Flirting? Never done it, but I probably should. I'm not getting younger and the few opportunities have slipped away far too easily. I was always the awkward/shy/this-space-for-rent person who decided to be friends first and then ask. A strategy that appears very poor as that number dwindles.
True story: I was late for work and this nice-looking/not-particularly-hot/advertise-your-brand-here young lady was sitting to my right across the aisle on the train. This was the South Shore Line from Chicago to Hegewisch and Points East. I was in a funk because I was late, my car was in the shop, and whatever else was wrong with the world, but it didn't escape me that she had been looking over at me. I'll admit it: I take a perverted pleasure in the turmoil in people at moments like this. I don't have to do anything and she'll just get more and more agitated. But I also knew that I would/could never be on the train this late on this day of the week - so I was unlikely to ever see her again. Finally, as we were getting close to her stop:
She: "Excuse me, what time is it?"
Me: "Um.. about 10:30?" It just slipped out, and it was completely wrong. I don't even know why I said that. It would be 10:30 if I wasn't 2 hours late getting to work. Her earnest expression switched to shock.
She (blurting out): "You're crazy!"
I really did intend to follow up with witty banter, when she finally spoke. Yet when she said that, all I could do was remark to myself how perceptive she was to say that. And then she got up and left. And I missed out on another one. Pity. Oh, she probably was not Happiness wrapped up in a bow, but its my loss for not finding out for sure.