504 Personal Questions to Ask a Guy to Know Him on a Deeper Level

You have found our incredible collection of personal questions to ask a guy. Sometimes it’s difficult to get a guy to open up. Many boys are more emotionally guarded than girls. However, when they do share, you get to experience an entirely new, unexplored aspect of them.

Using these personal questions to ask a guy is one of the simplest methods to learn more about them. You can dig deeper and ask more personal inquiries after you’ve covered the fundamentals through small talk.

You can learn more about a guy you’re dating by using these personal questions to ask a guy. His responses will show a lot about him, from his views on love to his definition of success.

You may not always agree with him or share his opinions, but you will undoubtedly have a better understanding of his thoughts and worldview.

Most Personal Questions to Ask a Guy

Would you like to know someone better? Looking for personal questions to discuss with a guy? We’ve created some most personal questions to ask a guy or someone you’re dating that can deepen your connection.

1. What’s been your highest point in life so far?

2. What’s been your lowest point in life so far?

3. What makes you emotional?

4. What makes you stressed?

5. Do you believe in a higher power?

6. If you had the power to know the date of your death, would you want to know?

7. What are you most grateful for?

8. Is there anything you would change about yourself if you could?

9. Who inspires you the most?

10. Does being rich and famous appeal to you?

11. What’s the biggest risk you’ve ever taken?

12. What’s the biggest thing you’ve ever given up?

13. What’s the angriest you’ve ever been?

14. What’s the nicest thing you’ve ever done for somebody?

15. How would you describe your childhood?

16. Do you have any unresolved issues with your family?

17. How do your best friends describe you?

18. Do you trust easily?

19. What’s a secret you’ve never told anybody?

20. What did you learn from your last relationship?

21. How many girls have you told “I love you”?

22. Have you ever cheated in a relationship?

23. What is your greatest life goal?

24. What do you want for yourself in five years? In 10 years? 25 years?

25. Do you see me in your future?

26. How do you feel in yourself and your life right now? Is there anything you wish you could change, or anything you wish you had?

27. Do you usually express how you feel, or keep your emotions hidden? Why / why not?

28. What emotions do you find most difficult to deal with? And what kind of feelings do you crave the most?

29. When are you happiest and what makes you feel truly happy?

30. What makes you feel loved? And how do you think that affects your relationships?

31. What have your past relationships taught you? And do you have any regrets about how you’ve behaved in relationships before?

32. What are you passionate about? And why are you so passionate about it? Where does this passion come from? And what does it mean to you?

33. Do you think about the future much? What about it excites you and what about it scares you? And why?

34. Where do you see yourself in 5 years time? Or more specifically, where would you most like to see yourself, do you think you will get there, and what would stand in your way of not?

35. Are there any things you wish you had the courage to do? Or any things you secretly want to do or have, but are too afraid / embarrassed to put yourself out there and say it?

36. What kind of life do you want to live? What would a perfect future look like to you?

37. How often do you feel overwhelmed?

38. What will immediately disqualify a potential SO?

39. How adventurous are you? Give some examples.

40. Who do you want to be more like?

41. When was the last time you really panicked?

42. Where do you go when you want to be alone?

43. What chokes you up when you think about it?

44. How politically involved are you?

45. What is a controversial opinion do you have?

46. What fact do you try to ignore?

47. If you see a homeless person asking for money, do you give them any?

48. Do you prefer to spend more time with your SO, family, or friends? Why?

49. What activity calms you down and makes you feel at peace with the world?

50. Do you think any part of your personality needs to be improved? If so, which part and why?

51. Which aspect of your life is going really well right now and which aspect could you use some help with?

52. What was the most awkward conversation you ever had with someone?

53. What holidays did your family really go all out for when you were growing up?

54. Would you rather spend the day at an art, history, or science museum?

55. What seemed normal in your family when you were growing up, but seems weird now?

56. What’s your favorite tear jerking scene in a movie?

Super Personal Questions to Ask a Guy

A personal question is one that relates to the individual’s private life. Asking him irrational questions that may pertain to any guy will keep him on his toes. Therefore, use these super personal questions to ask a guy to know your guy better.

