So there is a guy you know and like a lot, but you do not know what questions you should ask him to learn more about his personality.

No matter if he is your co-worker, classmate, or a guy you often stumble into in the grocery store, following lists of various questions will help you to engage in hours-long conversations.

Best Questions For Hours-Long Conversations

Choose From Examples Below

1. “Do you believe in karma? Why?”

2. “How did you and your best friend meet?”

3. “Are you superstitious? If so, what are you most superstitious about? Why?”

4. “Are you spiritual or religious in any way? If so, how?”

5. “What are your life and career goals in 5, 10 and 15 years?”

6. “Do you believe it is vital to everyday life to know what is happening in the world around you?”

7. “What one dead person would you most like to have dinner with if it were possible?”

8. “Who is a non-politician you wish would run for office? Why?”

9. “What fictional character reminds you most of yourself?”

10. “If money and career were no object, where in the world would you choose to live?”

11. “If you were told you only had one week left to live, what would you do?”

12. “What is your funniest childhood memory?”

13. “What’s the first thing you’d do if you were the opposite sex for one day?”

14. “What is your most favorite time of the year? Why?”

15. “What one thing would you be most disappointed if you never got to experience it?”

16. “If you could have been a child prodigy what would you have wanted to be skilled at?”

17. “What superpower would you want to have for one day? What would you do with it?”

18. “If you could go back in time, what is one piece of advice you would give your younger self?”

19. “If you could eat one meal for the rest of your life, what would it be?”

20. “Who knows you the best? What best stories have you experienced together?”

21. “What is something you used to do as a child that you wish you could still do?”

22. “Do you believe that everything happens for a reason?”

23. “Have you ever sat by the phone all night waiting for someone to call?”

24. “Who’s your favorite protagonist from an animated movie?”

25. “What view would you most like to have out of your window?”

26. “Do you sleep with a stuffed toy? What is it?”

27. “What’s the habit you hate the most in a girlfriend?”

28. “Have you ever hated loving someone?”

29. “Do you consider it more important to be liked or respected? Why?”

30. “What product has greatly exceeded your expectations?”

Questions To Know Him Better

Choose From Examples Below

1. “How would you describe yourself in three words?”

2. “What is your favorite food you could not live without?”

3. “What would you do if you won the lottery?”

4. “How would you describe yourself, as an introvert or an extrovert?”

5. “What is your favorite sport to watch/play?”

6. “If someone told you that you could give one person a present and your budget was unlimited – what present would you get and for whom?”

7. “Are you more of a night owl or a morning person?”

8. “Do you think it’s important to stay up to date with the news?”

9. “What after-school activities did you do in high school?”

10. “What was the greatest television show of all time?”

11. “What “most likely to” superlative would you be most honored to receive?”

12. “What story do your friends still give you crap about?”

13. “What is the best present you’ve ever received?”

14. “Where would you prefer to live: beach, city or country?”

15. “What’s been your favorite age so far?”

16. “Which is better – a novel or a movie?”

17. “What is one thing you will never do again?”

18. “What’s your most listened-to song?”

19. “What are your favorite hobbies?”

20. “Have you ever been arrested or contracted any dangerous diseases?”

21. “What was your favorite TV show as a kid?”

22. “What is something you’ve never done that you’ve always wanted to do?”

23. “What is your biggest fear?”

24. “Do you easily accept compliments? Or do you hate compliments?”

25. “Are you a troublemaker?”

26. “How seriously do you take horoscopes?”

27. “What would you grab if your house was on fire?”

28. “What’s one place you really want to travel to?”

29. “If you were a girl for a day, what would be the first thing you do?”

30. “What makes you really irritated? Especially something other people do that irritates you!”

Questions To Make Him Open To You

Choose From Examples Below

1. “What is your biggest regret in life so far?”

2. “What’s the last book you read that you simply could not put down until you finished?”

3. “What would your parents be surprised to learn about you?”

4. “What happened the time in your life when you were the most nervous to do something?”

5. “If there is any place in the world that you could go, where would it be and why?”

6. “What is your most bizarre pet peeve?”

7. “What happened the last time you cried?”

8. “What is the weirdest quirk your family has?”

9. “What is the scariest experience you have ever had?”

10. “What about yourself do you find the most pride in?”

11. “What is the most embarrassing thing that has happened to you?”

12. “Is there anything you’ve done in the past that you can’t forgive yourself for?”

