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Personal Questions to Ask a Guy

What are some personal questions to ask a guy?

Here’s a harsh reality, people are very lonely. A simple question can go a long way in creating a potential connection. If you’re a guy or a girl and want to establish and long-lasting relationship with another man, you’ll be looking to determine exactly how to do that.

Disclaimer: If you’re feeling lonely and are struggling to find the right information available to you on this website, please seek the help of a licensed therapist or counselor who can help you to address what might be troubling you. For a good resource, visit the Mental Health America’s list.

My experience with building friendships/relationships…

If you’re asking any type of questions to a person you want to build a friendship with, then my story is for you… I was awkward. An odd little kid who maybe didn’t connect with too many adults or other children…

I wanted friends pretty badly! I mean, very badly! Learning the right types of questions to ask to build relationships was the key for me… And I hope it is for you, too!
My best tip! It only takes 30 seconds of courage to ask someone a question and see where it goes. Remember that!

How to get personal with a guy

—Personal questions to ask a guy

It’s quite simple to develop a connection with a man. I hate to suggest that it’s harder with women, although it is. Men appreciate being noticed just as much as women. And to make them feel seen, questions that are tailored to their lifestyle will do better than generic prompts.

Spend time learning about the person you’re interested in before you go further. Action steps before you start asking questions:

  • What are their hobbies?
  • What do they spend their time doing?
  • What are they interested in?
  • Who do they spend time around?

While it might seem a little creepy, all you’re doing is getting an idea of who the person is before you start asking questions.

Related: Questions to ask your friends

A recent study by Harvard reported that 36% of all Americans feel “serious loneliness.” Many of which (almost 33% of that group) revealed that they don’t feel like they have close friends. Whether your a man looking to connect with another man. Or a woman looking to connect with a man. Understand that most people are feeling disconnected and would welcome your inquisition about their lifestyle or person.

Personal questions to ask a guy
Personal questions to ask a guy

In short, life is beautiful, don’t be afraid to try and make connections. Yes, rejection hurts, although it is a common part of building relationships with any person.

Related: Questions to ask your crush

When is the right time to ask personal questions

To better set yourself up for success, it’s best to ask personal questions when the moment is right. For example, a bad moment would be when the two of you are passing each other in the hallway (assuming you’re in high school).

This scenario would set the situation up for failure since the two of you won’t have enough time to start a meaningful conversation.

Here are some ideas to ensure that the timing is right:

  • Ask the other person out for coffee.
  • Ensure the two of you have enough time to have a meaningful conversation.
  • Use moments when the attention of the other person is directly on you
    • I.e., avoid situations where they are looking at their phone.

15 deep questions to ask him

If you’re already aware of who they are and are ready to jump right into getting personal, try a few of these prompts:

  1. What’s something that happened in your childhood that truly defined who you are today?
  2. What’s something that’s inspiring you today?
  3. Where do you picture your life being in the next 5-years?
  4. How do you handle those situations if things don’t go according to plan?
  5. Do you have anyone in your life that you would say is a negative influence?
  6. Who best defined who you are today, your mother or your father?
  7. What are your thoughts on religion? Do you practice religion?
  8. What parts of modern society are not doing us any good?
  9. What do you like to spend your free time doing that would never become a career?
  10. If you were put into a wheelchair tomorrow, how do you think that you would handle that situation?
  11. Where do you hope that your life never ends up going?
  12. What would be your greatest fear in life, and how would you avoid it?
  13. Where do you go when you’re feeling sad?
  14. Where do you like to go when you’re feeling the happiest?
  15. What brings you joy right now?
Personal questions to ask a guy
Personal questions to ask a guy

15 really personal questions to ask him

Maybe your intentions are to get flirty (assuming you’re someone trying to get to know the other person for more than friendship purposes). Try some of these very personal questions that are slightly dirty, slightly sexy, and could lead to something more:

  1. What’s the best way that you like to feel loved?
  2. Who was the last crush that you had? Who was it?
  3. What was your last relationship like and why did it end?
  4. Who do you find the most attractive?
  5. Which parts of a guy/girl do you find to be the most attractive?
  6. If someone were to touch one body part of yours, which part would you like to get touched?
  7. When is the last time that you felt butterflies in the pit of your stomach?
  8. Can men and women truly be “just friends?”
  9. If someone thought that you were really handsome and attractive, would you want them to tell you?
  10. Did you ever have a crush on a teacher?
  11. What’s the dirtiest thing that you’ve ever done?
  12. Did you ever make out with someone at your high school?
  13. Who was the first person that you kissed and what was it like?
  14. When you picture yourself growing old with someone, what do they look like?
  15. What’s the sexiest thing that’s ever happened to you? And how did it change you?

How to deliver the best personal question prompt to a guy

Trying to build a connection with someone is challenging. Yes, it is! Although, here are some simple tips that can help to increase your chances of getting a positive response.

1. Be confident

Keep your prompt short and sweet. Be confident in your delivery. He’ll see that.

Related: Questions to ask a guy over text

2. Make eye contact

Don’t keep your eyes down to the left or not facing him. Make direct eye contact when asking the question.

Related: Questions girls are afraid to ask guys

3. Be prepared for a response

Fold your hands, listen closely, and let him speak. Listen carefully to the words he’s expressing and use that as your method for continuing the conversation.

Fact checked:
Board reviewed by Marianne Tomlinson, LCSW (Couples and Family Therapy). Content is rigorously reviewed by a team of qualified and experienced fact checkers. Learn more.

About the author

Ryan Sanderson (LCSW) Ryan is a game and relationship enthusiast who enjoys all things quizzes, games, fun, love, relationships, and family. He's a licensed social worker and helps families, couples, and children in need. He's spoken about love and relationships on Salon.com, Forbes, and Mirror, to name a few.

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