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512 Personal Questions to Ask a Guy to Improve an Existing Relationship

We’re glad you’re here for one of the most intriguing collections of personal questions to ask a guy.

You need to ask a guy incredibly in-depth personal questions since it is hard to know what a guy is thinking about or what his intentions are toward you unless you have a mind-reading talent.

To receive the outcomes you want, you must ask the appropriate questions at the right time, though.

There are personal questions to ask a guy that should be asked at the right moments, regardless of whether you’re looking to develop an already-existing relationship, determine a guy’s intentions towards you, or simply get to know him.

Some personal questions to ask a guy are appropriate for the initial few days of a potential partnership, while others are better saved for later in a relationship.

We have compiled a comprehensive list of some incredibly deep personal questions to ask a guy in case you’re unsure of what kind of questions to ask or when to ask them.

Most Personal Questions to Ask a Guy

Do you require a list of inquiries to make sure your talk with a guy is fruitful? Make use of this list of the most personal questions to ask a guy to keep things interesting.

1. What has been the best day of your life so far?

2. Do you have a bucket list? What is on it?

3. Do you have any really embarrassing stories?

4. What’s your favorite food? What would your death-row meal be?

5. Where is your favorite restaurant?

6. What’s the best place you have ever traveled to?

7. Do you have a good or bad relationship with your parents?

8. Do you have siblings? Do you get along with them?

9. Who are your best friends?

10. What’s your idea of the best day ever?

11. What are your political views?

12. Who’s your favorite person in the world?

13. How would you describe yourself?

14. What kind of music do you like?

15. Do you like going to the cinema or theatre?

16. What makes you your happiest?

17. What makes you feel sad?

18. Do you believe in religion? Or what do you believe in? Do you follow any faith in particular?

19. What are your goals in life?

20. What are some of the rules that you choose to live by?

21. What do you really want to do? Or are you already doing it?

22. Where did you grow up?

23. Do you play any sports? Do you like sports?

24. Are you a stay at home or go out and party kind of person?

25. What’s your favorite book?

26. What’s your favorite film?

27. What do you love most about yourself?

28. What do you wish you could be better at?

29. What’s your idea of a really amazing date?

30. What’s your type?

Super Personal Questions to Ask a Guy

We’ll obtain valuable replies more quickly if we ask the correct questions to get to know someone. Utilize these super personal questions to ask a guy to know more about him.

1. What’s your favorite song?

2. Have you ever met anyone famous?

3. Would you like to be famous?

4. Do you prefer the countryside or the city?

5. Do you like the beach?

6. Are you scared of anything?

7. Have you ever done extreme sports?

8. Do you have any tattoos? If so, what do you have and where is it?

9. If you won or inherited a lot of money, what would you do?

10. What’s your ideal home?

11. What’s your favorite thing to cook? Or, what is your signature dish?

12. What’s the craziest thing you have ever done?

13. Do you wish you had done things differently in the past?

14. Do you believe in the after-life?

15. Do you believe in ghosts?

16. What’s your all-time favorite car and why?

17. If could, would you change anything about yourself?

18. Have you ever made any enemies?

19. What’s something you have never told anyone before?

20. What’s your dream destination?

21. Do you like animals?

22. Would you ever get a dog or a cat?

23. Have you ever been a bully?

24. What’s the coolest band you have ever seen live?

25. What do you look for in a partner?

26. Can you ride a motorbike? Do you want to get one?

27. When you were a child, what did you really want to do for a job when you were older?

28. What was your biggest childhood dream?

29. What’s your favorite thing about me?

30. If you never had to work again, would you?

31. If you never had to worry about money, what would you do?

32. What is the craziest fact about yourself?

33. Do you have any hidden skills?

34. Do you want kids in the future?

35. What are your views on climate change?

Very Personal Questions to Ask a Guy

The amount of pleasure you can have with your male pals is unmatched. Oh, my goodness, if there is any naughtiness involved. Although you may be aware of their peculiar side, are you truly willing to look farther and reveal all of their actions? Here are some very personal questions to ask a guy that you should look into. ‎

