Top 20 Best Ice Breaking Conversation Starters

photo_21523_20120317Kevin, is brand new at the dating game was clueless when it came to “chatting.”

He was a superb interviewer and adroit cross-examiner, and eloquent closing argument kind of a guy…He was too nervous for small talk on a first, (or second, date.)

He asked me for 10 – 20 Opening Lines/Ice Breakers when talking to ‘Someone of the Opposite Sex.’   Voila!

 The Top 20 Questions to Break the Ice


1. Tell me about your best friend.

2. Tell me about your very worst job.

  1. What was your very first car?
  2. What was your very best job?

5. Tell me about your family and where you grew up.

6. Tell me about your very favorite relative.

7. Tell me the Top Five places you’ve worked

8. Who is your all-time favorite female movie star?

  1. What passions / hobbies do you spend money on?
  2. What’s you very favorite song?
  3. Tell me one really life-changing moment?
  4. When did you meet your very first girlfriend/boyfriend?
  5. Where and when was your first kiss and with whom?
  6. What is the silliest thing you have ever done?
  7. What is the worst prank you’ve pulled?
  8. Tell me the most romantic date you’ve ever planned.
  9. They say, “Women shop and men buy.” What is one store you wouldn’t be caught dead in?
  10. Alaska or Hawaii – what is your choice?
  11. Tell me what your perfect day-off looks like?

20. If someone gave you two free tickets to anywhere in the world – where would you go?

photo_8735_20081228 Note To  Beginner Dater: Refrain from asking all these questions – at once- to the same person.

Your goals to create a conversation – not conduct a job interview.

Have fun out there!

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This entry was posted in Dating at 50, Page Larkin Marin, Relationship, single in Marin, Uncategorized and tagged , , , , . Bookmark the permalink.

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