55 Personal Questions to Ask a Guy to Start a Deep Conversation

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As you’re getting to know someone who you are seriously interested in, it’s a good idea to have some “go-to” personal questions to ask a guy. 

These inquiries can be exciting, deep, sexy, but they should all be asked in an effort to get to know him better.

So it’s important that you know what to ask as well as how to sit back and listen to the answers to give you real insight into this person’s mind.  

In this article, we will profile 55 personal questions you can ask a guy you’re trying to get to know.

Many of these questions are geared towards a more deep connection so you should use them only if you’ve already been together for a little while. They’re not the “just-for-fun” type of thing that you’d use as ice breakers for new friends or at orientations for school or work. 

Also, the questions may be on different subjects, but they have something in common – they’re meant to foster more trust between you so that you grow as a couple

Let’s get started…

Questions About Childhood Memories & Dreams 

  1. What’s one of your favorite memories growing up? 
  2. Who did you look up to the most and why? 
  3. Did you prefer to spend time with one friend or a big group of people?
  4. What did you want to be when you grew up?
  5. How important was it that you go to family gatherings and stay close to family members? 
  6. What was your favorite vacation you went on as a kid and why? 
  7. What were you most afraid of? 
  8. What was your favorite toy/book/movie/collectible and do you still have it? 
  9. Did you have a lot of the same habits and behaviors or have you changed a lot? 
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Questions About How You View Yourself and Life 

  1. What’s your best quality? 
  2. What’s one thing you’d like to change about yourself? 
  3. What one thing in your life do you regret the most? 
  4. Can you tell me a secret you haven’t told anyone? 
  5. What’s something you’ve always wanted to do that’s scary? 
  6. Are you happy with your career path or think you might make a change? 
  7. What’s something that you find unattractive in a person? 
  8. What’s one hobby you’d like to try if you didn’t have to worry about time or money? 
  9. Is there a habit you’d like to change in your everyday life?
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Questions About the Future  

  1. Do you see yourself getting married and what type of wedding? 
  2. Do you want kids and if so, how many? 
  3. Would you rather live in the city, suburbs, or country? 
  4. In what ways do you think our relationship and lives in general will change after marriage and kids? 
  5. Do you plan to retire by a certain age or want to work for as long as you’re physically able? 
  6. What is one big goal you want to reach by 30/40/50 (insert age)?
  7. What’s your belief/philosophy when it comes to raising kids? 
  8. How important is it for you to have extended family around and how much interaction and effect should your own family have with them? 
  9. What role do you plan on having (need to work out of the home, don’t mind staying at home with kids, etc.)? 
  10. Is it crucial to have “friends’ nights” where you get together without your family/kids? 
  11. Do you want to become “best friends” with your child or keep yourself as the provider/disciplinarian? 
  12. How do you want to be viewed as a parent? 
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Deep Questions About Difficult Topics

  1. What do you think about couples counseling (even if we’re not having serious problems)?
  2. Do you prefer to avoid conflict and not talk through issues if there’s a big relationship struggle? 
  3. Are you good with compromise or see it as giving in too much? 
  4. Do you let how others view you affect your opinion of yourself? 
  5. Would you like me to give space when you’re working on everyday challenges or do you like a lot of support? 
  6. Have you ever had any destructive habits that have gotten in the way of living your life? 
  7. What supports do you have or like to have when you’re in a rough spot? 
  8. What was the last thing that made you cry? 
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Fun Questions 

These questions may be simple and someone can answer with a word (or a few), but they also can stir up further conversation!

  1. What are you looking forward to tomorrow or this week/month? 
  2. What are the little things that have always made you smile? 
  3. If you ever won the lottery, what’s the thing you’d have to buy first?
  4. What’s your idea of the perfect date? (maybe you’ll find you’ve already done it…) 
  5. If you could live in only one country/state/region the rest of your life, what would it be? 
  6. What activity is the most private for you (that you like to do alone)?
  7. What’s your pet peeve that people do? 
  8. What’s the best compliment you’ve gotten?  
  9. What’s the one superpower you think would help for your life situation? 
  10. What have you been most grateful for lately? 
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Fun, Sexy Question to Ask

  1. Are you comfortable “talking dirty”? What does that mean for you? 
  2. What is your top sexual fantasy? 
  3. Are you comfortable with watching certain types of videos with me? 
  4. Are you okay with bringing props into the bedroom? 
  5. What do you think of slow, sensual sex? 
  6. Do you prefer a more dominant role or submissive? 
  7. Will you bring up any issues you have with our sexual experiences? 
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Final Thoughts on Personal Questions to Ask a Guy

I like to start out new relationships with a simple game of “20 Questions”. As the relationship develops, the questions get more complex and into the big issues and values of life. It can be difficult to figure out when to start asking. I think that it’s ideal to begin when you know you have a connection and want to spend a lot more time with the person. 

The above personal questions will allow you to find out more you can connect to and develop a sense of greater trust

So spend a date night or weekend getting into many of the questions with that special guy in your life. 

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