13. “Do you still have feelings for someone in your past?”

14. “What are your three weaknesses?”

15. “What time in your past would you love to return to?”

16. “What is the craziest thing that you have ever done in your life?”

17. “What is your dream date?”

18. “Which is more logical to follow – your heart or your head?”

19. “What was the worst age you’ve been so far?”

20. “If you could choose one superpower, what would it be and why?”

21. “What is on your bucket list?”

22. “What is the happiest memory of your childhood?”

23. “What is your ultimate goal in life?”

24. “Who has influenced you the most in your life?”

25. “What is your biggest fear?”

26. “Are you close with your family?”

27. “What is the one place in the world you wish you lived in?”

28. “What is the worst thing about dating?”

29. “What is the one movie that influenced your life the most?”

30. “What is the most embarrassing moment of your life?”

Cute Questions To Show Interest In Him

Choose From Examples Below

1. “What makes you smile?”

2. “What do you notice first when you first meet a girl?”

3. “What was your first kiss like and whom did you give it?”

4. “What is your definition of intimate?”

5. “What is the weirdest thing you find attractive in a person?”

6. “What is your favorite romantic activity?”

7. “What is your greatest fear?”

8. “Who was that first girl you had a crush on?”

9. “What do you believe I am thinking right now?”

10. “What was your worst kiss?”

11. “What was the scariest moment in your life?”

12. “What makes you nervous?”

13. “What is the nicest thing anybody has said, or you believe they would say, about you?”

14. “What fictional character do you have the biggest crush on?”

15. “What was your most embarrassing look?”

16. “What qualities do you want in a girlfriend?”

17. “Do you think of yourself as being naughty or nice?”

18. “What’s your favorite way to spend a rainy day?”

19. “Would you ever visit a nude beach?”

20. “If we were dating, how would you celebrate our first one year anniversary?”

21. “Would you like to hang out with me more often?”

22. “What kinds of things really make you laugh?”

23. “What was your major?”

24. “Do you have any pet peeves?”

25. “What do you do, and how long have you been doing it?”

26. “What’s your biggest goal in life right now?”

27. “Are you a cat person or a dog person?”

28. “Who has been the biggest influence in your life?”

29. “Have you figured out your calling in life? What is it?”

30. “What type of music are you into?”

Questions To Know His Family & Friends

Choose From Examples Below

1. “How is your relationship with your mom?”

2. “Do you have any brothers or sisters?”

3. “What do you value the most when it comes to friendship?”

4. “How is your relationship with your father?”

5. “How often do you talk with your parents?”

6. “What’s your best memory with your father/mother/sibling in it?”

7. “What jobs did your grandparents do?”

8. “Who do you think knows you the best?”

9. “Where is your bloodline originally from?”

10. “How regularly do you see your best friends?”

11. “How did you and your best friend meet?”

12. “Tell me about a funny family story.”

13. “Which relative are you emotionally closest to?”

14. “Where did your parents meet?”

15. “Who is the wisest person in the family?”

16. “If you had to choose, what family member would you kill off and why?”

17. “Tell me about a family member you are really proud of.”

18. “Who’s your best friend?”

19. “Where is your bloodline originally from?”

20. “How did you and your best friend meet?”

21. “Who is the kindest person in your family?”

22. “What’s the most immature thing your parents do?”

23. “Who is the wisest member of your family?”

24. “What’s the weirdest tradition your family has?”

25. “What bad thing did you do as a kid that your parents never found about”

26. “What’s your “and then it got worse” family story?”

27. “Do you have any relative in jail?”

28. “Do you have any famous relatives?”

29. “How close are you to your family?”

30. “What jobs do your parents do?”

Would You Rather Questions To Make Him Think

Choose From Examples Below

1. “Would you rather be twice as smart or twice as happy?”

2. “Would you rather be a good guy or a bad guy in a comic or a movie?”

3. “Would you rather go for a beach vacation or European vacation?”

4. “Would you rather live in a large house in the suburbs, or a tiny apartment in the city with an excellent view?”

5. “Would you rather apologize or ask for a permission?”

6. “Would you rather have unlimited love or unlimited money?”

7. “Would you rather be hairy all over your body or completely bald?”

8. “Would you rather get rid of your sadness or your anger?”

9. “Would you rather forget who you were or who everyone else was?”

10. “Would you rather be invisible or be super strong?”