1. Have you ever been skiing or done winter sports?

2. What do you want your life to be like in the new few years?

3. What was your favorite vacation you went on as a kid and why?

4. What were you most afraid of?

5. Have you ever got into trouble with the police?

6. What’s one of your favorite memories growing up?

7. Who did you look up to the most and why?

8. What was your favorite toy/book/movie/collectible and do you still have it?

9. Have you ever done anything illegal?

10. What do you think people think of you?

11. Do you believe in ghosts? Have you ever seen a ghost?

12. What’s your favorite thing to do in your free time?

13. What’s your best party trick? Show it to me.

14. If you could have a superpower for one day, what would it be?

15. Did you prefer to spend time with one friend or a big group of people?

16. What are your strengths and weaknesses?

17. How important was it that you go to family gatherings and stay close to family members?

18. Do you have any bad habits?

19. Do you have any regrets?

20. Are you creative or academic?

21. What did you study?

Really Personal Questions to Ask a Guy

You should include both amusing and revealing questions in your compilation of things to ask a guy. When they feel cornered, they could build a wall and isolate themselves. So, here are some really personal questions to ask a guy.

1. What was the best gift that you ever gave someone?

2. Was there ever a time when you felt excited to go somewhere, only to have the plans canceled?

3. What was the most hurtful thing that anyone has ever told you?

4. If you would come face to face with someone who hurt you in the past, what would you tell them?

5. Did you have a lot of the same habits and behaviors or have you changed a lot?

6. Did you regularly attend religious services as a child? If so, who took you? Parents? Grandparents? Another relative?

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

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

9. What do you think is the worst feeling that anyone could possibly feel?

10. What have you learned from previous encounters with toxic people?

11. How would you describe a toxic person?

12. If someone significant to you – like a parent or sibling – were too toxic to be around, what would you do and how would you deal with it?

13. What’s the worst thing a person can be?

14. 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?

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

16. Do you think that a person’s past defines their future?

17. When would you consider yourself to be truly successful or accomplished?

18. What’s more important – stability or excitement?

19. Is there a memory you have that you hope you’ll never forget?

20. What’s your best quality?

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

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

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

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

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

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

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

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

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

30. Do you think that people can get along even when they have absolutely nothing in common?

31. If you had to live in a remote location for 5 months and you’re only allowed to bring three things from your bedroom, what would they be and why?

32. If you discovered today that you were adopted, what would your reaction be?

33. Is it always important to be honest? Or are there some instances when honesty is only a second priority?

34. Is there any part of your life that you feel needs improvement? What is it and how do you think you can work to achieve that improvement?

Deep Personal Questions to Ask a Guy

These are some significant yet straightforward deep personal questions to ask a guy. They are open-ended and provide an invitation to share. Some of these may be used as text inquiries, but if you want to start a meaningful conversation, we advise seeing the guy in person.

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

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

3. Are you happy with the person you are?

4. Do you ever feel depressed?

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

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

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

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

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

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

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

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

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

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

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

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

17. 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?

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

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

20. Were you ever in trouble with the law?

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

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

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

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

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

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

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

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

29. Are you a religious person?

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

31. Do you consider yourself smarter than most people?

Good Personal Questions to Ask a Guy

If you’re looking for new ways to connect with guys, you’ll have a lot of fun with these good personal questions to ask a guy. Additionally, you’ll reach a completely new level of intimacy since you’ll be learning so much about one another.

1. If you found out that you’re dying in a month’s time, what would you do with the time you had left?

2. What do you consider your biggest accomplishment and why?

3. If you could be famous for a day, what would you do?

4. If you could have a million dollars fall into your lap right now, but you can’t spend any of it on yourself, how would you spend the money?

5. What’s one thing that you think you’re really good at that other people might typically have trouble with?

6. What’s one secret that you can share with me?

7. What’s the biggest lesson you’ve ever learned in life?

8. If you could change anything about your childhood, what would it be and why?

9. What’s something that you feel very passionately about?

10. What would you want to be written on your tombstone?

11. If you would become a parent, what’s something that your parents used to do to you that you would never do to your own child?

12. What’s your biggest insecurity?

13. If you could go back in time and change one thing, what would it be and why?

14. If you could sit down and have a meal with someone – anyone whether dead or alive – who would it be and why?

15. What’s a life lesson that you think would make the world a better place if everyone learned it?

16. If someone told you that you would lose all of your earthly possessions tomorrow and you wouldn’t have anywhere to live, what would you do?

