325 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 325 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?
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 few words, but they also can stir up further conversation! (Also, if you're interested in similar content, here are 107 funny yes or no questions you can ask in a 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?

Questions About Childhood Memories & Dreams

  1. What's one thing you'd change about your childhood?
  2. If you played make believe, who did you pretend to be (superhero, relative)?
  3. What's your worst childhood memory?
  4. What's something that children have today, that you wish you had as a child?
  5. If you could, would you change the number of siblings you had as a child? If yes, what would you change it to? Why?
  6. Were you ever bullied, or did you ever bully someone else?
  7. Did you ever cheat in school? If so, what happened?
  8. How old were you when you had your first crush?
  9. How old were you when you had your first girlfriend?
  10. Is there anything you did that your parent(s) still don't know about, that you'd like to confess to your parents, but you're still afraid to do so?
  11. What's something embarrassing that happened to you that you either never told anyone, or you're careful to only tell a select few?
  12. How did you learn about the birds and the bees (sex)?
  13. Is there an event that happened in your childhood that you think is most responsible for shaping who you are today?
  14. Did you want to be more like your mom or dad (personality, job choice, how others treat them)?
  15. Did you ever have times when you wished you were a part of another family? 
  16. Did you ever run away from home or seriously plan to run away?If so, why, and where did you go or plan to go? 

Questions About How You View Yourself and Life

  1. What do you want your legacy to be?
  2. Do you think couples should share passwords with each other?
  3. Do you think men and women can just be friends?
  4. Who's someone you can talk to about anything?
  5. What's one thing you've had to do or have done, but would never do again?
  6. Could you date someone who eats differently from you? So, if you're a meat eater, could you date a vegan, or vice versa?
  7. What are your top deal-breakers in a romantic partner/relationship?
  8. What's the most dangerous thing you've ever done or experienced?
  9. Have you ever dated someone that a relative or close friend dated? Would you ever?
  10. Do you consider yourself emotionally intelligent? 
  11. Have you ever made a big mistake, then realized afterwards it was actually beneficial? If so, what was it and what happened that made you see it as a good thing?
  12. If you could ask your parents one thing about their parenting or relationship with you as a child or adult, what would it be?
  13. If you could change something about how your parents raised you, what would it be? And what is the impact on your life you'd hope the change would have?
  14. Do you believe everything happens for a reason? Or, do you believe people assign reasons to things to make themselves feel better or more in control of life?
  15. When you were a child, what fantasy did you dream of experiencing as an adult, that you still secretly wish you could experience?
  16. Do you prefer someone cheer you up, join you in your misery, or leave you alone when you're in a bad mood?
  17. What are some unfavorable things people have said about you that you can now admit are or were true?

Questions About the Future 

  1. How will you know when you're ready to get married?
  2. How do you feel about adopting a child?
  3. If you could find out something about your future, what would you want to know?
  4. What do you think the future holds for us and our relationship? 
  5. What are your financial goals?
  6. What one thing do you most want to do before you die?
  7. In what ways do you hope to grow and develop as a person in the next year?
  8. What are two things you want to accomplish in the next year?
  9. What would you like to change about your relationship with your parent(s) going forward?
  10. If you could be transported into your future, what age or event would you want to be transported to (it can't be your death or its cause)? 
  11. What age do you think is too old to still have children?
  12. If you could be visited by someone from the future, who would it be (U.S. President, yourself)? 
  13. Would you stay with your spouse if her physical or mental qualities changed drastically (weight, lost a limb, experienced mental illness)?
  14. What advice would you give your daughter when she starts dating?
  15. What would you do if you found out there was no heaven or hell, higher power, or consequences for your actions while alive once you die?

Deep Questions About Difficult Topics 

  1. If you were married and your wife could no longer have sex, what would you do? Would you leave?
  2. Have you ever been cheated on?
  3. Have you ever cheated on someone?
  4. Would you leave your spouse if she cheated?
  5. Have you ever had a one-night stand?
  6. What would you do if you found out your romantic partner lied to you about something very essential to who you thought she was?
  7. How do you feel about the legalization of marijuana?
  8. Would you ever date a recovering addict?
  9. Do you believe in the death penalty?
  10. What would you do if you found out your spouse committed a crime?
  11. If you had to pick a past romantic partner or someone you really liked, to still be with today, who would it be and why? Do you know where that person is today?
  12. What's one thing you'd change about our relationship?
  13. What's something that I do that really bothers you, but you're afraid to tell me, or haven't told me yet?
  14. What's something you feel your parents have done to screw you up that you would love to confront them about (if you had the guts)?
  15. What's something you'd like to ask me, but are afraid to ask?
  16. Have you ever committed a crime or been arrested?
  17. Have you ever been addicted to anything (food, gambling, sex)?

Fun Questions 

  1. How would you describe your sense of humor?
  2. Who's your favorite comedian?
  3. What's your favorite comedy movie and TV show?
  4. Have you ever played a prank or practical joke on someone? If yes, what was it?
  5. Is there a commercial or chick flick that makes you cry?
  6. If your spouse got a sex change operation, would you stay or leave?
  7. Have you ever had someone play a funny prank or practical joke on you? If yes, what happened?
  8. What's the cheapest date you've ever taken someone on?
  9. Under or over (toilet paper hanging)?
  10. If we were going to commit crimes together, what would they be?
  11. If you could be a fly on the wall, whose wall would you be on?
  12. What would you do if you had to go a week without your cell phone?
  13. What would be the soundtrack for a movie about your life?
  14. Do you have a nickname known only to your family/friends?
  15. What's something you do alone that you would be embarrassed to do in front of others?
  16. What's the funniest or craziest lie you've ever told to get out of doing something you didn't want to do?
  17. Have you ever had a crush on a relative or one of your parents' friends?
  18. What's the most unprofessional thing you've ever done at work?

Fun, Sexy Questions to Ask

  1. Have you ever “swung,” or traded sexual partners with someone?
  2. Have you ever listened in on someone having sex?
  3. What's the funniest and most embarrassing thing that's ever happened to you during a sexual encounter?
  4. Have you ever had sex in a public place?
  5. What's your best sexual skill when it comes to giving a woman an orgasm (oral, hands, penetration, other)?
  6. Have you ever had a three-some?
  7. Have you ever gone to a nude beach? If not, would you?
  8. When you're home alone, do you walk around naked?
  9. How do you feel about PDA (public displays of affection)?
  10. Do you watch porn?
  11. Are you more of a giver or receiver in the bedroom?
  12. Have you ever gotten caught having sex?
  13. If I showed up at your job butt naked under my trench coat, what would you do? 
  14. Do you have a favorite stripper move, or a move you'd want to see a stripper or woman perform?
  15. Do you have any fetishes?
  16. When did you lose your virginity?
  17. What part of a woman's body turns you on the most?

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. 

Also, if you want to discover more questions you can ask, here are a few articles to check out:

Finally, if you want to ask better questions, then watch this short, 20-minute course to learn how to have a great conversation with virtually anyone.

personal questions to ask a guy | deep personal questions to ask a guy | personal questions to ask a guy to get to know him
325 Personal Questions to Ask a Guy to Start a Deep Conversation