do you think about artificial intelligence?
  6. Would you rather go skiing in the winter or to the beach in the summer?
  7. If you were a girl for a day, what is the first thing you’d do?
  8. Have you ever been through an experience that you couldn’t explain?
  9. Would you rather surf in shark-infested waters or jump free-fall into the Grand Canyon with a parachute?
  10. How do you treat people who annoy you for no reason?
  11. Would you travel to a foreign country all by yourself?
  12. Would you rather have a horse’s tail or a unicorn horn?
  13. What do you miss about your childhood?
  14. What’s your least favorite name for a child?
  15. What do you wish people would stop asking you?
  16. Would you rather lose your sense of smell or taste?
  17. What was/is your favorite subject in school?
  18. Would you rather hold a snake or kiss a jellyfish?
  19. What is the most expensive thing you’ve ever bought?
  20. What’s the weirdest conversation you’ve ever overheard?
  21. What took you way too long to figure out?
  22. What’s the worst advice someone has given you?
  23. Would you rather always have your favorite song stuck in your head forever or always dream the same thing at night?
  24. What would you grab if your house was on fire?
  25. What would the exact opposite of you be like?
  26. Would you rather raise chickens for eggs or beef for meat?
  27. What was the biggest mistake in history?
  28. What alcoholic drink best describes your personality and why?
  29. Would you rather always have to skip everywhere or run everywhere?
  30. What does your name mean?
  31. What would you do if a guy asked for your number?
  32. Would you rather have a pig nose or a rat face?
  33. Would you like to be a stay-at-home dad?
  34. What’s an essential part of a friendship?
  35. Would you rather have hands instead of feet or feet instead of hands?
  36. What meal could you eat every day?
  37. What was your favorite toy as a child?
  38. Do you have a nickname? If you do, how did you get it?
  39. When was the last time you cried, and why did you?
  40. What’s the strangest gift you’ve ever received?
  41. What is your very first memory?
  42. What was the happiest moment of your life?
  43. What’s your ideal name for a child?
  44. Would you rather always smell rotten meat or always smell skunk?
  45. What childish thing do you still enjoy?
  46. What kind of food would you never try?
  47. How do you like your coffee?
  48. Would you rather live on a houseboat or in a cabin in the mountains?
  49. What’s the most interesting fact you know?
  50. Would you rather sit with a resting lion for ten minutes or run across a hungry alligator’s back?

50 first date questions to ask a guy

First dates can be both exciting and nerve-wracking. You want to make a good impression, but you don’t want to come off as being too interested or interrogating the guy! These first date questions are light and easy, but they’ll still give you a good idea of his personality.

  1. What’s the most exciting city you’ve ever visited?
  2. What’s the sweetest thing you’ve ever done for a girl?
  3. What is the first thing you notice about a woman?
  4. Have you ever gotten your heart broken?
  5. How old were you when you started dating?
  6. Who is your dream woman, dead or alive?
  7. What small thing makes you angrier than it should?
  8. How would your perfect partner treat you?
  9. What was the last concert you went to?
  10. Do you believe love can last a lifetime?
  11. What are some things you wish a girl knew before dating you?
  12. Which social media do you use the most often?
  13. What are some things people have selflessly done to make your life better?
  14. What do you find attractive in a woman?
  15. What’s the best thing about being single?
  16. What age do you wish you could permanently be?
  17. What makes a good life?
  18. What is one thing that you’re proud of?
  19. When you’re old, would you rather die before or after your spouse?
  20. What do you love most about sleeping with a girl?
  21. Where have you traveled?
  22. Would you rather be married to a 10 with a bad personality or a 6 with a fantastic personality?
  23. Would you rather have a cook or a maid?
  24. What were some of the turning points in your life?
  25. Are you still friends with your exes?
  26. How would you name your biography?
  27. What makes you special and unique?
  28. What do you really wish you knew when you were younger?
  29. How did you lose your virginity?
  30. Would you rather be too busy or be bored?
  31. Would you ever date a blind person?
  32. What do you really think about the relationship we have together?
  33. How did your last relationship end?
  34. What scares you the most about the future?
  35. What was the last movie that made you cry?
  36. What was your favorite game as a child?
  37. Do you think weight gain is an acceptable reason to break up with someone?
  38. Are women equal to men?
  39. What game or movie universe would you most like to live in?
  40. What’s the length of your longest romantic relationship?
  41. How would you explain what ‘love’ is?
  42. What’s your definition of a “real man”?
  43. What’s the most paranormal thing that has happened to you?
  44. Would you make breakfast in bed for a girl you fancy?
  45. If you were to write a book, what kind would it be?
  46. Do you think of me when I am not around?
  47. What would you tell your younger self if you could go back in time?
  48. What’s one thing about the opposite sex you’re attracted to?
  49. Would you date someone who doesn’t have any books in their house?
  50. What are your feelings towards open relationships?