17. What’s something that someone might do to you that you could never forgive?

18. What’s your biggest character flaw?

19. If there’s one thing you could change about your personality, what would it be and why?

20. What do you think is the secret to happiness?

21. How can a person become truly successful?

22. What is the measurement of a person’s success?

23. What’s your biggest fear and why?

24. Do you believe in the saying “forgive and forget?”

25. What is a bad habit you have that you struggle to eliminate from your life?

26. If you could take a single photograph to represent your whole life, what would it be a picture of and why?

27. What’s something that most people have but rarely appreciate?

28. What’s something that you love but feel embarrassed about?

29. Do you think that time does heal all wounds?

30. Do you think that youth is an advantage, or are people of all ages capable of doing the same things?

31. If you could dive into a pool of anything right now, what would it be a pool of?

Dirty Personal Questions to Ask a Guy

Understanding a guy’s thoughts is always intriguing. And how much pleasure is it to learn how dirty their thinking is? The following are some dirty personal questions to ask a guy you may use to find out a guy’s secrets.

1. What turns you on?

2. Is there anywhere on your body in particular that you love being touched or played with?

3. Have you ever had shower s#x?

4. Do you like s#xting?

5. Have you ever been to a strip club?

6. Have you ever had s#x outdoors?

7. What’s the craziest place you have ever had s#x?

8. What’s the craziest place you have ever masturbated?

9. Do you like receiving nudes?

10. Would you ever send nudes?

11. How many times a week is your ideal number to have s#x?

12. What is a definite turn off for you?

13. Do you have any fantasies?

14. Do you have any fetishes? What are they?

15. How often do you masturbate?

16. Are you the kind of guy that likes to be in control or likes to be controlled in the bedroom?

17. Have you ever slept with someone on the first date?

18. How many people have you slept with in total?

19. What do you think is the hottest thing a woman can do?

20. What do you sleep in?

21. Have you ever had a threesome? What do you think about them?

22. What kind of porn do you watch? Would you like it if we watched it together?

23. How good is your stamina in the bedroom?

24. What’s the best s#x you have ever had and why was it so good?

25. What’s the worst s#xual experience you have ever had and why was it so bad?

26. Do you prefer shaved or not on a woman?

27. Have you ever experimented with someone of the same s#x?

28. What would be your dream s#x situation?

29. What’s your favorite – ass or tits?

30. What would you love to see me wearing?

31. Do you like it when a woman tells you she fingers herself?

32. Have you ever done anal with anyone?

33. What’s your favorite outfit for a woman to be wearing? Would you like to see me wearing that?

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 to keep him blushing if you want to flirt but aren’t sure how to make your intentions clear.

1. Do you think having s#x turns into making love when you are in love with someone?

2. Do you want to be the best version of yourself when I am around you?

3. Would you be happy to wear sweats and watch films with me all night rather than go out to a fancy dinner?

4. What do you think about love?

5. Do you think that we all have soul mates?

6. When was the first time you fell in love?

7. Do you believe in marriage?

8. Do you want to get married one day?

9. Do you think marriage is necessary before children?

10. What would be your dream marriage?

11. How long do you think you should be in a relationship before you get engaged and married?

12. Do you want children at some point in the future?

13. What do you visualize for yourself in the future? Do you want to live in a particular kind of house or have a big family?

14. Do you think love is the same as lust?

15. Do you like to cuddle?

16. Is the physical part of a relationship important to you?

17. Have you ever kissed someone in the rain before?

18. Do you like public displays of affection?

19. What do you think is the most important thing in a relationship?

20. How would you describe the relationship between us?

21. Have you ever dreamt about me?

22. Do you see a future between us? If you do, what is it like?

23. Have you ever written a love song or a love letter? Would you?

24. Do you believe that love is the most important thing in the world?

25. What do you want to call your children?

26. Do you think you would be a good father?

27. Would you ever cheat on someone?

28. Have you ever been cheated on before?

29. Do you have any relationship deal breakers?

30. What are you looking for in a partner?

31. Is love about looks or personality to you?

32. Do you ever miss me when I am not around?

33. What do you think is the most romantic thing ever?

Weird Personal Questions to Ask a Guy

Let’s now go through a few weird personal questions to ask a guy. You won’t be able to open your eyes to blink after hearing his comments, I can assure you of that.