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. What’s your best quality?

12. What’s one thing you’d like to change about yourself?

13. What one thing in your life do you regret the most?

14. Can you tell me a secret you haven’t told anyone?

15. What’s something you’ve always wanted to do that’s scary?

16. Are you happy with your career path or think you might make a change?

17. What’s something that you find unattractive in a person?

18. What’s one hobby you’d like to try if you didn’t have to worry about time or money?

19. Is there a habit you’d like to change in your everyday life?

20. Do you have any regrets about the way you’ve treated someone?

21. Do you rank physical appearance above inner beauty when seeking out a relationship?

22. Do you see yourself being monogamous for the rest of your life?

23. Are you happy with the person you are?

24. Do you ever feel depressed?

25. Do you ever pretend to be someone you’re not, or enjoy something you don’t particularly care for, to impress another person?

26. 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?

27. What was your favorite tv show as a child?

28. If you could choose one song that summed up your childhood, what would that song be?

29. Did you have more same s#x or opposite friends growing up? Did that change as you got older?

30. Were you closer with your mom or your dad?

31. Were you insecure about anything as a child?

32. Did you have any siblings?

33. What age were you when you had your first kiss?

34. Who was the most influential teacher you ever had? Were they also your favorite teacher?

35. 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?

Very Personal Questions to Ask a Guy

You both need to have some level of confidence in your relationship to be able to respond to these very personal questions to ask a guy that you couldn’t ask just anyone. Check them out!

1. Are you a religious person?

2. If the people in your life were asked to describe you in just one word, what word do you think they’d choose?

3. Do you consider yourself smarter than most people?

4. Do you see yourself getting married and what type of wedding?

5. Do you want kids and if so, how many?

6. Would you rather live in the city, suburbs, or country?

7. In what ways do you think our relationship and lives in general will change after marriage and kids?

8. Do you plan to retire by a certain age or want to work for as long as you’re physically able?

9. What do you think about couples counseling (even if we’re not having serious problems)?

10. Do you prefer to avoid conflict and not talk through issues if there’s a big relationship struggle?

11. Are you good with compromise or see it as giving in too much?

12. Do you let how others view you affect your opinion of yourself?

13. Would you like me to give space when you’re working on everyday challenges or do you like a lot of support?

14. Have you ever had any destructive habits that have gotten in the way of living your life?

15. What supports do you have or like to have when you’re in a rough spot?

16. What was the last thing that made you cry?

17. Have you ever said something to intentionally push someone’s buttons and create a reaction?

18. Do you fight dirty? Hit below the belt when in an argument?

19. 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?

20. Have you ever talked to a therapist or priest?

21. What is one big goal you want to reach by 30/40/50 (insert age)?

22. What’s your belief/philosophy when it comes to raising kids?

23. How important is it for you to have extended family around and how much interaction and effect should your own family have with them?

24. What role do you plan on having (need to work out of the home, don’t mind staying at home with kids, etc.)?

25. Is it crucial to have “friends’ nights” where you get together without your family/kids?

26. Do you want to become “best friends” with your child or keep yourself as the provider/disciplinarian?

27. How do you want to be viewed as a parent?

28. Do you have a retirement destination in mind?

29. Would you prefer to spend your retirement working less, doing something you love? Or just relax?

30. Do you ever worry about how or when you are going to die?

31. If you had a LGBTQ child, would you mind?

32. Would you rather your child pursue higher education or forego it to do what makes them happy?

33. 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?

34. What age would you consider to be too old for your child to move back into your house?

35. If your parents were to suddenly tell you that you were adopted, what would you do?

36. 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?

Really Personal Questions to Ask a Guy

Finding entertaining questions to ask a guy might be challenging. You should only utilize these really personal questions to ask a guy after a brief period of time has passed because many of them are designed toward a deeper connection.

