Max, there are two instances in the past couple of years I could kick myself over. One was when I was leaving Aspen two summers ago. I flew in privately and out commercially. I really don't like leaving Aspen and would move there in a heartbeat if I could. I was sitting in the small terminal and there happened to be a cute young woman my age on the row of seats on the otherside of the row of seats. She was on crutches! Perfect ice breaker - I'm not great at opening my mouth in the beginning either. Weather was bad and the incoming flight was delayed, so wee had a chance to chat for a bit - this scenario would have completed your challenge
. Flight is eventually cancelled and I call dad to get me from the airport and I tell him that we will be giving her a ride back to her friends condo.
I can't say I was totally attracted to her, but in the course of chatting, I thought, "hey, if we can meet up again and go ouht for coffee, drinks, whatever, that'd be cool and what ever happens, happens. I did all the appropriate things, carried her luggage and mine, opened the car door for her, insisted that she sit in the front pax seat....
End of the story is that I only got her first name and she mentioned finding me on Facebook. She caught an earlier flight the next day and I never saw her again. When my dad and I left that condo complex, I mentioned that I was an idiot for not exchanging numbers. He agreed.
I missed the chance to really get to know someone. Maybe it would have gone somewhere, maybe not. I'll never know, because I screwed up.