Learning more about someone is a time consuming effort. But, for women who are looking to ensure that the guy they are seeing is compatible, then a question and answer session is the best way to go. Though this may not seem super romantic, it is a great way to find out if the guy you are seeing is someone who has the same attitude and goals as you do, which makes many women wonder: What are good questions to ask a man? There are 20 questions that are going to help you learn more about the mind, the ideals and the goals of any guy that you may be just meeting or have been seeing for some time.

20 Questions to Ask a Guy—Background

The idea of learning about someone’s past is one that will take time. As you will find that if you start to interrogate the person, they may feel as though you are too concerned over their past. Instead, there are some questions that are going to help spur on the conversation, while also helping to learn more about the past of the someone that you may be seeing.

1. What is the first thing that you remember from your childhood?

2. What is the place that you went with your parents that gives you the fondest memories?

3. Who is your best friend and what makes him/her your best friend?

4. What are some of your favorite books, TV shows, video games, or movies and what makes them your favorites?

5. What is the job you've had that you consider to be the biggest mistake ever?

6. What did you enjoy most or hate about school?

7. What is the moment in your life that is the most embarrassing?

8. What is the unique thing you have eaten that is really weird?

9. What is your favorite shirt/clothing item?

10. Are you a coffee or tea drinker?

11. In any given week, how long do you spend on social networking sites?

12. The last relationship you were in, how did this end?

13. What is one of the worse things that you have ever done?

14. What are the top five pet peeves that you have?

15. Have you ever gotten drunk and blamed being drunk on something you said or an action that hurt someone else?

16. To have fun, where would you go?

17. How would you describe the relationship that you have with your parents?

18. What song or sound makes you happy just by hearing it?

19. What are your nicknames and how did you get them?

20. Do you consider yourself close with extended family members?

20 Questions to Ask a Guy—Personality

When you use these 20 questions, you are going to learn more about their personality type. This can help to determine if their personality is a match for you or not. These are good questions to ask guys, as there are no right or wrong answers, it is all about learning more about the guy in question.

1. In your opinion what is the biggest issue the world is facing today and what should we do about it?

2. Who would you want to have lunch with today, if it could be anyone living or dead throughout history?

3. What movie character do you like the best, and why do you like him or her?

4. If you had to cook dinner for me, what would you serve?

5. It is a beautiful day during any given season, what would you want to do?

6. What is the biggest goal that you have right now and are working towards?

7. You win the lottery, so what is the first thing you do with the money that you won?

8. What is the one aspect that you hate most about yourself?

9. If you had to change one thing about yourself, what would it be?

10. If you have to choose between being two times smarter or two times happier, which would it be?

11. If you could live anywhere in the entire world, where would it be?

12. What is the thing that you want to experience and would be disappointed if you never got the chance?

13. If you only had one week to live, what would you do?

14. Do you feel as though everyone should watch the news daily to stay up to date with what is going on everywhere?

15. If you had to give one person a present and you have an unlimited budget, who would you give a present to and what would it be?

16. What are your feelings when your best friend starts spending more time with his new girlfriend rather than with you?

17. Do you get bored a lot?

18. Do you ever get the feeling that you are being watched at random times?

19. What is the one physical characteristic that you would change about yourself?

20. What job would you consider as your dream job?

20 Questions to Ask a Guy—Intimacy

When getting to know someone, the 20 questions that concern intimacy are not appropriate in every sitting. However, for those who are going to be physically active with the guy, then these questions are something that you will want and need to know before going through with this.

1. Has your heart ever been broken? If so, what happened?

2. If you were planning on kissing me, where would be your perfect place to do this?

3. What experience would you say is your best lovemaking experience?

4. What are the things that I need to know about your sex life?

5. Have you ever cheated on someone? If so, why and did you get caught?

6. What do you consider the sexiest thing about you?

7. Do you believe there is a difference between sex and making love? What is it?

8. Is physical and emotional intimacy dependent upon one another or can you have one without the other?

9. What household chores are you unwilling or resistant to do?

10. If I had lipstick on my teeth or my hair was sticking up, would you tell me?

11. Has someone ever caught you naked?

12. In your opinion, does size really matter?

13. How many days could you abstain from sex or masturbation if you had no choice but to do this?

14. Do you want numerous relationships at the same time?

15. Would you like to role play that I am some animal and you are the poor hunter chasing after me?

16. Between me and your best friend, who would your choice be?

17. Do you think about the first love that you had?

18. Do you friends say good things about me?

19. Have you ever eavesdropped or spied on me?

20. If you knew that I had a crush on you, what would you do?

  • There may be times in which this list of questions are not appropriate for every situation, these are simply meant as a guideline.
  • Do not jump to conclusions with his answers. Instead, take a few days to listen to the answers that he gave and look at the deeper meaning.
  • What is important to you in a relationship? This can help to gauge what answers you want from the 20 questions to ask a guy, and determine whether this guy meets your standards or not.
  • Remember to be willing to compromise on some things, but you need to rank which items you can compromise on and which are concrete.
  • Do not quiz the guy. If the guy is talking to you, do not interpret him to ask these questions.
  • Try to avoid questions that can be answered with yes or no, as you want questions that will lead to conversations.

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