1. Do you ever question a moment in your life that seems wrong now, but maybe didn’t then?

2. Were you ever in trouble with the law?

3. What’s the one superpower you think would help for your life situation?

4. What have you been most grateful for lately?

5. Do you have a ticklish spot?

6. Have you ever watched a movie you’re too embarrassed to admit you liked?

7. Do you ever dance in front of your mirror?

8. Do you have a “signature move” that you use on dates?

9. Which celebrity would you be if you could trade lives?

10. 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?

11. If you could switch bodies with one family member or friend for a day, who would you pick and why?

12. If you could play any sport professionally, which would it be?

13. If you woke up suddenly having one new ability or talent, what would you want that to be?

14. What is one game you don’t know how to play but would like to learn?

15. Do you consider yourself an artistic person?

16. What is one talent you’ve kept hidden from most people?

17. Do you believe in love at first sight?

18. What is one extreme sport or activity you wouldn’t mind trying?

19. Which historical figure do you admire the most?

20. Would you rather be a sinner or a saint?

21. What, if anything, in your life do you consider to be expendable?

22. Would you give up the love of your life for all the money in the world?

23. Do you think that most men marry their mothers?

24. If your parents didn’t like who you were dating, would you end it?

25. Which vacation would you consider more fun: Disney World, relaxing on a tropical island or traveling around Europe?

26. Did you ever want to learn to ride a motorcycle?

27. What’s your guilty pleasure?

28. If you could eat or drink one thing without ever gaining weight from it, what would it be?

29. What are you looking forward to tomorrow or this week/month?

30. What are the little things that have always made you smile?

31. If you ever won the lottery, what’s the thing you’d have to buy first?

32. What’s your idea of the perfect date? (maybe you’ll find you’ve already done it…)

33. If you could live in only one country/state/region the rest of your life, what would it be?

34. What activity is the most private for you (that you like to do alone)?

35. What’s your pet peeve that people do?

36. What’s the best compliment you’ve gotten?

37. Have you ever been attracted to an underage child?

38. Do you ever picture someone else while making love to your partner?

39. Do you enjoy pornography? If so, what type?

40. What is your take on gentleman’s clubs?

Deep Personal Questions to Ask a Guy

Ask deep questions if you want to know a guy well. You’ll discover more about his intentions. We’ve put together a list of deep personal questions to ask a guy for you as a guide.