11. “Would you rather have one wish fulfilled immediately, or three wishes fulfilled in 10 years?”

12. “Would you rather be able to stop time or be able to fly?”

13. “Would you rather give up your computer and phone or your car and bike?”

14. “Would you rather date a girl who surprises you or a girl who is blunt?”

15. “Would you rather give up your favorite food or give up sex for six months?”

16. “Would you rather date a good kisser or a good lover?”

17. “Would you rather be purely physical or make a commitment?”

18. “Would you rather make the first move or wait for her to do it?”

19. “Would you rather French kiss me in front of my parents or see your parents French kissing?”

20. “Would you rather consider dating a hot girlfriend or one with a winning personality irrespective of physical attraction?”

21. “Would you rather have sex while someone attractive is watching you, or would you want to watch someone have sex in front of you?”

22. “Would you rather be in a bad relationship for the rest of your life or have no SO for the rest of your life?”

23. “Would you rather take a vow of celibacy or take a vow of silence?”

24. “Would you rather lose the ability to hear or lose the ability to walk?”

25. “Would you rather spend $5,000 on traveling or on a physical item like a TV?”

26. “Would you rather stay in or go out for a date?”

27. “Would you rather not shower for a week or not brush your teeth for a week?”

28. “Would you rather ask for help or figure it out yourself?”

29. “Would you rather go to a fancy, expensive restaurant or a cheaper relaxed atmosphere where the food is equally good?”

30. “Would you rather work a morally questionable job that makes a lot of money or a job that helps a lot of people but doesn’t make much money?”

Thought Provoking Deep Questions That Will Take His Breath Away

Choose From Examples Below

1. “What are the things that stand between you and complete happiness?”

2. “When someone sees your name on caller ID, what thoughts and feelings do you want them to have?”

3. “If you were going to die at midnight, what would you be doing at 11:45 pm?”

4. “Standing at the gates of heaven, and God asks you “Why should I let you in?” What do you reply?”

5. “If you woke up tomorrow as an animal, what animal would you choose to be?”

6. “If you could go back in time, once, and change a single thing – what would it be?”

7. “Would your life be better or worse, if you knew the time and place where you would die?”

8. “If you could start over, what would you do differently?”

9. “What habits are holding you back from success?”

10. “What have you done to pursue your dreams lately? How about today?”

11. “What is one dream you think you’ll pursue relentlessly for the rest of your life?”

12. “Do you think human morality is learned or innate?”

13. “Do you think the present is better than 50 years ago? Why?”

14. “If science makes it possible to predict which people will be more likely to commit crimes, should the highest risk individuals be jailed or killed before they can commit crimes?”

15. “What are the most common roadblocks that stop people from achieving their dreams?”

16. “What would you change about your life if you knew you would never die?”

17. “What would you have to see to cry tears of joy?”

18. “What makes a person truly evil? Are they born that way or did their environment make them that way?”

19. “How regularly do you see your best friends?”

20. “What will people say at your funeral?”

21. “What would you do differently if you could turn back time?”

22. “If you could watch everything that happened in your life until now, would you enjoy it?”

23. “What is the hardest lesson you had to learn in life?”

24. “What would you do differently if you knew that no one was judging you?”

25. “Do you believe everything happens for a reason, or do we just find reasons after things happen?”

26. “How do you celebrate the things you do have in your life?”

27. “In your life, what has been the biggest blessing in disguise?”

28. “When you’re 90 years old, what will matter most to you in the world?”

29. “If you could write a note to your younger self, what would you say in only three words?”

30. “How much is a human life worth and are some lives worth more than others?”

Flirty Questions To Make Him Fall For You

Choose From Examples Below

1. “Which is the first region your eyes would wander to if you were to ever see me naked?”

2. “Have you ever decided to kiss or make out with a girl just because you were horny?”

3. “What is the naughtiest moment in your school days that you can remember?”

4. “If I ask you to ask me to do something naughty what would you prefer the most from me?”

5. “Have you ever had a dream about being a gay?”

6. “What do you prefer on girls; thongs or panties?”

7. “While you are kissing, what types of other things you prefer to be done simultaneously?”

8. “Where you do like being touched the most?”

9. “What is your wildest sexual secret that you want to indulge in at least once in your lifetime?”

10. “Have you ever had an unexpected orgasm?”

11. “What’s your favorite thing to do with a girl?”

12. “What kind of underwear are you wearing right now?”

