Have you ever had that awkward dead space when you start speaking on the phone with a new potential date, and you wonder if you are coming across as an uneducated idiot? Well, I can’t help you if you’re on a date. It would look a little odd to pull out your notebook and start firing questions in his direction, but if you are having a phone call prior to meeting him use some of my suggestions below to have an ease of conversation, and wow him with your thought-provoking leading questions.

  1. Tell me one thing that’s on your bucket list. 
  2. What kind of childhood did you have
  3. Are your parents still living? Do you have siblings?
  4. Where did you grow up?
  5. What do you find attractive in a woman?
  6. If you could describe yourself in one word what would it be?
  7. What’s your favorite/least favorite food?
  8. How is someone like you single?
  9. What’s your biggest turn on?
  10. What’s your idea of a perfect date?
  11. What’s your favorite place you’ve traveled to?
  12. What do you do for fun?
  13. If you could give a TED talk tomorrow, what would it be about?
  14. What long shot have you taken that has really paid off?
  15. What’s one question you can ask someone to find out the most about them?
  16. What’s your secret fetish? You must have one…come on.
  17. What are you so incredibly terrible at that you’ve given up ever attempting again?
  18. What’s the worst and best thing about being a man?
  19. What’s the number one thing people would never know about you just by looking at you?
  20. What’s one thing you still want to do that you haven’t?
  21. If you had to choose one cause to dedicate your life too what would it be?
  22. What was your closest call?
  23. How does your definition of a real man differ from the mainstream stereotype of a man?
  24. What are you determined to do?
  25. What do you wish you knew more about?
  26. What gets you fired up?
  27. What’s the best single day in the calendar?
  28. What’s worth spending a bit more on to get the best?
  29. How do you \relax after a long day’s work?
  30. What are you looking forward to in the next few months?
  31. What was the most memorable gift you ever received?
  32. What’s the most annoying habit other people have?
  33. When people come to you for help, what do they usually want help with?
  34. What is something you think everyone should do at least once in their lives?
  35. What’s your favorite possession and why?

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