1. How do you deal with challenges?

2. What is the scariest thing that has ever happened to you?

3. Do you believe in ghosts? Have you ever seen one?

4. Do you prefer to stay in or go out?

5. Are you an introvert or extrovert?

6. Do you own, or have you ever owned, a business?

7. Do you have a best friend? Who is it?

8. If you could have a superpower, what would you want it to be, and why?

9. What three things would you want to have with you on a desert island?

10. Do you enjoy cooking? If so, what is your best dish?

11. What is your favorite food/meal?

12. If you won the lottery and never had to work again, what would you do with your time?

13. Do you like surprises? If not, why?

14. If a genie granted you three wishes, what would they be?

15. Do you have a hobby? What is it?

16. What is your favorite ice cream flavor?

17. How do you relax when you are stressed?

18. What are your political leanings, conservative or liberal?

19. Do you think it is important that we believe in the same things politically?

20. How do you feel about feminism? Do you fully understand it?

21. What motivates or inspires you?

22. What relationship advice would you give to your younger self?

23. Did your parents get divorced or do/did they have a happy marriage?

24. Do you have any bad habits? What are they?

25. Do you have any expensive habits? What are they?

26. Do you believe in aliens or think there is life on other planets?

27. Have you previously been engaged or married? If so, for how long?

28. Why didn’t your previous relationships work out?

29. Are you still friends with any of your exes?

30. What was your longest relationship?

31. Does your family have any weird traditions? If so, what are they?

32. Do you have a phobia, and what is it?

33. Do you give to a charity? If so, which one, and why?

34. What cause are you most passionate about?

35. Do you have a pet? What is it and what did you name it?

36. Who is your favorite person, and why?

37. Did you go to college? Which one did you attend?

38. What was your major in college?

39. Have you ever been injured during s#x? If so, how did it happen?

40. What is your funniest pick-up line?

41. If you could live in a different era, which one would it be and why?

42. What is a food you like that others think is strange?

43. What foods, if any, do you hate?

44. What is your greatest strength?

45. What is your biggest weakness?

46. Do you ever have road rage?

Good Personal Questions to Ask a Guy

A fantastic method to get to know a guy better and deepen your connection is to ask him personal questions. Make sure your questions are well-structured to continue the conversation in that direction. After reading through this list of good personal questions to ask a guy, you’ll undoubtedly have plenty material to speak about for the rest of the night.

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?

Dirty Personal Questions to Ask a Guy

Do you wish to spice the conversation? Use these dirty personal questions to ask a guy that will stimulate the curiosity of the guy you are interested in. They’re not the kind of activities you’d do “simply for fun” to make new acquaintances or during school or work orientations.

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 s#x?

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 s#x?

12. Would you ever go to a gentlemen’s club with me?

13. Would you go into a s#x 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?

Flirty Personal Questions to Ask a Guy

Some individuals naturally flirt. Some people may overthink it to the point of losing all motivation. Use these flirty personal questions to ask a guy that will make him blush if you want to flirt but are uncertain of how to make your intentions clear.

1. Would you rather be considered sexy or smart?

2. What is something about you that would surprise me?

3. What did you first notice about me?

4. What was your first kiss like?

5. What’s one question you’re dying to ask me?

6. How many times have you been in love?

7. If you had to use one movie title to describe your kissing style what would it be?

8. Little spoon or big spoon?

9. What is one temptation you can never resist?

10. How would someone usually let you know that she likes you?

11. Do you like a woman that is soft and sweet or more assertive?

12. How would you describe yourself in 3 words?

13. How would you describe me in 3 words?

14. Do you prefer staying in or going out?

15. What do you think your best feature is?

16. Have you ever made a really romantic gesture?

17. Would you rather date someone smart or hot?

18. How many people are you crushing on right now?

19. What’s the farthest you’ve gone on a first date?

20. What did you think when you first saw me?

21. What’s your biggest turn off?

22. What’s your biggest turn on?

23. Do you like when a woman flirts with you?

24. Did you do anything interesting today, well besides talking to me?

25. Who would you want to play your love interest in a movie about your life?

26. If we went on a date, what would it look like?

27. What do you think about before you fall asleep?

28. So what do you think we should do this weekend?

29. Do you enjoy being in a long term relationship?

30. If yes, what do you most like about being in a relationship?

31. If you could be famous for anything what would it be?

32. What’s a gift you’ve always dreamed of receiving?

33. When are we going on our next date?

34. What puts you in a good mood?

35. Would you rather that I was naughty or nice?

36. Have I made it into any of your dreams yet?

37. What is a favorite movie of yours that I would be surprised that you like?

38. What wins you over more… brains or beauty?

39. Would you rather end a date with a kiss or with a little bit of mystery?

40. What have you always imagined doing with a girlfriend that you’ve never done?

Weird Personal Questions to Ask a Guy

Many of these weird personal questions to ask a guy are a little ridiculous, and some are a little odd, but they are all pretty different. Therefore, you have to be able to identify at least a couple weird questions to ask a guy that will be appropriate for the guy.

1. Have you ever “swung,” or traded sexual partners with someone?

2. Have you ever listened in on someone having s#x?

3. What’s the funniest and most embarrassing thing that’s ever happened to you during a sexual encounter?

4. Have you ever had s#x 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 s#x?

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?

