21+ Great Questions to Ask a Guy You Like

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.

In this post you will find following types of questions:

  • 21 Best of the Best Questions
  • 21 Questions to Know Him Better
  • 21 Questions to Make Him Open to You
  • 21 Cute Questions to Show Interest in Him
  • 21 Would You Rather Questions
  • 21 Funny Questions
  • 21 Kinky Questions

21 Best Questions for Hours-Long Conversations

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?”
21 Questions to Know Him Better

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 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?”
21 Questions to Make Him Open to You

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?”
21 Cute Questions to Show Interest in Him

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 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?”
21 Would You Rather Questions to Make Him Thinking

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?”
21 Funny Questions to Make Him Smile

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 shape shift, 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?”
21 Kinky Questions to Create a Sexual Spark

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 a sex in 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?”

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