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 guy.

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 to ask a guy 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 to ask a guy, 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?

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?

  • These are meant as a starting point, not a set-in-stone list of questions to ask a guy. 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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  • maryamSep.25 15:08
    There's this this guy I really like, we don't talk that much. I already told my mom about him, but not my dad, my dad still thinks I'm his "little girl". We're in different classes and if I ask him out he might say no 'cause we're only ten.
  • MaysaSep.2 00:03
    Hi my name is Maysa I like a guy and he is lebense but in a couples day he left her and now I'm liking but he is moving a away from me
  • JenniferJul.14 05:09
    Some Guys are shy or afraid of to ask me questions and I don't know why they think it's cute if girls blush lol or laugh they think it's attractive, which is cute lol...
  • GameboyJul.14 01:16
    The funniest questions to ask a guy: a) If you say you are a muscular man, could you lift up your own heart to let me see? b) If you say you are a handsome man, could you see yourselves to be handsome especially your face without the use of any mirror or materials that could reflect your physical body or even photos?
  • GameboyJul.14 01:09
    The funniest questions to ask: a) Hey! Guy! If you say you are stronger than other guys, could you lift up your own weight? b) Hey! Guy! If you say you are rich, can you buy your heart? c) Hey! Guy! If you say you are a good cook, can you cook pig's brain with bean curds?
  • AlsJul.5 19:43
    These questions did work to help keep the conversation going. ????
  • boluwatifeJun.7 23:47
    asking questions makes you smart
  • Yer MawMay.24 12:46
    I hate this website it manipulates cats and stops Bradley from talking thanks a bunch you fails.
  • Netta May.18 18:00
    There is this guy- friend of mine who has trust issues but for some reason he confides in me with all his problems/emotions. He believes I understand him but that is about it. I don't know what to make of him
  • JazzyMay.5 05:22
    I know this one guy and he likes me and I like him but he's a year younger than I, and my family is really close to his family. His family knows that he likes me but mine only has an idea I haven't confirmed anything yet and I don't know if I should go out with him or not. He's really sweat, kind and he's greattach with his family. I just don't know if I should go out with him or not. What shall I do?
  • MaryamSep.25 14:33
    @ : @Jazzy, if you like the boy and he likes you back, just ask him out. Age doesn't matter.
  • MaryamSep.25 14:42
    @ : I suggest to tell your family how you feel first.
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