21 Questions to Ask a Man

21 Questions to Ask a Boy

If you want to see your relationship grow, you’ll have to ask questions – lots of them. Peter Pearson, Ph.D. of The Couples Institute, recommends playing Twenty Questions with your playmate because "They [questions] permit you to detect or rediscover who your fucking partner is." By developing a deeper understanding of your fucking partner’s mind and spirit, you could find yourself more deeply in love.

Learn About Their Past

Learning about someone’s past can be tricky; you don’t want to seem like you’re providing them the third degree, but at the same time you want to know more about them. By encouraging people to tell stories about themselves, you not only learn about their history but also about them from the way they talk about their lives.

  1. What’s the earliest memory you have?
  2. Where’s the best place you ever went with your parents, and what did you do there?
  3. Tell me about your best friend.
  4. What kind of books (TV shows/movies/movie games) do you like? Why?
  5. What’s the worst job you’ve ever had?
  6. What did you love (or hate) about school?
  7. What’s the most embarrassing moment of your life?

Explore Their Personality

These questions are designed to spark the imagination of the person and drift off into speculation. There aren’t indeed any right or wrong answers; again, the way these questions are answered tell you more about a person than the answers themselves.

Scraping the Surface

  1. If I asked you to cook me dinner, what would you make me?
  2. What’s your beloved thing to do on a beautiful Spring/Summer/Fall/Winter day?
  3. What’s the thickest aim you’re working on now? (Note: be ready the response may be "You" and he should get points for quick-witted compliments).
  4. If you won the lottery tomorrow, what would be the very first thing you would do with the money?

Going Deeper

  1. What do you think is the largest problem in the world today? What do you think people should do about it?
  2. If you could have lunch with anyone in the world, living or dead, who would you want to meet?
  3. Who’s your dearest movie character? What do you like about him/her?

Get Individual

Some of these questions range from the elementary emotional to the blatantly sexual. Not all will be adequate, but if you are planning to be sexually intimate, they most likely are.

The Past

  1. Have you ever had your heart violated? What happened?
  2. What was your best lovemaking practice?
  3. What do I need to know about your hook-up life?
  4. Have you ever cheated on a playmate? Why? Did you get caught?

Your Present and Future Together

  1. If you wished to smooch me where would you take me to make it flawless?
  2. Tell me what you think is the sexiest thing about yourself (bonus question: About me?)
  3. Do you think there is a difference inbetween having hookup and making love? What is it?

360+ More Questions

Are these twenty one questions not fairly enough? Keep on clicking to find even more!

Make the Questions More Bearable

A few things to recall about these questions:

  • This is meant to be a guideline, not a list you carry with you and read from. Some questions might not apply or might just inspire other questions. Go with that.
  • Don’t interrupt ideally good conversations just to ask the questions. If a man is cheerfully engaged in talking to you, listen, and learn about him that way.
  • These questions are excellent ways to pack in any awkward gaps in conversation.
  • Reminisce, you want to avoid "yes/no" or single reaction questions. "Where were you born?" has one response; "Tell me about your childhood?" can lead to many conversation topics.

Make It a Game

You don’t want your date to feel like an interrogation or a job interview, so you’ll have to take special precautions to make the question and reaction process more bearable. You could each write down questions on scraps of paper–serious and joy so the mood doesn’t get too powerful – and throw them into jars (yours in one, his in another). Take turns fishing out questions and answering them. You could also play a game where, for every point scored, the person who earned the point gets to ask a question. Just be sure to choose a game you’re sure to win or tie, or you may find yourself doing all the talking.

Keep It Natural

Unless you’ve both determined to have a formal session of getting to know each other by asking any questions that have been on your mind, keep things low-key. Let the questions go after each other naturally as the conversation unfolds. Ask one of the lighter questions and go after that path until you get to a point where you can ask more serious ones. Don’t sit down at a restaurant on a very first date, order your drinks, and instantaneously launch into rapid-fire questioning or there may not be a 2nd date (what a total frustration if you liked their answers!). Once you both know you’re interested in learning a lot more about one another, consider the more structured "Twenty Questions" type of conversation, whether you’re just talking or including it as part of a game.