25 random questions to ask a guy

Sometimes the best way to get to know someone is by asking random, unexpected questions! These questions can range from serious to lighthearted, and they can be a great way to break the ice.

N e w !
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  1. Would you rather be famous for your dancing or singing talents?
  2. What do you think of hairy legs?
  3. Would you rather play a villain or a hero in a movie?
  4. Which Disney Prince are you?
  5. Who is your secret hero?
  6. What’s the worst injury you’ve ever gotten?
  7. Would you rather watch the big game at home or live at the stadium?
  8. What’s the worst and best thing about being male?
  9. What’s the most expensive thing you own?
  10. What are your views on what happens after you die?
  11. What is the ugliest piece of clothing you own?
  12. Would you rather your only mode of transportation be a donkey or a giraffe?
  13. What was your first trip abroad?
  14. Would you rather be a stand-up comedian or a concert pianist?
  15. Would you rather win an Olympic Gold Medal or an Academy Award?
  16. Would you rather be the youngest or the oldest sibling?
  17. What’s the most illegal thing you’ve done?
  18. What’s one job you would never do?
  19. Would you rather be too hot or too cold?
  20. Would you rather work in a group or work alone?
  21. Would you rather be forced to dance every time you heard music or be forced to sing along to any song you heard?
  22. Would you rather be on a game show or star in a soap opera?
  23. What would be your perfect breakfast?
  24. Would you rather be a famous movie star or a favorite popular music group member?
  25. What really annoys you when other people do it, but you occasionally do it well?

25 funny questions to ask a guy

Next, we have some funny questions to ask a guy! If you’re looking to make things a little more lighthearted on your date or with your friends, these are the perfect questions.

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🤓 Suggested read: 250+ Questions to get to know someone

  1. Would you rather date a woman five years younger or older than you?
  2. What’s the worst place you’ve ever vomited in?
  3. Would you rather never be stuck in traffic again or get another cold?
  4. What’s the weirdest thing you’ve said to yourself?
  5. What is the best joke that you know?
  6. What’s the most ridiculous tattoo you’ve ever seen?
  7. What would be your weapon of choice in a zombie apocalypse?
  8. What’s the most ridiculous thing you’ve done because you were bored?
  9. What is the craziest thing you’ve ever done?
  10. What was the worst situation you ever laughed in?
  11. What is the stupidest situation you almost got killed in?
  12. When was the most inappropriate time you farted?
  13. Would you rather live without the internet or without AC and heating?
  14. What was your first drunken experience?
  15. If you could throw up on one person, who would it be?
  16. Would you rather lose all your money and valuables or all the pictures you have ever taken?
  17. Would you rather not shave your beard or cut your hair for a month?
  18. What would you bring to a desert island if you could only bring three things?
  19. Would you rather eat a box of dry spaghetti noodles or two cups of uncooked rice?
  20. When and how did you find out that Santa isn’t real?
  21. What’s the most ridiculous argument you’ve had?
  22. Would you rather be able to control fire or water?
  23. Would you rather never use social media sites/apps again or never watch another movie or TV show?
  24. What’s the strangest hobby you’ve heard of?
  25. Which fictional character would you marry if you had the chance?

25 sexual questions to ask a guy

These sexual questions to ask a guy are designed to get him to open up and reveal more about himself. These questions can be a little deeper and more personal than the first batch, but they’ll really help you get to know him!

