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40+ Questions To Ask A Guy You Like (Or To Any Guy In General)

No more awkward silences!

Running out of things to talk about with your crush/boyfriend? Want to get him talking but don’t know where to start? It’s time to start asking questions. Most guys love it when you show a concerted interest in their lives, and you’ll also have the chance to get to know him better!

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If you don’t know what to ask, we have you covered! Read on for 30+ great questions to ask a guy.

RELATED: Rapid Fire Questions with Tim Franklin

21 Questions To Ask Your Crush

Looking for funny or flirty questions to ask on a first date? These should do the trick, but prepare your own answer to them in case he turns it around! Some of these could also work for friendly interactions… if you’re just testing the waters for now.

  1. What’s your favourite book?
  2. What’s the best sign that you have chemistry with someone?
  3. What do you like doing in your spare time?
  4. Who was/is your favourite teacher in school?
  5. Do you like small talk?
  6. On weekend nights do you like going out or staying in?
  7. What’s the most embarrassing thing that has ever happened to you?
  8. What’s the best compliment you’ve ever received?
  9. What are your thoughts about splitting the bill on a first date?
  10. What’s something that’s considered manly that you can’t actually do?
  11. Would you say that you’re in touch with your feminine side?
  12. Have you ever cried in public?
  13. What’s the best way to unwind after a long day?
  14. What is something people do that annoys you?
  15. Can you describe the strangest situation you’ve ever found yourself in?
  16. What’s a movie that you can never get sick of rewatching?
  17. Do you like dancing?
  18. What’s your favourite item of clothing?
  19. How would you feel if your date was taller than you are?
  20. What’s your favourite food?
  21. What’s the most fun you’ve ever had?
A couple on a date in a cafe
(Credit: Getty)
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20 Questions To Ask Your Boyfriend

Don’t think you know your partner too well? Here are some zingers you can throw at him on a chilly evening. Be warned: some of these can get pretty deep and dirty.

  1. What’s something that I do that annoys you, but you put up with anyway?
  2. Would you consider getting a pet?
  3. Do I know all of your secrets?
  4. What’s something that I do that turns you on?
  5. What’s the weirdest thing you’ve ever had to do for a partner?
  6. When did you think you “officially” became an adult?
  7. How did your first kiss go?
  8. Who’s your celebrity crush?
  9. Would you love me if I had no limbs?
  10. What’s your favourite quote?
  11. Is there something that you’ve ever had to give up for love?
  12. What’s your opinion on public displays of affection?
  13. What’s a naughty secret about me that only you would know?
  14. Was there ever a time that I didn’t pick up on what you wanted?
  15. Who’s your best friend? Any why?
  16. What’s your favourite childhood memory?
  17. Do you pick your nose?
  18. What’s the sexiest thing about me?
  19. Was it easy asking me out?
  20. At what point did you think I was girlfriend material?
A girl and a guy looking at each other while sitting on a couch
(Credit: Getty)

10 Other Questions To Just Ask Guys

Whether they’re friends, co-workers, or just random people you met at a party, here are some questions that you can ask any guy. From the weird to the profound, these should make for some interesting conversation.

  1. Do you prefer peeing sitting down?
  2. What kind of person do you try to avoid associating with?
  3. Who are you most jealous of?
  4. Would you like to swap bodies with a girl for a day?
  5. Have you ever been in a fight?
  6. What’s your most useless talent?
  7. What is your greatest fear?
  8. What is the worst job you’ve ever had?
  9. What’s your favourite song of all time?
  10. What’s your favourite video game?

RELATED: Questions to ask on a first date

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