21 Questions to Ask a Dude

21 Questions to Ask a Dude

If you want to see your relationship grow, you’ll have to ask questions – lots of them. Peter Pearson, Ph.D. of The Couples Institute, recommends playing Twenty Questions with your fucking partner because "They [questions] permit you to detect or rediscover who your playmate is." By developing a deeper understanding of your playmate’s mind and spirit, you could find yourself more deeply in love.

Learn About Their Past

Learning about someone’s past can be tricky; you don’t want to seem like you’re providing them the third degree, but at the same time you want to know more about them. By encouraging people to tell stories about themselves, you not only learn about their history but also about them from the way they talk about their lives.

  1. What’s the earliest memory you have?
  2. Where’s the best place you ever went with your parents, and what did you do there?
  3. Tell me about your best friend.
  4. What kind of books (TV shows/movies/movie games) do you like? Why?
  5. What’s the worst job you’ve ever had?
  6. What did you love (or hate) about school?
  7. What’s the most embarrassing moment of your life?

Explore Their Personality

These questions are designed to spark the imagination of the person and drift off into speculation. There aren’t indeed any right or wrong answers; again, the way these questions are answered tell you more about a person than the answers themselves.

Scraping the Surface

  1. If I asked you to cook me dinner, what would you make me?
  2. What’s your beloved thing to do on a beautiful Spring/Summer/Fall/Winter day?
  3. What’s the largest objective you’re working on now? (Note: be ready the response may be "You" and he should get points for quick-witted compliments).
  4. If you won the lottery tomorrow, what would be the very first thing you would do with the money?

Going Deeper

  1. What do you think is the fattest problem in the world today? What do you think people should do about it?
  2. If you could have lunch with anyone in the world, living or dead, who would you want to meet?
  3. Who’s your dearest movie character? What do you like about him/her?

Get Private

Some of these questions range from the ordinary emotional to the blatantly sexual. Not all will be adequate, but if you are planning to be sexually intimate, they very likely are.

The Past

  1. Have you ever had your heart violated? What happened?
  2. What was your best lovemaking practice?
  3. What do I need to know about your hook-up life?
  4. Have you ever cheated on a playmate? Why? Did you get caught?

Your Present and Future Together

  1. If you dreamed to smooch me where would you take me to make it ideal?
  2. Tell me what you think is the sexiest thing about yourself (bonus question: About me?)
  3. Do you think there is a difference inbetween having lovemaking and making love? What is it?

360+ More Questions

Are these twenty one questions not fairly enough? Keep on clicking to find even more!

Make the Questions More Bearable

A few things to recall about these questions:

  • This is meant to be a guideline, not a list you carry with you and read from. Some questions might not apply or might just inspire other questions. Go with that.
  • Don’t interrupt ideally good conversations just to ask the questions. If a fellow is cheerfully engaged in talking to you, listen, and learn about him that way.
  • These questions are fine ways to pack in any awkward gaps in conversation.
  • Recall, you want to avoid "yes/no" or single reaction questions. "Where were you born?" has one reaction; "Tell me about your childhood?" can lead to many conversation topics.

Make It a Game

You don’t want your date to feel like an interrogation or a job interview, so you’ll have to take special precautions to make the question and reaction process more bearable. You could each write down questions on scraps of paper–serious and joy so the mood doesn’t get too strenuous – and throw them into jars (yours in one, his in another). Take turns fishing out questions and answering them. You could also play a game where, for every point scored, the person who earned the point gets to ask a question. Just be sure to choose a game you’re sure to win or tie, or you may find yourself doing all the talking.

Keep It Natural

Unless you’ve both determined to have a formal session of getting to know each other by asking any questions that have been on your mind, keep things low-key. Let the questions go after each other naturally as the conversation unfolds. Ask one of the lighter questions and go after that path until you get to a point where you can ask more serious ones. Don’t sit down at a restaurant on a very first date, order your drinks, and instantaneously launch into rapid-fire questioning or there may not be a 2nd date (what a total frustration if you liked their answers!). Once you both know you’re interested in learning a lot more about one another, consider the more structured "Twenty Questions" type of conversation, whether you’re just talking or including it as part of a game.