Serious Personal Questions to Ask a Guy

Asking the guy you like these serious personal questions to ask a guy will help you get to know him better. We’re confident you’ll discover at least some that will result in some genuinely intriguing answers.

1. Are you a morning or a night person?

2. Do you play video games? If so, how often?

3. Do you have any collections? What are they?

4. What is your favorite color?

5. What’s one thing you’d change about your childhood?

6. If you played make believe, who did you pretend to be (superhero, relative)?

7. What’s your worst childhood memory?

8. What’s something that children have today, that you wish you had as a child?

9. If you could, would you change the number of siblings you had as a child? If yes, what would you change it to? Why?

10. Were you ever bullied, or did you ever bully someone else?

11. Did you ever cheat in school? If so, what happened?

12. How old were you when you had your first crush?

13. How old were you when you had your first girlfriend?

14. 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?

15. What’s something embarrassing that happened to you that you either never told anyone, or you’re careful to only tell a select few?

16. How did you learn about the birds and the bees (s#x)?

17. Is there an event that happened in your childhood that you think is most responsible for shaping who you are today?

18. Did you want to be more like your mom or dad (personality, job choice, how others treat them)?

19. Did you ever have times when you wished you were a part of another family?

20. 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?

21. Are you more like your mom or your dad?

22. Do you keep your home clean? Are you a clean freak?

23. Are you organized or cluttered? If you are cluttered, do you wish you were more organized?

24. What skill do you wish you had, and why?

25. If you could time travel, where is the first place/time you would go, and why?

26. What are you most proud of, and why?

27. Do you ever talk to yourself? About what?

28. Do you have a favorite word, and what is it?

29. Where do you see yourself 5 years from now, or 10 years from now?

30. Do you have a bucket list? If so, what is one thing on your bucket list?

31. Have you read the book?

32. Do you believe in second chances? Have you been given one or given someone else one?

Embarrassing Personal Questions to Ask a Guy

It takes ample time to get to know someone. But it also requires work. If there is a guy in your life that you want to get to know better, you’ll need to use strategies other than politeness and small conversation. These embarrassing personal questions to ask a guy can do a magic for you!

1. When was the last time you cried?

2. How many girls have you slept with?

3. Have you ever seen your mom/sister/grandma naked?

4. Are you sure you’re not gay?

5. Do you love me?

6. Do you think you can fall in love with me?

7. Does this make my butt look big?

8. Am I fat/ugly?

9. Do you have enough money to pay for the date?

10. How much money is in your bank account right now?

11. Why did you dump your last girlfriend?

12. How many people have you slept with?

13. Am I a better kisser than your ex?

14. Why are you dating me?

15. Do you think about your ex while you’re with me?

16. If you could change one thing about my body, what would it be?

17. How expensive of an engagement ring can you afford?

18. Am I more important than your mom?

19. Would you ditch all your friends to be with me?

20. Which one of my friends do you think is the hottest

21. Do you want to get married?

22. Do you want to have children?

23. What’s the most embarrassing thing that’s ever happened to you?

24. Do you have any STDs?

25. Do you like having a beer belly?

26. How long does it take you to get ready for a date?

27. How many girls’ numbers are in your phone?

28. Can I give you a makeover?

29. How much debt do you have?

30. Have you ever considered plastic surgery?

Personal Questions to Ask a Guy You Like

The purpose of personal questions to ask a guy is to increase your level of trust so that your relationship develops. Check out this list of some questions to ask someone you like to choose from.

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. How will you know when you’re ready to get married?

13. How do you feel about adopting a child?

14. If you could find out something about your future, what would you want to know?

15. What do you think the future holds for us and our relationship?

16. What are your financial goals?

17. What one thing do you most want to do before you die?

18. In what ways do you hope to grow and develop as a person in the next year?

19. What are two things you want to accomplish in the next year?

20. What would you like to change about your relationship with your parent(s) going forward?

21. 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)?

