50 questions to ask a man you like


Breaking the ice with a man you like can be a real challenge sometimes. It can also be difficult to cross the barrier between being two friends and being two lovers.

If there is one thing that I dread when I meet a man that I like but that I don’t really know, it’s the long silences. Often I feel so uncomfortable with these long silences that I break the ice by saying the first thing that comes to my mind, even if it’s stupid …

So to avoid this kind of mishap, I keep a list of questions to ask a man I like. This list is perfect to use when you’re afraid of long silences and looking for conversation topics.


At the beginning of my relationship with my man, we could spend several hours face to face asking questions. It’s a great thing to do to learn more about a man, his personality, and his character.

One very important thing about questions and conversations, in general, is that they are useful in getting to know you. Not for impression that man you like. Far too many people forget this advice and just try to talk about how interesting their life is. Even if this is not true.

Remember the most important thing when asking these questions of a man you like: Don’t be too serious when asking the questions and try to take pleasure in discovering this man’s personality. It may be your future husband!

All of the questions below are selected because I find them to be questions for getting to know someone even if you’ve never seen each other before.


  • 1. What’s the best way to end a successful day?
  • 2. If you inherited 10 million euros, what would you do with your life?
  • 3. If you could marry a movie character, who would it be?
  • 4. What is your favorite quote?
  • 5. How would you describe yourself in 3 words?
  • 6. What would you do differently if you knew that no one could judge you?
  • 7. Something you’ve never been good at?
  • 8. What moment in your childhood is your favorite?
  • 9. If you had to lose one of your 5 senses, which would it be?
  • 10. If you could make a wish what would it be?
  • 11. What was the most difficult time in your life?
  • 12. What kills love can make the most beautiful of women the ugliest?
  • 13. Finish the sentence: The world would be a better place if ________
  • 14. Do you believe in love at first sight?
  • 15. What is the best compliment you have received?
  • 16. What always puts you in a good mood?
  • 17. What is it that always makes you angry?
  • 18. What mistake will you never make again?
  • 19. What are you doing as much as you can to feel good?
  • 20. If you could change one thing in your life, what would it be?
  • 21. One thing you will never let someone do to you?
  • 22. When was the last time you cried?
  • 23. Do you believe in love?
  • 24. Something you can never forgive?
  • 25. What’s the biggest lie you told?
  • 26. What do you like the most about yourself?
  • 27. What do you like the most about me?
  • 28. What will your life be like in 1 year?
  • 29. What stresses you out every time you do this?
  • 30. What was your favorite game when you were a kid?
  • 31. What is your biggest dream?
  • 32. What is the greatest quality in a woman?
  • 33. What do you like about a woman?
  • 34. What is the thing you own that is most valuable to you?
  • 35. Something you never get tired of?
  • 36. Do you think social media is a good thing or not?
  • 37. If you could give $ 1 million to charity, which one would it be?
  • 38. If you were to die in 1 month, what would be the 5 things you would do?
  • 39. What is the best part of the day?
  • 40. Do you believe in spirits?
  • 41. What is the worst flaw a person can have?
  • 42. Do you believe in reincarnation?
  • 43. What is your favorite song?
  • 44. What always makes you in a good mood?
  • 45. If you could relive a year of your life, which year would it be?
  • 46. ​​If you could be a woman for a day, what would you do?
  • 47. Your house is on fire, what are the three unusual things you take?
  • 48. Would you like to be famous?
  • 49. Who is the person you admire the most?
  • 50. Do you want to go out with me?

Here is my list of questions to ask a man you like. I hope that with this list you will be able to find plenty of subject of conversation to avoid the blanks and especially get to know this man who is the center of your thoughts.

Try to tell him to answer these questions in full detail. Certainly we can answer it with yes or no, but it is much more interesting if you give details and explanations on the answers.