1. What would be the funniest idea of a date for you?

2. What geeky thing makes you laugh?

3. Who would play you if your life was portrayed in a film?

4. When was the last time you danced around in the shower whilst singing your all-time favorite love ballad? Come on, I know you do it!

5. Have you ever been caught in your birthday suit?

6. What’s the best joke you have ever said?

7. What’s the most embarrassing story to ever happen to you?

8. What is the worst outfit you have ever worn and where is the photographic evidence?

9. What’s the weirdest thing you have ever seen someone do when you were stuck in a traffic jam?

10. Were you ever called any funny names as a kid?

11. What’s the funniest and worst name you could ever think of giving a child?

12. How many times do you change your boxers in a week?

13. How many times do you fart in a day?

14. Have you ever been caught masturbating?

15. At what age did you have your first wet dream?

16. Have you ever swallowed your own vomit?

17. Will you kiss another guy for 100,000 Dollars?

18. Do you pee on yourself when you shower?

19. Will you marry me?

20. What is the most embarrassing thing you have ever done?

21. Have you ever lusted after a friend’s girlfriend?

22. What’s the funniest thing you have ever done when you’ve been drunk?

23. What would a woman look like if she was a copy of you?

24. If you were arrested, what would your friends think you had done?

25. What is the funniest memory that we have together?

26. Would you get excited if all of a sudden you woke up in a woman’s body? What would you do first?

27. If you were a porn star or a stripper, what would your name be?

28. What’s the most ridiculous way that you have ever hurt yourself?

29. Would you rather urinate Gold or defecate cash?

30. How many times a day do you think about s#x?

31. How healthy do you consider masturbation to be?

32. What is the stupidest thing you have ever said to someone?

33. How many plates of food can you consume in a sitting?

34. What insect are you most afraid of?

35. Have you ever walked in on a couple having s#x?

36. How many lies do you tell in a day?

37. Guess how many guys I have kissed

38. Are you in love with me?

39. Have you ever thought of another person other than your partner when having s#x?

Serious Personal Questions to Ask a Guy

We all struggle with the question of what to discuss with a guy at first, so we get to know them better. Check out this list of important serious personal questions to ask a guy to strengthen your relationship if you’re stumped.

1. What does your dream house look like, and where is it?

2. Have you ever lost a loved one? If so, who was it?

3. What is the hardest thing you have ever been through?

4. How do you deal with challenges?

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

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

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

8. Are you an introvert or extrovert?

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

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

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

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

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

14. What is your favorite food/meal?

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

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

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

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

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

20. What is your favorite ice cream flavor?

21. How do you relax when you are stressed?

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

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

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

25. What motivates or inspires you?

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

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

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

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

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

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

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

Embarrassing Personal Questions to Ask a Guy

Establish a friendship with a person if you wish to learn some embarrassing things about him. They don’t talk to just anybody, and they never do if the topic is embarrassing. You may use these embarrassing personal questions to ask a guy.

1. When was the last time you cried?

2. Guess how many guys I’ve slept with?

3. Have you ever killed or seriously injured anyone?

4. Have you ever been arrested?

5. Would you ever watch taboo pornography?

6. If you wanted to kill me, how would you do it?

7. If you held a world record, what would it likely be for?

8. If you could be any insect, what would you be?

9. What location in the world are you least likely to visit?

10. What’s the one app you couldn’t live without?

11. Could you survive without your cell phone?

12. Would you let me ______ (fill in the blank with an explicit and weird request)?

13. Have you ever found a child attractive?

14. Do you think teen girls are hot?

15. Guess how old I am?

16. How much do you think I weigh?

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

18. Are you sure you’re not gay?

19. Do you like having a beer belly?

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

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

22. Can I give you a makeover?

23. How much debt do you have?

24. Have you ever considered plastic surgery?

Personal Questions to Ask a Guy You Like

Okay, I understand it might be challenging to strike up a personal conversation with a guy, especially if you like him. Since it might damage your connection with him and your reputation as a whole, you don’t want to look to be going over the line. But guess what? You can take a chance. If you want to use questions to ask someone you like, here are some suggestions. ‎

