I have never met Paul but twice (2010 and 2014), my wife and I waited outside a venue in Salt Lake City for his arrival in a car. Both times, he rolled the window down and said hello to all us fans lined up. The first time in 2010 it was scorching hot outside and my wife was not thrilled with me making us wait a couple of hours for his arrival. But when he arrived and we saw him up close in a car and he said hello it was absolutely thrilling. Thus, in 2014, she was glad to stand in line and once again thrilled to see him so close. Those two fleeting moments were among the favorite of my life to be honest. I did talk to his security guy Scottie both times, nice chap.
Then in 2005 in Portland, my wife, mother, and I had tickets on the side of the stage in a small section (maybe 150 people in the section). When the concert ended, the crowd cleared out. We waited and Paul had gone down to the side of the stage with his guitar guy/roadie (John Hammel). Paul looked up to our section and waved, the three of us waved back. I looked behind me and our entire section was gone except for us so Paul waved to us. We all realized that Paul had waved directly to us and that was a funny feeling. That was a quite a moment and it still gives me goosebumps to describe it.
I often think about meeting him and what I would say. I imagine seeing him in Yellowstone or the Idaho wilderness where my expertise in that area could lead me to have a discussion with him. Perhaps, I could take him on a hike? (ha). I will likely never meet him but the three moments that I just described were pretty darn cool.