  1. What place on my body do you think is the most sensitive?
  2. What word sounds sexy to you?
  3. What do you think of threesomes?
  4. Would you rather have one partner or multiple partners?
  5. What’s the best thing I can do for you in bed?
  6. What does your ideal one-night stand look like?
  7. What do you wear when you sleep?
  8. In your opinion, what does it mean to be good in bed?
  9. What do you think an orgy would be like?
  10. Would you rather grant everyone’s sexual wishes or have all your sexual wishes granted?
  11. Do you like BDSM?
  12. What’s your secret sexual fantasy?
  13. What is it about us girls that makes you so horny?
  14. Do you remember what that first orgasm felt like?
  15. What turns you on?
  16. Is there anything you won’t do in bed?
  17. What’s your favorite porn category?
  18. Would you rather have your hair pulled or slapped on the butt?
  19. What’s the wildest sexual thing you’ve ever done?
  20. What’s the most sensitive place on your body?
  21. Did you ever fall asleep during sex?
  22. What’s the sexiest movie you’ve ever watched?
  23. What’s the most number of times you’ve done it in a row?
  24. Would you describe yourself as naughty? Why do you say so?
  25. Would you rather pay for sex or be paid to have sex?

25 deep questions to ask a guy

These deep questions to ask a guy are the perfect way to get to know someone on a deeper level. If you want to create a closer connection with someone, these questions are a great way to start!

  1. If you won the lottery tomorrow, what would be the first thing you would do with the money?
  2. What are five things you can’t live without?
  3. What language do you like the sound of, even though you don’t know how to speak it?
  4. How do you think the world will look in 30 years?
  5. Would you rather be completely insane and know that you are insane or completely insane and believe you are sane?
  6. What was the best day of your life so far?
  7. Should drugs be legal? If yes, under what conditions? If no, why?
  8. How different was your life one year ago?
  9. What language would you like to speak fluently?
  10. What do you hate about politicians?
  11. What was the best gift you’ve ever given to someone?
  12. Would you rather lose the ability to read or lose the ability to speak?
  13. Are drugs necessarily bad, or is it just the people who tend to use them?
  14. Do you think there is life after death? What about life before life?
  15. If you could put something on the cover of a newspaper, what would it be?
  16. Would you rather be stuck on an island alone or with someone who talks incessantly?
  17. If you could witness any event of the past, present, or future, what would it be?
  18. How do you think the pyramids were built?
  19. Have you ever had to lose someone close to you?
  20. What would your dream bedroom look like?
  21. Would you rather be able to see 10 minutes into your own future or 10 minutes into the future of anyone but yourself?
  22. Do you think Avril Lavigne is dead?
  23. If you could have dinner with one person, living or dead, who would it be?
  24. Would you rather always be 10 minutes late or 20 minutes early?
  25. If you went into a coma and woke up in the year 2120, what would be the first thing you would want to know?

Bonus: 21 Questions Game to ask a guy

The 21 Questions game is a great way to get to know someone without feeling like you’re interrogating them. These questions can be used on almost any guy, from your best friend to your cute co-worker!

📖 Suggested read: 20 Questions: Conversation Starter Game | Gameplay

  1. What’s the most embarrassing thing you’ve ever done to get someone’s attention?
  2. How much honesty do you need in a relationship?
  3. What do you personally think of your friend’s relationships?
  4. Would you rather have a home on the beach or in the mountains?
  5. How much money do you think a country is worth?
  6. What makes you the angriest?
  7. What’s the strangest way you’ve become friends with someone?
  8. What is the meaning of cheating for you?
  9. Have you ever had a crush on an animated character?
  10. Would you still like a girl if she was way taller than you?
  11. How attractive do you think you are on a scale from 1 to 10?
  12. Would you rather move to a new city or town every week or never be able to leave the city or town you were born in?
  13. Do you believe in aliens?
  14. What was the best meal you’ve ever eaten?
  15. Would you rather live without electricity or without your best friend?
  16. How did you meet your best friend?
  17. What makes you insecure?
  18. What does love look like to you?
  19. What do you think about having kids?
  20. What TV shows did you watch when you were a kid?
  21. Which actor would play you in a movie about your life?

👉 Follow this link for 100+ more Questions for the 21 Questions Game!

Looking for more dating advice? Check out these books for more tips on finding the perfect partner and making your relationships last:

  1. Boundaries in Dating: How Healthy Choices Grow Healthy Relationships
  2. Love: The Psychology of Attraction: A Practical Guide to Successful Dating and a Happy Relationship
  3. Seriously, This Is Online Dating?: How to Love Yourself Harder and Date Smarter
  4. Single, Dating, Engaged, Married: Navigating Life and Love in the Modern Age
  5. Gay Dating, your guide to finding love: The essential read for every gay man
  6. The Science of Happily Ever After: What Really Matters in the Search for True Love
  7. Things You Should Already Know About Dating, You F*cking Idiot
  8. How to Not Die Alone: The Surprising Science That Will Help You Find Love
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