252 Questions to Ask a Guy You Like (For Texting and IRL)

Knowing what to say and ask to keep a conversation going with your crush is not easy. In this list, you’ll find plenty of questions you can try asking a guy you like the next time you two meet. Most of the questions work both for texting and real life.

Sections

  1. Get to know him questions
  2. Personal questions
  3. Deep questions
  4. Flirty questions
  5. Fun questions
  6. Questions for texting
  7. Random questions
  8. Weird questions
  9. Awkward questions

Questions to ask a guy you like to get to know him

These questions are a great way to start getting to know a guy you like. Getting to know the guy you like is important for you to understand if you are romantically compatible.

1. How old are you?
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2. What is your star sign?
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3. What is your favorite color?

4. What is your favorite music genre?
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5. What is your fashion taste?
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6. What three words best describe you?

7. Do you enjoy spending time alone?
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8. Do you consider yourself a gamer?
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9. What is your favorite decade of music?

10. If you could invite one artist to your wedding, who would it be?
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11. Is there a fictional character you’d want to be more like?
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12. Would you rather have someone act hostile to your face or pretend that they like you?

13. How does a rainy day make you feel?
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14. What’s your favorite type of exercise?
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15. Who is your favorite athlete?

16. Which college did you go to?
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17. What were your majors in school?
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18. Did you ever cheat on an exam?

19. What career path are you pursuing?
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20. Were you excited to start working when you were finishing school?
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21. Have you ever suffered for being different?

22. Would you consider dumpster diving?
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23. Would you say you’re closer to your parents or grandparents?
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24. What is your favorite local restaurant/cafe?

25. Do you try to support local businesses over large corporations if you have a choice?
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26. What really pumps you up and gets you going?
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27. What’s one thing you do regularly and would never skip?

28. What are your thoughts on thrifting?
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29. What’s one tourist attraction you’d love to visit the most?
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30. Do you prefer simple food, or would you rather go for interesting combinations of flavors?

31. How do you feel about getting pranked?
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32. Do you often get embarrassed for other people?
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33. Do you prefer games in which you cooperate or play against one another?

34. What was your first car?

Personal questions to ask a guy you like

These questions will allow you to get to know a guy you like at a personal level. Personal questions are also good to keep a conversation going with a guy. The best time to ask these questions is when you are comfortable starting to open up a little with each other.

1. When is your birthday?
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2. How many siblings do you have?
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3. Who is your favorite sibling?

4. Would you like to get married?
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5. Would you like to have kids? If so, how many?
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6. What is your greatest fear?

7. Where do you see yourself in five years?
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8. How do you measure or define success?
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9. Are you religious?

10. Is it easy for you to make friends?
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11. What is the most unhealthy habit you have?
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12. Have you ever experienced some sort of abuse?

13. What is one thing you can never compromise on when it comes to relationships?
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14. What is your greatest personal value?
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15. Have you ever written a published piece of work?

16. Do you think tertiary education is necessary?
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17. What is your favorite music genre?
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18. Would you consider gambling?

19. Have you ever thought of starting a new life somewhere?
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20. Do you ever feel like an outcast?
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21. Has anyone in your family been directly affected by war?

22. How would you describe the relationship you have with your parents?
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23. Have you ever had a sequence of things going wrong for you?
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24. Have you ever participated in a ritual or a ceremony of any kind?

25. Do you think any job/profession is beneath you? If so, what is it?
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26. Have you ever bullied someone?
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27. Are you proud of your family?

28. Do you ever feel like your family is trying to pull you down?
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29. Have you ever argued with your significant other in public?
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30. Have you ever physically hurt anyone?

31. Is it important to you that people remember your birthday?
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32. Do you ever feel like there’s nothing left to do in life?
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33. Would you say you’re good at managing money?

34. Have you ever doubted your own sanity?
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35. Did you ever talk back to your parents when you were a kid?
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36. Have you ever been emotionally affected by a band splitting up?

37. Is there an area of life in which you’re jaded?
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38. Have you ever wanted to be a vigilante?
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39. Have you ever successfully gotten over an addiction?

40. Would you say public opinion influences yours a lot?
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41. How do you keep up your motivation when things get tough?
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42. Do you have any exciting childhood memories?

43. Is it easy for you to express your emotions?
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44. What is on your bucket list?
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45. Would you move to a different part of the world and be away from your family?

46. What is your sexuality?
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47. Have you ever questioned your sexuality?
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48. Have you ever cheated on your partner?

Deep questions to ask a guy you like

These questions will allow you to get to know him at a deeper level and engage in deeper conversation. Once you know the basics about him, you can go ahead and ask any of these profound and meaningful questions.

1. Would you rather have an IQ below average and be happy or have a very high IQ and be miserable?
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2. If you could change one thing about yourself, what would it be?
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3. Is it wrong to steal from a thief?

