I was invited to Valve's Game Developers Conference after party. I met Felicia Day and swing danced with her. She's super fucking cool. During that same GDC, I started interviewing at Riot Games and ended up getting hired by them.
There's other fun stuff I've proactively done, but I think that's the big one that happened to me
I answered a ringing payphone in an otherwise empty train station. Life goal achieved!
I also spent a week surviving in the wilderness a couple times, slept out for multiple days in below-zero temperatures, built and slept in a snow-dome shelter, and so on, but that's just life in the Scouts.
And I judged the world's largest annual scavenger hunt for years.
Thank you! I was really tempted to try to put moves on her, but I was in a relationship at the time. When I got home and told the story, my girlfriend at the time said she totally would have given me a pass. I have regrets. Of course, I probably would have failed anyway, but it's fun to think about.