1. What was your longest relationship?

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

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

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

5. What cause are you most passionate about?

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

7. Who is your favorite person, and why?

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

9. What was your major in college?

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

11. What is your funniest pick-up line?

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

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

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

15. What is your greatest strength?

16. What is your biggest weakness?

17. Do you ever have road rage?

18. Are you a morning or a night person?

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

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

21. What is your favorite color?

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

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

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

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

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

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

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

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

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

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

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

33. What is your love language? Have you read the book?

Personal Questions to Ask a Guy Crush

There will always be new information about your crush to learn. Finding out about your crush is vital when you are in a new relationship. These personal questions to ask a guy crush will keep the conversation going, stimulate his interest, and give you additional insight into what makes your crush tick. ‎

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

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

3. 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?

4. What do you want your legacy to be?

5. Do you think couples should share passwords with each other?

6. Do you think men and women can just be friends?

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

8. How do you feel about adopting a child?

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

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

11. How would you describe your sense of humor?

12. Who’s your favorite comedian?

13. What’s your favorite comedy movie and TV show?

14. Have you ever played a prank or practical joke on someone? If yes, what was it?

15. Is there a commercial or chick flick that makes you cry?

16. If your spouse got a s#x change operation, would you stay or leave?

17. Have you ever had s#x in a public place?

18. What’s your best s#xual skill when it comes to giving a woman an orgasm (oral, hands, penetration, other)?

19. Have you ever had a three-some?

20. Have you ever gone to a nude beach? If not, would you?

21. When you’re home alone, do you walk around naked?

22. How do you feel about PDA (public displays of affection)?

23. Do you watch porn?

24. Are you more of a giver or receiver in the bedroom?

25. Have you ever gotten caught having s#x?

26. If I showed up at your job butt naked under my trench coat, what would you do?

27. Do you have a favorite stripper move, or a move you’d want to see a stripper or woman perform?

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

29. When did you lose your virginity?

30. Have you ever had someone play a funny prank or practical joke on you? If yes, what happened?

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

32. Under or over (toilet paper hanging)?

Personal Questions to Ask a Guy Over Text

The hardest part of texting a guy is usually getting the conversation going in the right direction. You may get started by using the personal questions to ask a guy over text. ‎

1. What is your favorite song, and why?

2. What is your favorite type of music?

3. What is the last concert or show you went to, and did you enjoy it?

4. What is your favorite sport, and why?

5. Do you play any sports? If so, which one do you play?

6. Do you play an instrument? If so, which one do you play?

7. Do you have a tattoo? What is it, and is there a meaning behind it?

8. If you were to get a tattoo right now, what would it be, and why?

9. Do you prefer girls with or without tattoos?

10. Do you prefer girls with or without piercings?

11. What is your favorite question to ask a woman on a first date? Why is it your favorite question?

12. What is your favorite movie, and why?

13. What is your favorite book, and why?

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?

Personal Questions to Ask a Guy about His Past

It’s probable that your partner has had his fair share of awkward incidents because you don’t see him very frequently, and this is the time to discuss them all. Use these personal questions to ask a guy about his past.

1. What’s your favorite childhood memory?

2. Who was your role model growing up?

3. Would your younger self be proud of where you are in life now?

4. What was your first impression of me when we met?

5. Have you ever lost a friend? If so, why?

6. What’s the biggest mistake you’ve ever made?

7. Do you have any weird habits that I don’t know about?

8. What’s your earliest memory?

9. Who was your first love, and why did you love them?

10. What was your first heartbreak, and what happened?

11. What’s been your greatest accomplishment in life?

12. What was the first concert you ever went to?

13. Who was your favorite childhood teacher?

14. Who was your first kiss with, and did you enjoy it?

15. If you could change one thing about yourself, would you?

16. Have you ever had a “life-changing” moment? If so, what was it?

17. If you had a childhood pet and they passed away, how did you handle that?

18. Have you ever given up on a dream? What was it?

19. How has your relationship with your parents changed?

20. What’s your proudest moment?

21. When have you felt the most challenged?

22. Who has been a big influence on you?

23. What’s the weirdest thing you believed as a kid?

24. If you could relive any moment in your life, would you? Which one?

25. What’s the hardest lesson you’ve ever had to learn?

26. What did you want to be when you grew up?

27. What advice would you give your younger self if you could?

28. Who were you closest to during your childhood?

29. What was your favorite place to spend time as a child?

30. What was the most challenging moment in your childhood?

31. What do you remember most about puberty?

32. What was your favorite TV show growing up?

33. Would you change anything about your past?

34. What are you most proud of about your past?

Personal Questions to Ask a Guy in Truth or Dare

Prepare a few personal questions to ask a guy in truth or dare before playing a game of truth or dare to make it work for you. These questions will come to your rescue if you find yourself stuck in the middle of a game because you are at a loss for words.