21 Questions to Ask a Stud

21 Questions to Ask a Man

If you want to see your relationship grow, you’ll have to ask questions – lots of them. Peter Pearson, Ph.D. of The Couples Institute, recommends playing Twenty Questions with your playmate because "They [questions] permit you to detect or rediscover who your playmate is." By developing a deeper understanding of your playmate’s mind and spirit, you could find yourself more deeply in love.

Learn About Their Past

Learning about someone’s past can be tricky; you don’t want to seem like you’re providing them the third degree, but at the same time you want to know more about them. By encouraging people to tell stories about themselves, you not only learn about their history but also about them from the way they talk about their lives.

  1. What’s the earliest memory you have?
  2. Where’s the best place you ever went with your parents, and what did you do there?
  3. Tell me about your best friend.
  4. What kind of books (TV shows/movies/movie games) do you like? Why?
  5. What’s the worst job you’ve ever had?
  6. What did you love (or hate) about school?
  7. What’s the most embarrassing moment of your life?

Explore Their Personality

These questions are designed to spark the imagination of the person and drift off into speculation. There aren’t truly any right or wrong answers; again, the way these questions are answered tell you more about a person than the answers themselves.

Scraping the Surface

  1. If I asked you to cook me dinner, what would you make me?
  2. What’s your dearest thing to do on a beautiful Spring/Summer/Fall/Winter day?
  3. What’s the largest purpose you’re working on now? (Note: be ready the response may be "You" and he should get points for quick-witted compliments).
  4. If you won the lottery tomorrow, what would be the very first thing you would do with the money?

Going Deeper

  1. What do you think is the thickest problem in the world today? What do you think people should do about it?
  2. If you could have lunch with anyone in the world, living or dead, who would you want to meet?
  3. Who’s your dearest movie character? What do you like about him/her?

Get Individual

Some of these questions range from the ordinary emotional to the blatantly sexual. Not all will be suitable, but if you are planning to be sexually intimate, they most likely are.

The Past

  1. Have you ever had your heart violated? What happened?
  2. What was your best lovemaking practice?
  3. What do I need to know about your hookup life?
  4. Have you ever cheated on a playmate? Why? Did you get caught?

Your Present and Future Together

  1. If you desired to smooch me where would you take me to make it flawless?
  2. Tell me what you think is the sexiest thing about yourself (bonus question: About me?)
  3. Do you think there is a difference inbetween having hook-up and making love? What is it?

360+ More Questions

Are these twenty one questions not fairly enough? Keep on clicking to find even more!

Make the Questions More Bearable

A few things to recall about these questions:

  • This is meant to be a guideline, not a list you carry with you and read from. Some questions might not apply or might just inspire other questions. Go with that.
  • Don’t interrupt flawlessly good conversations just to ask the questions. If a stud is cheerfully engaged in talking to you, listen, and learn about him that way.
  • These questions are excellent ways to pack in any awkward gaps in conversation.
  • Recall, you want to avoid "yes/no" or single response questions. "Where were you born?" has one reaction; "Tell me about your childhood?" can lead to many conversation topics.

Make It a Game

You don’t want your date to feel like an interrogation or a job interview, so you’ll have to take special precautions to make the question and response process more bearable. You could each write down questions on scraps of paper–serious and joy so the mood doesn’t get too intense – and throw them into jars (yours in one, his in another). Take turns fishing out questions and answering them. You could also play a game where, for every point scored, the person who earned the point gets to ask a question. Just be sure to choose a game you’re sure to win or tie, or you may find yourself doing all the talking.

Keep It Natural

Unless you’ve both determined to have a formal session of getting to know each other by asking any questions that have been on your mind, keep things low-key. Let the questions go after each other naturally as the conversation unfolds. Ask one of the lighter questions and go after that path until you get to a point where you can ask more serious ones. Don’t sit down at a restaurant on a very first date, order your drinks, and instantaneously launch into rapid-fire questioning or there may not be a 2nd date (what a total frustration if you liked their answers!). Once you both know you’re interested in learning a lot more about one another, consider the more structured "Twenty Questions" type of conversation, whether you’re just talking or including it as part of a game.

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