22. What age do you think is too old to still have children?

23. If you could be visited by someone from the future, who would it be (U.S. President, yourself)?

24. Would you stay with your spouse if her physical or mental qualities changed drastically (weight, lost a limb, experienced mental illness)?

25. What advice would you give your daughter when she starts dating?

26. 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?

27. If you could ask your parents one thing about their parenting or relationship with you as a child or adult, what would it be?

28. 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?

29. 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?

30. When you were a child, what fantasy did you dream of experiencing as an adult, that you still secretly wish you could experience?

31. Do you prefer someone cheer you up, join you in your misery, or leave you alone when you’re in a bad mood?

32. What are some unfavorable things people have said about you that you can now admit are or were true?

Personal Questions to Ask a Guy Crush

Do you know your lover well? or the guy that you’re seeing? To assess your knowledge about your guy and vice versa, we have listed some personal questions to ask a guy crush for you. Check them out!

1. Do you think double texting is a big deal?

2. What’s the most embarrassing thing you’ve ever done to get a crush’s attention?

3. When did you have your first kiss?

4. Do you believe in astrology? Does your sign fit you?

5. What’s the most spontaneous thing you’ve ever done?

6. If you go to a restaurant and have terrible service, is it ever OK not to tip?

7. Have you ever cheated on your S.O.?

8. Have you ever been cheated on?

9. What’s your biggest regret?

10. What’s your dream date night?

11. How many S.O.s have you had?

12. Are you looking for a relationship?

13. What do you consider a red flag in a relationship?

14. What is your love language?

Personal Questions to Ask a Guy Over Text

It can be a little bit challenging to figure out what to text a guy you like. If you want to learn more about someone, try asking him one of these personal questions to ask a guy over text. Whether you’ve gone on a first date or not, you can still use them.

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 s#x 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. If you were married and your wife could no longer have s#x, what would you do? Would you leave?

9. Have you ever cheated on someone?

10. Would you leave your spouse if she cheated?

11. Have you ever had a one-night stand?

12. What would you do if you found out your romantic partner lied to you about something very essential to who you thought she was?

13. How do you feel about the legalization of marijuana?

14. Would you ever date a recovering addict?

15. Do you believe in the death penalty?

16. What would you do if you found out your spouse committed a crime?

17. 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?

18. What’s one thing you’d change about our relationship?

19. What’s something that I do that really bothers you, but you’re afraid to tell me, or haven’t told me yet?

20. 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)?

21. What’s something you’d like to ask me, but are afraid to ask?

22. Have you ever committed a crime or been arrested?

23. Have you ever been addicted to anything (food, gambling, s#x)?

24. What’s the cheapest date you’ve ever taken someone on?

25. Under or over (toilet paper hanging)?

26. If we were going to commit crimes together, what would they be?

27. If you could be a fly on the wall, whose wall would you be on?

28. What would you do if you had to go a week without your cell phone?

29. What would be the soundtrack for a movie about your life?

30. Do you have a nickname known only to your family/friends?

31. What’s something you do alone that you would be embarrassed to do in front of others?

32. What’s the funniest or craziest lie you’ve ever told to get out of doing something you didn’t want to do?

33. Have you ever had a crush on a relative or one of your parents’ friends?

34. What’s the most unprofessional thing you’ve ever done at work?

Personal Questions to Ask a Guy about His Past

Are there a few questions you should ask a guy to make sure you have an engaging discussion about his past? Use this collection of personal questions to ask a guy about his past to keep yourself informed about a guy’s history.

1. How many past relationships have you had?

2. How did you meet your ex?

3. Are you in touch with your ex? What’s your equation like?

4. Why did you break up?

5. How serious was the relationship?

6. Did you introduce your ex to your parents?

7. How long ago did you break up?

8. Are you sure you’re over your ex?

9. What is the most fun date you went on with your ex?

10. Do you still follow each other on social media?

Personal Questions to Ask a Guy in Truth or Dare

Good truth or dare questions are thought-provoking, and some of them can give you the same sense of excitement as accepting a challenge. In this category, we have compiled the most intriguing personal questions to ask a guy in truth or dare to know more about your guy.

