21 Revealing Questions to Ask a Guy

Crystal Schwanke
21 Questions to Ask a Guy

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 partner because, "They [questions] allow you to discover or rediscover who your partner is." By developing a deeper understanding of your partner's mind and spirit, you could find yourself more deeply in love.

Learn About Their Past (Questions 1-6)

Learning about someone's past can be tricky; you don't want to seem like you're giving 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/video games) do you like? Why?

5. What's the worst job you've ever had?

6. What did you enjoy (or hate) about school?

Explore Their Personality (Questions 7-13)

These relationship questions to ask a guy you just met like are designed to spark the imagination of the person and drift off into speculation. There aren't really any right or wrong answers; again, the way these questions are answered tell you more about a person than the answers themselves and are great questions to ask when online dating, too.

Scratching the Surface

Consider these good questions to ask a guy before dating him to learn his personality:

7. If I asked you to cook me dinner, what would you make me?

8. What's your favorite thing to do on a beautiful Spring/Summer/Fall/Winter day?

9. What's the biggest goal you're working on now? (Note: be prepared the answer may be "You" and he should get points for quick-witted compliments).

10. If you won the lottery tomorrow, what would be the first thing you would do with the money?

Going Deeper

Serious questions to ask a guy include:

11. What do you think is the biggest problem in the world today? What do you think people should do about it?

12. If you could have lunch with anyone in the world, living or dead, who would you want to meet?

13. Who's your favorite movie character? What do you like about him/her?

Get Personal (Questions 14-21)

Some of these 21 questions to ask a boy range from the simple emotional to the blatantly sexual. Not all will be appropriate, but if you are planning to be sexually intimate, they probably are.

The Past

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Questions to ask before dating seriously might include:

14. Have you ever had your heart broken? What happened?

15. What was your best lovemaking experience?

16. What do I need to know about your sex life?

17. Have you ever cheated on a partner? Why? Did you get caught?

Your Present and Future Together

Questions to ask a guy about relationships in the future might include:

18. If you wanted to kiss me, where would you take me to make it perfect?

19. Tell me what you think is the sexiest thing about yourself (bonus question: About me?)

20. Do you think there is a difference between having sex and making love? What is it?

21. How do you think aging will affect your attraction to me?

How to Keep the Conversation Going

These questions should elicit more questions from you and shouldn't merely be a quick checklist of questions. Ask for elaboration when appropriate and if your guy is particularly brief when answering a question, you may want to ask some follow-up questions to get more details. For example, if "What do I need to know about your sex life?" is met with a grunt and shrug, ask more questions specific to this one. "If there was a movie about your sex life, what would be the defining scene?" might be the phrasing he needs to give you a more extensive response.

360+ More Questions

Are these 21 questions to ask a man not quite enough? Keep on clicking to find even more questions to ask when dating!

Make the Questions More Bearable

Make the Questions More Bearable

A few things to remember about these questions to ask while dating:

  • Don't ask questions via text that you expect to get lengthy responses to. Some questions are fine for quick text conversations (such as those featured in "Scratching the Surface"), but more in-depth questions should be saved for face-to-face conversations or telephone if you're in a long-distance relationship.
  • This is meant to be a guideline, not a list you carry with you and read from. Some questions to ask a guy before dating might not apply or might just inspire other questions. Go with that or use them as conversation starters with a guy.
  • Don't interrupt perfectly good conversations just to ask the questions. If a guy is happily engaged in talking to you, listen and learn about him that way.
  • These questions are great ways to fill in any awkward gaps in conversation, and many are great online dating questions.
  • Remember, you want to avoid "yes/no" or single answer questions to ask someone you want to date. "Where were you born?" has one answer; "Tell me about your childhood?" can lead to many conversation topics with a guy.

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 answer process more bearable. You could each write down 21 questions for dating on scraps of paper--serious and fun so the mood doesn't get too heavy - and throw them into jars (yours in one, his in another). Take turns fishing out dating questions to ask a guy 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.

Rules of the Game

If your guy is competitive, he may be more willing to participate if you make it a game with rules and points. As mentioned above, write the questions on slips of paper and put them in a jar or bowl. Select a question and ask it; if he answers, he gets a point. If he decides to pass on the question, he doesn't get the point and you get to ask another question before it's his turn. He'll have a bowl full of questions for you too, so take turns in asking and answering questions. The best way to win is to answer all the questions, and the quickest way to lose is to pass on answering, so it's to his benefit if he answers all the questions the first time. The first person to 21 points wins.

Keep It Natural

Unless you've both decided 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 follow each other naturally as the conversation unfolds. Ask one of the lighter questions and follow that path until you get to a point where you can ask more serious ones. Don't sit down at a restaurant on a first date, order your drinks, and immediately launch into rapid-fire questioning or there may not be a second date (what a total disappointment if you liked their answers!). Once you both know you're interested in learning a lot more about one another, consider having a more structured 21 questions with a guy conversation, whether you're just talking or including it as part of a game.

21 Revealing Questions to Ask a Guy