13. “If we only had twenty-four hours together, what do you think we’d do?”

14. “Are you a troublemaker?”

15. “What tricks do you use to turn a girl on?”

16. “Where’s your favorite place to get a butterfly kiss?”

17. “What do you find attractive in a girl?”

18. “What’s more romantic, or sexy: cooking for someone or dancing with someone?”

19. “What do you think is the number one blunder girls make when flirting with or hitting on man?”

20. “What do you think is one thing all girls should do when dating?”

21. “Do you believe in love at first sight?”

22. “Have you ever been on a date that totally blew your mind? Like one of those movie moments?”

23. “What’s your weakness/soft-spot in a girl?”

24. “If we only had twenty-four hours together, what do you think we’d do?”

25. “If you had X-Ray vision glasses, would you use them to see under the clothes?”

26. “What do you wear to bed- if anything?”

27. “Do you find yourself more drawn to brains or looks?”

28. “How far can you go on our 3rd date?”

29. “Do you prefer cuddling or making out?”

30. “What would be your perfect romantic getaway?”

Funny Questions To Make Him Smile

Choose From Examples Below

1. “Which animal do you consider to be the sexiest?”

2. “What nickname would you give me based off my personality or a body part?”

3. “Which animal do you think is your spirit animal?”

4. “What would you do if you could be invisible for one whole day?”

5. “If you could shapeshift, which shape would you try to take?”

6. “What would people hear if they could read your mind?”

7. “Would you study Elven or Klingon language?”

8. “What’s your favorite comedy movie?”

9. “What’s your favorite joke?”

10. “If you could see the future, what would you hope to see yourself doing in 5 years?”

11. “If your life was a movie, which actor would play you?”

12. “Who is your funniest friend?”

13. “If you could read minds, whose would you want to read and when?”

14. “Have you ever been caught naked by someone?”

15. “What is your favorite childhood toy?”

16. “Would you spit in a customer’s food if you were the waiter and they had been rude to you?”

17. “What is the weirdest nickname people call you?”

18. “What is the worst thing that somebody has walked in on you doing?”

19. “What’s your favorite funny pickup line?”

20. “If you could commit any crime and get away with it, what would it be?”

21. “Which weapon would you pick for your zombie apocalypse survival?”

22. “Which habit are you proudest of breaking?”

23. “What’s your favorite joke?”

24. “What was the strangest punishment your parents ever gave you?”

25. “What’s the worst thing someone has walked in on you doing?”

26. “What is the ugliest thing you own?”

27. “What kind of things really makes you laugh?”

28. “What would you do if you could be invisible for one day?”

29. “Have you ever had a crush on an animated character?”

30. “What’s the weirdest nickname you’ve ever had?”

Kinky Questions To Create A Sexual Spark

Choose From Examples Below

1. “What’s the kinkiest thing you’ve ever done?”

2. “Do you like to be spanked?”

3. “Where do you like to kiss a woman?”

4. “If you could sleep with one person, who would it be?”

5. “Have you ever had sex in a shower? Did you like it?”

6. “Do you like morning sex?”

7. “Do you prefer women in lingerie?”

8. “What’s your darkest sexual fantasy?”

9. “Where is your favorite place to have sex?”

10. “Where was the worst place you ever had sex?”

11. “Do you like playing with sex toys?”

12. “Do you enjoy food with sex?”

13. “What are your secret turn-on places?”

14. “Do you like being tied up?”

15. “If you could only have one type of sex for the rest of your life, what would you choose: oral, anal or regular?”

16. “Have you ever had phone sex? Did you like it?”

17. “What are your craziest and most favorite sex positions?”

18. “Have you ever woken the neighbors because you were so loud in the bedroom?”

19. “Have you ever had sex in a public place and got caught?”

20. “Have you ever woken up beside someone you regretted sleeping with?”

21. “Would you be angry if you saw me making out with a really hot girl?”

22. “Have you ever been caught having sex?”

23. “Does a massage make you horny?”

24. “Which celebrity would you sleep with in a blink of an eye?”

25. “Who’s the one person in this world you wish you could fuck?”

26. “Will you cheat on your girlfriend with an ex whom you still have strong sexual chemistry with?”

27. “Do you like it rough or gentle?”

28. “Where was the craziest place you ever had sex?”

29. “What’s the dirtiest thing you’ve ever sexted someone?”

30. “How often do you masturbate?”

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