Questions to Ask a Guy You Like

When you start dating a guy or when you like some guy and there’s a possibility of a relationship in the air, it would serve you and your future relationship best if you got to know him better; and the easiest way to getting to know someone is by asking questions. By asking questions and in essence talking, you get to know and appreciate the common grounds, the appreciable qualities, the tiny flaws as well as the major flaws in the person- all important if you are hoping to build a successful relationship.

Now, when I say ask questions, I definitely do not mean interrogate- a common mistake that many women end up doing. This is where the way you ask questions comes into play a major factor. When you are in the nascent stages of a relationship, and even if you are quite along that road, it is always better to ask questions in a way wherein they blend in with the general conversation at hand. Guys- as a matter of fact, no one – likes to be smothered with suffocating questions; all you do is, end up boring or scaring him- not an ideal thing to do if you really like the guy. So, girls do remember that the questions mentioned here will only be effective if you pick your moments to ask, pick your tone and most importantly, pick your timing. No guy wants to have to face heavy laden questions right from at the start itself – he knows there is always going to be time to face such dreaded questions if the relationship gets serious. You have to make sure that the questions you ask are easy, funny, intriguing and- most importantly- comfortable.  Here are some questions that will help you in judging and deciding if the guy you like likes you back, whether there is a scope for any future in the relationship and the level of comfort you share with him.


Icebreaker questions

  1. Which sports team do you support?
  2. What is your favorite movie/ actor?
  3. Do you read books, if so, what kind of books do you like?
  4. Where did you spend your childhood? What was it like growing up there?
  5. Where do you want to go on a holiday? Or Which is your favorite travel destination?
  6. The sexiest actress in the world?
  7. What do you do for a living? Tell me a little about your work.
  8. What is your secret desire? Have you ever wanted to be a woman?
  9. Is what you do, what you really want or is there something else that you would like to achieve in the future?
  10. What was the craziest thing that you have ever done?
  11. Tell me the most embarrassing thing that has ever happened to you?
  12. Who is your hero?
  13. What college/school did you attend? What did you graduate in?
  14. What do you miss about school or college?
  15. What do you consider as your best achievement?
  16. What kind of woman are you interested in? What is your concept of the perfect women?
  17. What is the best/ worst feeling that you have experienced till date?
  18. What do you think is the best attribute about you, physically?
  19. If you were an animal, what would you like to be?
  20. Sex or food- what would you give up?

Up close and personal questions

  1. What is the first thing that strikes you about a person, and most importantly about a woman?
  2. What was our last relationship like?
  3. What happened there, if it is not too much of me to ask?
  4. Which do you prefer- open or exclusive relationship?
  5.  Why would you a date a girl? What do you expect of her?
  6. What do consider as the perfect date? Have you ever had one?
  7. Do you believe soul mates exist?
  8. What’s your take on marriage? How long should you know someone before popping the question?
  9. When was your first kiss? When did you first do it?
  10. What did you think of me the very first time we met?
  11. Do you think that people deserve a second chance even if they have hurt you bad the first time?
  12. How close are you with your family?
  13. Do you own a pet? What are your pet peeves?
  14. Where do you see yourself in the next 5-10 years time?
  15. Tell me about your best friends and what they do?
  16. Do you have set goals and plans or do you make plans as you go?
  17. Do you think our relationship can go the distance and last?
  18. What infuriates or saddens you the most?
  19. What is the one thing that most people don’t know about you?
  20. Did a girl ever break your heart? What happened?

Random questions

  1. Do you have a nickname? If so, what?
  2. Have you ever helped someone secretly?
  3. What are you immensely proud of in your life?
  4. If you have a time machine, what part of your life would you go back to?
  5. Do you have any little weird thing/habit?
  6. Have you had sex at a public place?
  7. What was the funniest thing that has ever happened in your life?
  8. Do you prefer to live a hundred years melancholy or 10 super fun and adventure filled days?
  9. How do you normally spend your weekends?
  10. What was the best thing about being a kid that you still miss?

While all these questions are easy going and shed light into the character of the guy, remember that you might never know the truth of the matter unless you give the relationship a shot. Paying attention to his body language will also help you gauge a lot about him. These questions are aimed at helping you decide if you want to take that leap of faith, so as to speak.

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