4. How tempted do you think you would be by bribes if you were in a position of power?
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5. How do you decide on what’s important in life?
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6. What do you think is the best way to get to know someone?

7. What do you think happens after we die?
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8. Do you think society is moving in the right direction?
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9. What do you think about humans moving to other planets?

10. How do you define death?
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11. Would it be all bad if we went back to the Stone Age, technology-wise?
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12. Would you rather be super rich or super bright?

13. Do you think the internet has more positives or negatives?
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14. What do you think about universal basic income?
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15. What does it mean to “sell one’s soul”?

16. Which historical fact fascinates you the most?
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17. What’s scarier than death?
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18. In which situations is “fake it till you make it” a good plan?

19. Do you think our destiny is predefined by fate?
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20. What are your thoughts on religion? Do you think it has brought more good or evil?
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21. What are your thoughts on open marriages/relationships?

22. Would you consider being married for convenience?

Flirty questions to ask a guy you like

Well done on accepting that you have a new crush! Now what?

Sometimes when we realize that we like someone, we lose our ability to communicate. We have no idea what to say to them, and we are scared we might say the wrong things. This list will redeem you from that misery. The best time to ask these questions is after you have established a friendship with a guy.

1. Are you in a relationship?
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2. How’s a guy like you still single?
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3. How did your previous relationship end?

4. Which one of your body parts most needs a massage?
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5. Appearance-wise, what’s my best feature?
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6. What’s the most fun location for a date?

7. What clothes make me look the best?
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8. Have you missed me?
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9. Do you have any hidden talents?

10. We’d have beautiful kids together, you know?
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11. What kind of kissing do you prefer?
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12. What is your biggest turn-on?

13. Wouldn’t it be romantic to get stuck on top of a Ferris wheel?
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14. Do you mind being my plus one at an event?
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15. What’s your biggest fantasy?

16. What kind of nickname can you imagine giving me if we were married and living together?
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17. Do you like girls like me?
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18. What’s your sexiest body part?

19. Are you a romantic?
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20. What are the qualities you look for when deciding to date someone?
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21. How would you describe your ideal first date?

22. Do you believe in soul mates?
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23. Do you think I am your “type”?
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24. What is the most romantic gesture you have ever done for someone?

25. What is the most romantic gesture someone has ever done for you?
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26. Would you ever date someone older than you?
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27. How long was the longest relationship you have ever been in?

28. Would you consider being in a long-distance relationship?
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29. If I were to invite you over for a movie, would you come over?
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30. When you see or plan your future, do you see me there?

31. What is your best quality as a boyfriend?
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32. Do you believe in love at first sight?

Fun questions to ask a guy you like

Ask any of these questions to create or maintain a lighthearted and fun environment. When you see that the guy you like is starting to get uncomfortable, these questions can rescue the situation and make it fun and relaxed.

1. Would you turn into a vampire to gain eternal life if you had to prey on other people to survive? No animal or donor blood is allowed!
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2. What are the two words that shouldn’t go together?
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3. What’s the most random fact about you?

4. What would your version of hell look like?
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5. What are the worst two diseases to have at the same time?
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6. What’s the most embarrassing event you’ve participated in?

7. Which language would you like to learn and why?
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8. Have you ever gotten a pedicure?
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9. Can you do any celebrity impressions?

10. What’s the worst case of Catch-22 you’ve ever experienced?
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11. If you could resurrect one person as a zombie, who would it be?
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12. If you time-traveled to the time before you were born, what would you say to your parents?

13. If you’ve invented a dance, what would you call it?
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14. How do you picture yourself as a grandparent?
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15. What’s the best thing that originated from your home country?

16. Do you ever make faces at yourself in the mirror?
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17. What is your favorite flavor?
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18. Would you agree to give up internet access for a million dollars?

19. Would you rather go out or stay in?
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20. What is the fashion trend you would never follow?
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21. Which movie cliché do you hate the most?

22. Which artist would you bring back to life?
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23. What is the longest you have ever gone without a phone?
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24. What is your all-time favorite cartoon or animation?

25. Which Disney princess would you marry?
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26. The last time you dressed up for Halloween, who/what did you dress up as?

Questions to ask a guy you like over text

In this digital age where many conversations happen over text, you might find yourself unsure of how to keep the conversation going. This list has questions you can ask over text to keep the conversation flowing.

1. Would you want to know more about your parents’ past lives than what they’ve told you?
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2. Which one of your family members has the best sense of humor?
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3. What’s the strangest dish you ever came up with on your own?

4. Do you save memes?
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5. What is your opinion on news outlets that push a certain agenda?
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6. What’s one thing you’re really good at?

7. What’s the scariest book you’ve ever read?
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8. What would your parents say or do if they found you smoking weed as a teenager?
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9. What would it take for you to go vegan?

10. Have you ever been in a car crash?
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11. How often do you work out at the gym?
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12. Do you have a tattoo?

