50 questions for guys.

50 Question to ask a Guy

Do you have a guy in your life that is hard to understand? Do you want to know more about him but don’t know where or how to start? There are some serious and fun, but they’re all meant to get you better acquainted with him. 

A lot of people have become interested in improving their relationships with others, especially guys. However, there can sometimes be barriers – such as language or culture- where they might feel uncomfortable asking certain essential things for establishing rapport and understanding one another better.

In a relationship that’s going on for a while, it’s time to spice things up and have some fun. A conversation does not aim to impress another person but to learn about them. Unfortunately, most people don’t take this approach, so dating can be so stressful and overwhelming. Being who you are is not enough.

You have to be who you think the other person wants you to be. If you want to create a positive impression, don’t imagine what they look like or see in you. My method for having a great time, bonding, and gaining a man’s trust is to ask the following questions.

Some are lighthearted and silly, and others are serious and force him to share his true self, creating intimacy and a genuine connection. People often struggle with connecting and bonding, something nearly all of us work within this current era. Have fun going through the list with a guy you like, and jot down your favorites. Take a look at this list of 50 questions.

The actual or false question is very personal. But, unfortunately, some people use it for their purposes. 

  1. Which of your physical characteristics do you find most attractive?
  2. How would you rate my personality?
  3. What would you be like if you could switch jobs right now?
  4. What three words will you use to describe yourself?
  5. What would be your ideal date/girl?
  6. Have you ever taken a fabulous vacation?
  7. Which country do you want to visit?
  8. Is camping your idea of a good time, or do you prefer clubbing?
  9. What is your greatest fear?
  10. How have you ever treated a woman nicely?
  11. Which is the most remarkable thing a woman has ever done for you?
  12. What’s the sexiest part of a woman you are most attracted aout?
  13. Most special childhood memories?
  14.  What is your biggest pet peeve?
  15. The most significant achievement you have made thus far?
  16. Which feature of your home is your favorite?
  17. Why do you dislike living in your current location?
  18. What foods can you not live without?
  19.  What is the one gift you would most like to receive?
  20.  Would you prefer a gift certificate or money on your birthday?
  21.  Which is your strongest personality trait, and why?
  22. What is one thing you wish you could go back in time and do again?
  23.  Do you have a favorite place where you go to relax?
  24. Which is most appealing to you: exercise at home or the gym?
  25. Have you ever cried over something?
  26. If a woman did something that you couldn’t forgive her for, what would it be?
  27. How do you feel about being betrayed by a friend?
  28. Do you have a favorite thing about your friends?
  29. Who is your best friend? How did you meet her/him/them?
  30. When you first meet a woman, what is the first question you always ask her?

A guy’s answer is sometimes a mystery; it’s hard to guess what’s behind their answers. So here are some questions that are like a riddle when the answers.

  1. What is your childhood dream?
  2. If you will have kids in the future, how many do you plan?
  3. Have you ever been in trouble?
  4. Do you prefer a beach vacation or an urban getaway?
  5. Would you like someone if they didn’t like you back?
  6. What would be your dream car?
  7. Which is your favorite book?
  8. What is your most minor favorite film ever?
  9. Do you ever wish you had superpowers?
  10. How do you spend time with your friends?
  11. How much time do you prefer spending with your mother or father?
  12. Among your family members, who is your favorite?
  13. Is there anything you’ve done that you think is impressive?
  14. Is there anything weird about your habits?
  15. Where were you afraid of; being alone in the dark or losing your way?
  16. Is there anything you would never spend money on?
  17. Do you have a favorite annual event?
  18. Which is your favorite season, and why?
  19. Is there something you worried about, and it turned out not to be a big deal?
  20. Any embarrassing or memorable moments when you were a teen?

Additionally, you can talk about games,music, movies, and food! Little conversations are always a starte. So make the most of it and take notes of every answer too!


Asking a guy out can be scary and intimidating, but we’re here to help! It doesn’t matter if you’ve known him for years or just met him at the grocery store this morning. There’s nothing wrong with asking that cute guy on a date. The best way to know if he might say yes is by knowing what questions to ask before you do so. 

These 50 essential questions will get your conversations started and allow you two plenty of time to find those commonalities that make dating each other so enjoyable. Once again, take it slow – one question at a time. What are some of your go-to conversation starters? If all else fails, I think these fifty should provide enough material for an hour-long chat session filled with laughter.