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

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

Marcel Stevens

Marcel Stevens

Marcel has over 12 years in journalism who enjoys writing, jogging, reading and tennis.

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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 225 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

Finally, if you want a handy version of this article, we’ve included a downloadable and printable version of these questions at the end of this article.

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?

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?
Personal Questions to Ask a Guy: About How You View Yourself and Life | personal questions to ask a guy over text | personal questions to ask a guy dirty

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?
Personal Questions to Ask a Guy: About the Future | personal questions to ask a guy dirty | flirty questions to ask a guy

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 expendable?
  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?
Fun Personal Questions to Ask a Guy | flirty questions to ask a guy | dirty questions to ask a guy

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?
Fun, Sexy Question to Ask a Guy | dirty questions to ask a guy | fun questions to ask a guy

More Personal Questions to Ask a Guy

  1. What is your favorite question to ask a woman on a first date? Why is it your favorite question?
  2. What is your favorite movie, and why?
  3. What is your favorite book, and why?
  4. What is your favorite song, and why?
  5. What is your favorite type of music?
  6. What is the last concert or show you went to, and did you enjoy it?
  7. What is your favorite sport, and why?
  8. Do you play any sports? If so, which one do you play?
  9. Do you play an instrument? If so, which one do you play?
  10. Do you have a tattoo? What is it, and is there a meaning behind it?
  11. If you were to get a tattoo right now, what would it be, and why?
  12. Do you prefer girls with or without tattoos?
  13. Do you prefer girls with or without piercings?
  14. Do you smoke, or did you used to smoke?
  15. Do you prefer girls who don’t smoke?
  16. Should pineapple go on pizza, and why?
  17. Do you like to travel? If so, where have you traveled to, and what was your favorite destination so far?
  18. If you could go on a trip tomorrow to anywhere in the world, where would you go?
  19. Do you prefer the mountains or the ocean? Why?
  20. Do you have a vision board? If so, do you update it every year?
  21. Do you have a personal mission statement? If so, what is it?
  22. What is your favorite motivational quote?
  23. Do you have a mentor? Who is it?
  24. Who are your heroes? Why are they your heroes?
  25. What is your dream job/career? Has it always been your dream?
  26. What was your first job? Did you like it?
  27. Do you enjoy your current job, and why?
  28. Who would play you in a movie about your life?
  29. What commonly accepted view do you disagree with and why?
  30. Did you move around as a child or live in the same place throughout your childhood?
  31. How many places have you lived?
  32. Do you drink? If not, why?
  33. What is your favorite cocktail?
  34. Have you tried drugs? Which ones?
  35. Do you believe in the Law of Attraction? Why or why not?
  36. What does your dream house look like, and where is it?
  37. Have you ever lost a loved one? If so, who was it?
  38. What is the hardest thing you have ever been through?
  39. How do you deal with challenges?
  40. What is the scariest thing that has ever happened to you?
  41. Do you believe in ghosts? Have you ever seen one?
  42. Do you prefer to stay in or go out?
  43. Are you an introvert or extrovert?
  44. Do you own, or have you ever owned, a business?
  45. Do you have a best friend? Who is it?
  46. If you could have a superpower, what would you want it to be, and why?
  47. What three things would you want to have with you on a desert island?
  48. Do you enjoy cooking? If so, what is your best dish?
  49. What is your favorite food/meal?
  50. If you won the lottery and never had to work again, what would you do with your time?
  51. Do you like surprises? If not, why?
questions to ask a guy to know his intentions | questions to ask a guy to get to know him | more personal questions to ask a guy over text
  1. If a genie granted you three wishes, what would they be?
  2. Do you have a hobby? What is it?
  3. What is your favorite ice cream flavor?
  4. How do you relax when you are stressed?
  5. What are your political leanings, conservative or liberal?
  6. Do you think it is important that we believe in the same things politically?
  7. How do you feel about feminism? Do you fully understand it?
  8. What motivates or inspires you?
  9. What relationship advice would you give to your younger self?
  10. Did your parents get divorced or do/did they have a happy marriage?
  11. Do you have any bad habits? What are they?
  12. Do you have any expensive habits? What are they?
  13. Do you believe in aliens or think there is life on other planets?
  14. Have you previously been engaged or married? If so, for how long?
  15. Why didn’t your previous relationships work out?
  16. Are you still friends with any of your exes?
  17. What was your longest relationship?
  18. Does your family have any weird traditions? If so, what are they?
  19. Do you have a phobia, and what is it?
  20. Do you give to a charity? If so, which one, and why?
  21. What cause are you most passionate about?
  22. Do you have a pet? What is it and what did you name it?
  23. Who is your favorite person, and why?
  24. Did you go to college? Which one did you attend?
  25. What was your major in college?
  26. Have you ever been injured during sex? If so, how did it happen?
  27. What is your funniest pick-up line?
  28. If you could live in a different era, which one would it be and why?
  29. What is a food you like that others think is strange?
  30. What foods, if any, do you hate?
  31. What is your greatest strength?
  32. What is your biggest weakness?
  33. Do you ever have road rage?
  34. Are you a morning or a night person?
  35. Do you play video games? If so, how often?
  36. Do you have any collections? What are they?
  37. What is your favorite color?
  38. Are you more like your mom or your dad?
  39. Do you keep your home clean? Are you a clean freak?
  40. Are you organized or cluttered? If you are cluttered, do you wish you were more organized?
  41. What skill do you wish you had, and why?
  42. If you could time travel, where is the first place/time you would go, and why?
  43. What are you most proud of, and why?
  44. Do you ever talk to yourself? About what?
  45. Do you have a favorite word, and what is it?
  46. Where do you see yourself 5 years from now, or 10 years from now?
  47. Do you have a bucket list? If so, what is one thing on your bucket list?
  48. What is your love language? Have you read the book?
  49. Do you believe in second chances? Have you been given one or given someone else one?

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. 

If, however, you want to test how well you know each other, have some fun with this list of how well do you know me questions. Or if you just want some laughs, here are some funny controversial questions.

Finally, if you want a handy version of this article, then we’ve included a downloadable and printable version of these questions below. Just click the button to get free instant access to these 225 personal questions to ask a guy questions.

questions to ask a guy to know his intentions | questions to ask a guy to get to know him | questions to ask a guy over text

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