13. Would you consider having a tattoo of your partner or girlfriend?
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14. Which historical figure would you like to meet?
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15. Would you say you are or ever were a part of any subculture?

16. How do you feel about “renting” digital media?
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17. If you could shapeshift into an animal, which one would it be?
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18. Have you ever donated blood?

19. If you won a huge lottery prize, would you rather get it all at once or split it into monthly payments for the rest of your life?
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20. Would you rather get 5 million dollars or go back to being ten years old with the same amount of knowledge you have now?
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21. What is one superstition you have never believed?

You might be interested in our guide on how to text a guy you like.

Random questions to ask a guy you like

What better way to have fun with the guy you like than by asking some random questions? These questions will put him in a position where he has to think about some things he likely would have never thought about.

1. Splitting chores, would you rather clean the toilet or take out the trash?
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2. What’s your favorite sound?
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3. What’s the most significant sum of money you’ve ever found lying on the street?

4. Do you consider coffee a drug?
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5. What is the one sport you never understood?
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6. Do you have a favorite planet, other than Earth?

7. What was your first phone?
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8. How often do you trim your nails?
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9. What do you consider to be the best brand of potato chips?

10. If you could create a new flavor, how would you describe it?
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11. Coffee or tea?
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12. Would you consider having a personal chef?

13. Have you ever experienced sleepwalking?
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14. If you had all the money and all the time in the world, what would you do?
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15. What is the most extreme thing you have ever done to keep a girl?

16. Do you believe in the afterlife?
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17. What is the most expensive thing you have ever bought yourself?
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18. What is your take on luxurious brands?

19. Who is your celebrity crush?
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20. Have you ever ghosted someone?
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21. What is the longest you have ever gone without seeing your family?

22. Who is your favorite superhero?
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23. If you could give up one sense which one would it be?
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24. Big or small wedding?

Weird questions to ask a guy you like

These are interesting and engaging questions that will likely make him laugh or wonder how your brain works. Ask any of these questions, and you might be surprised with where the conversation ends up going!

1. How would you describe the difference between the taste of instant and ground coffee?
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2. If you could be a mage proficient in elemental magic, which of the four elements would you study?
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3. If you were an infamous thief, would you want people to know who you are for the bragging rights?

4. Would you plan your funeral?
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5. Would you rather go completely bald or have hair that grows way too fast so that you have to trim it twice per day?
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6. Would you date the female version of yourself?

7. Do you ever stare and appreciate your own reflection?
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8. Do you ever treat computer files as people that have personalities? For example, by arranging them into their folders so that they’d live together in their little folder apartments?
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9. Which celebrity has a personality that is the most similar to yours?

10. Do you ever feel guilty about eating a really beautifully plated meal because it feels like you’re destroying a work of art?
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11. How is bubblegum a flavor when bubblegum comes in different flavors?
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12. When you have a stack of money or organizing cash inside your wallet, do you prefer to have higher or lower value banknotes to be more visible?

13. Do you prefer thinner or thicker slices for your sandwiches?
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14. Do you prefer the beginning of a year or the end of a year?
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15. If you were a food, which one would you be?

16. What’s more satisfying to write with: a pen, a pencil, or a marker?
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17. Have you ever considered having an OnlyFans account?
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18. Have you ever been attracted to your teacher?

19. Would you consider being in a relationship with a married woman if she is interested?
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20. If you were stranded and all the people you were with died, would you eat them so that you survive?

Awkward questions to ask a guy you like

These questions will likely create an awkward environment if asked too soon. Ask these when you are both comfortable being around each other. Keep an eye on his body language as he responds to these questions.

1. Have you ever mistreated a waiter?
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2. Have you ever seen a relative naked?
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3. How do you feel about your most recent ex?

4. How much do you think I weigh?
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5. Do you catch yourself treating people unfairly?
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6. Have you ever stolen from a hotel?

7. How old do you think I am?
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8. Have you ever enjoyed lying?
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9. Do you ever google new acquaintances?

10. What was the most embarrassing moment in school for you?
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11. Do you ever cry at movies?
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12. How would you rate your own intelligence?

13. Do you ever struggle with being honest or genuine?
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14. Have you ever hallucinated?
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15. What happened the last time you lost your temper?

16. When is it totally appropriate for a guy to cry?
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17. What’s the most disgusting thing you’ve seen on the internet?
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18. Which body part would you get plastic surgery on if it was free and a positive result was 100% guaranteed?

19. Are you embarrassed by any of your close relatives’ beliefs?
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20. What is your body count?
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21. What fetish do you find the weirdest?

22. What is the longest you have gone celibate?
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23. Do you watch pornographic material?
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24. How do you handle a situation where a girl hits on you?

25. Have you ever found a guy attractive?

Viktor is a Counselor specialized in interpersonal communication and relationships. He manages SocialSelf’s scientific review board. Follow on Twitter or read more.


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