1. When was the last time you lied?

2. What’s your biggest regret?

3. If you had to only ever watch rom coms or only watch scary movies for the rest of your life, which would you choose and why?

4. Where is the weirdest place you’ve ever gone to the bathroom?

5. Have you ever ghosted on someone?

6. Which player would survive a zombie apocalypse and which would be the first to go?

7. Reveal all the details of your first kiss.

8. What excuse have you used before to get out plans?

9. What’s the longest you’ve ever slept?

10. What’s the shortest you’ve ever slept?

11. Read the last text you sent your best friend or significant other out loud.

12. What’s your biggest pet peeve?

13. What’s the most drunk you’ve ever been?

14. What five things would you bring to a deserted island?

15. Which is your favorite Hollywood Chris? Chris Evans, Chris Pratt, Chris Hemsworth or Chris Pine?

16. What’s the most embarrassing thing you ever did on a date?

17. What is the boldest pickup line you’ve ever used?

18. What celebrity do you think you most look like?

19. What’s the most embarrassing thing you’ve ever done?

20. What’s your biggest fear?

21. What’s your biggest fantasy?

22. Have you ever broken the law?

23. What’s something you’re glad your mum doesn’t know about you?

24. Have you ever cheated on someone?

25. What’s the worst thing you’ve ever done?

26. What’s a secret you’ve never told anyone?

27. Do you have a hidden talent?

28. Who was your first celebrity crush?

29. What are your thoughts on polyamory?

30. What’s the worst intimate experience you’ve ever had?

31. Have you ever cheated in an exam?

5 Tips for Choosing Personal Questions to Ask a Guy

In this part, we’ll provide you some helpful advice on how to pick the right personal questions to ask a guy.

1. To avoid coming across as pushy or overbearing, which can turn him off, choose the questions that are the most pertinent to him and plan out the sequence in which you will have to ask them.

2. Because it depends on the relationship between the parties, be careful not to offend your guy by using personal questions to ask him. To keep the conversation going, ask your guy what the inquiries should be about, or mix these intriguing questions with flirty, filthy, amusing, etc. ‎

3. Pay attention to yourself. And when I say “focused on yourself,” I mean putting your communication skills front and center. It will be beneficial to ask your guy these questions in the appropriate manner.

If you are good at communicating, you will come across as more confident, and confidence draws others to you. You’ll never run out of topics to talk about with him if you do this.

4. Make an effort to follow his speed. The discussion will end if you don’t keep up with its flow. The person at the other end of the table will never find it pleasurable.

You must first gauge his level of energy or the kind of conversation he is willing to have. Asking about his favorite movies while he’s looking for a romantic conversation is inappropriate.

Instead, enquire from him about instances in which he failed to see their goal or felt particularly exposed. ‎

5. Although you want to know him better, you don’t want to come out as desperate because that can make him lose interest.

If you’re unsure of how to strike that balance, look through the list of personal questions to ask a man, we provided, if you want to express your genuine interest in him.

These can help you deal with awkward silences and pauses and will force him to recognize your feelings. ‎

Final Thoughts on Personal Questions to Ask a Guy

You should test out these personal questions to ask a guy before taking your dating connection seriously.

When you are casually dating and haven’t decided on one particular person for a relationship, the qualities you are searching for in a guy may be very different from those you might seek in a long-term relationship or in a previous engagement.

Your first love interest or the guy you have the most fun with might not make the ideal partner.

It might be challenging to start a new relationship, particularly if you’ve just experienced heartbreak, but try not to allow your prior relationships deter you.

You must, however, also be certain that he is the appropriate man for you. Use these personal questions to ask a guy for that purpose. So be careful to set the stage with your questions so that the dialogue may continue.

Naturally, after exploring this list of personal questions to ask a guy, you’ll have much to speak about for the rest of the evening.

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