125 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 125 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? 
  10. Did you regularly attend religious services as a child? If so, who took you? Parents? Grandparents? Another relative?
  11. Did you have a pet growing up? If so, what kind? If not, did you resent your parents for not having one? Would you want one now?
  12. What was your favorite tv show as a child?
  13. If you could choose one song that summed up your childhood, what would that song be?
  14. Did you have more same sex or opposite friends growing up? Did that change as you got older?
  15. Were you closer with your mom or your dad?
  16. Were you insecure about anything as a child?
  17. Did you have any siblings?
  18. What age were you when you had your first kiss?
  19. Who was the most influential teacher you ever had? Were they also your favorite teacher?
  20. If you could go back in time and pick one friend from childhood to spend another magical day with, who would you pick? How old would you be?
Personal Questions to Ask a Guy: About Childhood Memories & Dreams | questions to ask a guy to know his intentions | questions to ask a guy to get to know him

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?
  10. Do you have any regrets about the way you’ve treated someone?
  11. Do you rank physical appearance above inner beauty when seeking out a relationship?
  12. Do you see yourself being monogamous for the rest of your life?
  13. Are you happy with the person you are?
  14. Do you ever feel depressed?
  15. Do you ever pretend to be someone you’re not, or enjoy something you don’t particularly care for, to impress another person?
  16. Are you a religious person?
  17. If the people in your life were asked to describe you in just one word, what word do you think they’d choose?
  18. Do you consider yourself smarter than most people?
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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?
  13. Do you have a retirement destination in mind?
  14. Would you prefer to spend your retirement working less, doing something you love? Or just relax?
  15. Do you ever worry about how or when you are going to die?
  16. If you had a LGBTQ child, would you mind?
  17. Would you rather your child pursue higher education or forego it to do what makes them happy?
  18. Do you think it’s important for a child to start working as soon as they are able, to contribute to the home or save for what they want?
  19. What age would you consider to be too old for your child to move back into your house?
  20. If your parents were to suddenly tell you that you were adopted, what would you do?
  21. What would your perfect marriage be like? Would it mean being married to someone who wanted to spend every second together? Or one that believed in personal space and separate hobbies?
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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?
  9. Have you ever said something to intentionally push someone’s buttons and create a reaction?
  10. Do you fight dirty? Hit below the belt when in an argument?
  11. Are you the type to hold your feelings in and then blow up days, even weeks or months later after something possibly unrelated triggers your resentment?
  12. Have you ever talked to a therapist or priest?
  13. Do you ever question a moment in your life that seems wrong now, but maybe didn’t then?
  14. Were you ever in trouble with the law?
  15. Have you ever been attracted to an underage child?
  16. Do you ever picture someone else while making love to your partner?
  17. Do you enjoy pornography? If so, what type?
  18. What is your take on gentleman’s clubs?
Personal Questions to Ask a Guy: About Difficult Topics | questions to ask a guy to get to know him | questions to ask a guy over text

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?
  11. Do you have a ticklish spot?
  12. Have you ever watched a movie you’re too embarrassed to admit you liked?
  13. Do you ever dance in front of your mirror?
  14. Do you have a “signature move” that you use on dates?
  15. Which celebrity would you be if you could trade lives?
  16. If your favorite fast food chain suddenly had all zero calorie meals, with the same exact flavor, would you eat there more often? Which chain would you pick?
  17. If you could switch bodies with one family member or friend for a day, who would you pick and why?
  18. If you could play any sport professionally, which would it be?
  19. If you woke up suddenly having one new ability or talent, what would you want that to be?
  20. What is one game you don’t know how to play but would like to learn?
  21. Do you consider yourself an artistic person?
  22. What is one talent you’ve kept hidden from most people?
  23. Do you believe in love at first sight?
  24. What is one extreme sport or activity you wouldn’t mind trying?
  25. Which historical figure do you admire the most?
  26. Would you rather be a sinner or a saint?
  27. What, if anything, in your life do you consider to be expendible?
  28. Would you give up the love of your life for all the money in the world?
  29. Do you think that most men marry their mothers?
  30. If your parents didn’t like who you were dating, would you end it?
  31. Which vacation would you consider more fun: Disney World, relaxing on a tropical island or traveling around Europe?
  32. Did you ever want to learn to ride a motorcycle?
  33. What’s your guilty pleasure?
  34. If you could eat or drink one thing without ever gaining weight from it, what would it be?
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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?
  8. What is your favorite sexual position?
  9. Do you enjoy giving oral pleasure?
  10. Do you ever touch yourself while I’m laying asleep next to you?
  11. Would you be turned on if I woke you in the middle of the night to have sex?
  12. Would you ever go to a gentlemen's club with me?
  13. Would you go into a sex shop with me to pick out clothes and toys?
  14. If I offered to dress up as anything or anyone in the bedroom, which outfit would you pick?
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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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125 Personal Questions to Ask a Guy to Start a Deep Conversation