Whenever you have a crush on a guy—whether it’s a coworker, a classmate, a peer, or someone you met on the street, you are going to want to learn more about them. To help you out with a starting point, the following are typical questions to ask a man.

Top 25 Questions to Ask a Guy You Have a Crush On

When you have a crush, you are more enamored with their looks than their personality. However, for a future relationship to function appropriately, you need to learn more about this guy and his personality by using these questions.

1. Would you prefer to be smart or happy, and why?

2. If you could choose one superpower, what would it be and why?

3. What is your biggest regret in life so far?

4. If you could marry a fictional character, who would it be and why?

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

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

7. What television show do you plan your day around in order to see it live?

8. What extracurricular activities or sports did you participate in when you were in high school?

9. Of all your pet-peeves, which is the strangest?

10. Is it better to beg forgiveness or ask permission?

11. If you inherited or won a million dollars, what would you do with it?

12. What is the most embarrassing thing that has happened to you?

13. Which fictional character do you believe is the most like yourself?

14. Are you superstitious? If so, what are you most superstitious about?

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

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

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

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

19. What are you three weaknesses?

20. How would you describe yourself in three words?

21. Which is more logical to follow—your heart or your head?

22. Are you spiritual or religious in any way? If so, how?

23. If you could have any career possible, what would it be?

24. Have you ever been arrested or contracted any diseases?

25. Which is better—a novel or a movie?

Top 25 Funny Questions to Ask a Guy

Yes, it’s important that the questions you ask are genuine and reasonable, but what’s the harm with having a little fun on a first date as well. When you need a break from serious questions, try some of the more hilarity-inducing options, such as these:

1. If your life was a movie, which actor would play you?

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

3. How do you handle people you don’t like?

4. Is it possible for us to have met previously, in another life?

5. Where would you prefer to live: beach, city or country?

6. If you had met me before, how would you describe me?

7. Do you think of yourself as being naughty or nice?

8. Who is or was your celebrity crush?

9. With whom did you have your first kiss?

10. What is your favorite type of food?

11. What is your favorite genre of music?

12. What is your all-time favorite movie?

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

14. What is the funniest thing you have ever done or said?

15. Have you ever been caught naked by someone?

16. What is your funniest childhood memory?

17. Are you more of a night owl or a morning person? This is one of the questions to ask a guy that will lead to more questions and make the conversation flow smoothly.

18. What is your greatest fear?

19. What do you believe I am thinking right now?

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

21. Which famous celebrity would you like to date, and why?

22. While in school, did you ever cheat on a test?

23. If you could read minds, whose would you want to read?

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

25. Which animal do you consider to be the sexiest?

Tips
  • These are meant as a starting point, not a set-in-stone list of questions. Use this list as a guideline to either pick and choose from, or inspire questions you realize you really want to ask.
  • If you are having a good conversation with the guy you like, do not interrupt to ask him some of these questions. Instead, go with the flow of the conversation and learn about him that way—it’ll probably be more authentic.
  • Whenever there is an awkward gap or silence in the conversation, these are great questions to ask a guy.
  • Remember to use questions which will create story-like answers rather than simple yes or no answer. For example, “Where were you born?” will be only answered boringly compared to, “What was your childhood like?”
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