1. What’s the last lie you told?

2. What was the most embarrassing thing you’ve ever done on a date?

3. Have you ever accidentally hit something (or someone!) with your car?

4. Name someone you’ve pretended to like but actually couldn’t stand.

5. What’s your most bizarre nickname?

6. What’s been your most physically painful experience?

7. What bridges are you glad that you burned?

8. What’s the craziest thing you’ve done on public transportation?

9. If you met a genie, what would your three wishes be?

10. If you could write anyone on Earth in for President of the United States, who would it be and why?

11. What’s the meanest thing you’ve ever said to someone else?

12. Who was your worst kiss ever?

13. What’s one thing you’d do if you knew there no consequences?

14. What’s the craziest thing you’ve done in front of a mirror?

15. What’s the meanest thing you’ve ever said about someone else?

16. What’s something you love to do with your friends that you’d never do in front of your partner?

17. Who are you most jealous of?

18. What do your favorite pajamas look like?

19. Have you ever faked sick to get out of a party?

20. Who’s the oldest person you’ve dated?

21. How many selfies do you take a day?

22. Meatloaf says he’d do anything for love, but he won’t do “that.” What’s your “that?”

23. How many times a week do you wear the same pants?

24. Would you date your high school crush today?

25. Where are you ticklish?

26. Do you believe in any superstitions? If so, which ones?

27. What’s one movie you’re embarrassed to admit you enjoy?

28. What’s your most embarrassing grooming habit?

29. When’s the last time you apologized? What for?

30. How do you really feel about the Twilight saga?

5 Tips for Choosing Personal Questions to Ask a Guy

The personal questions to ask a guy will help you learn new things about a guy, whether you’re just starting to know him or have been dating him for a long. The best part is that they’ll spark further inquiries and in-depth discussions.

There are many excellent personal questions to ask him from which you can branch out, but you should only select those that are completely appropriate for your situation. Here are 5 tips to choose best personal questions to ask a man.

1. Asking personal questions also gives the other person a platform to express themselves freely and honestly about issues that they might otherwise have kept to themselves. It’s beneficial and, in some ways, even therapeutic! But if he doesn’t feel comfortable discussing something, be passionate. Try to place him at ease through the questions as well, so your questions must not cross the red lines.

2. Even while you shouldn’t ask all of them in one day since that would be intense, asking these questions is a great place to start when you want to become more personal. So you should ask these questions at appropriate intervals to get optimum intimacy. 

3. These questions should be as informal as you can make it. However, the time must be right! By this, we mean that you wouldn’t inquire about a man’s personal life in the midst of a supermarket. Instead, when you’re curled up in bed, the lights are off, and the night is still young, you’re more likely to be in a good position to ask him personal questions.

4. You must also be willing to share personal information when it comes to the personal questions to ask a guy. In fact, introducing that question back to them by offering some information on the subject can be really effective.

5. Knowing that you can chat to someone about anything and everything is also quite satisfying. That’s actually pretty unique. Therefore, it would be wise to make these questions further entertaining. Remember that this should only serve as a starting point for you to come up with further personal questions you might ask a guy.

Final Thoughts on Personal Questions to Ask a Guy

It can be challenging to move beyond the standard questions that everyone asks when you want to know someone better. We’ve created this list of personal questions to ask a guy for that reason. They are excellent when you want to know a guy better on a deeper level.

You have a decent number of options without having too many to pick from because there are enough questions. Keep in mind to encourage him for more information as you are asking the questions.

Ask one of these personal questions to ask a guy the next time you’re alone with the guy you’re dating and see where the discussion leads. Remember to repay the favour by contributing your own response.

You may learn more about someone by asking them the aforementioned personal questions, which will help you build stronger trust. Spend a date night or weekend asking the special guy in your life several of these personal questions to ask a guy.

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