Wow, Ruby, what a great topic! I love the idea. Since my Dad is getting older, he's been telling me stories he's never told before -- what it was like in Pearl Harbor, stuff he just didn't want to talk about when he was young. And I love these stories!
"something that happened that was sad but turned out good"
-- or "the first person you fell in love with, and why did or didn't it turn out"
-- or, "the first pet you ever had" (in my family, it would be chickens and goats)
-- or how about "the first time you knew you were good at something"
-- "the best Christmas gift you ever gave or received"
-- "the worst thing that ever embarrassed you"
-- "the best book you ever read, and why it caught your imagination"
-- "what was the meanest thing ever done to you (or the meanest thing you'vbe ever done)"
-- "what was the nicest outfit you ever wore, and why did you love it so much?" (I expect this will work for women best)
Thank you so much for starting this topic, Ruby! You have my imagination going.....
Oh, and maybe one for myself -- "when was the last time you left your bra in a limo, and why?"