I have a few pro stories, none that weird though.
One time I rocked up at my local in Sydney Australia, this shithole skatepark I'd skated at for years, and Grant Taylor, Greyson Fletcher, and a few other Nike dudes were there. Grant was blasting enormous frontside airs on the quarter pipe, and Greyson ended up giving me and my friend a set up and a used deck he had been skating. Legend.
On another occasion, I was at Manly beach one time looking for this hot pro surfer girl Alana Blanchard (there was a surf comp on at the time.)
While walking to the beach, I look into an Oakley store and I see Eric Koston inside randomly. As a sheer reflex, I shout "Koston!" and he looks at me and walks out of the store (where he had been doing a signing), and begins to talk to me for about five minutes. I got a photo with him, and proceeded to continue looking for the hot surfer girl.
As I continue my walk down the beach, I see Austyn Gillette walking toward me. Again, I reflexively say "Austyn!" and he comes over and chats to my friend and I. Austyn was much quieter than Koston and after about a minute he informs us that he was actually on his way to go piss, and he shook our hands and continued walking.
Then, we saw that there was a Nike booth being set up on the beachfront, so we sat on a little ledge waiting to see what pros would be signing autographs. As we're sitting there, Lance Mountain begins to walk in our direction. I waved at him and he came over and shook my hand, and I said I was a big fan. (I wasn't really, I knew who he was but had not really seen much footage of him prior to this encounter.)
We continue sitting on this ledge, and GT and basically the entire Anti-Hero team rock up, and sit right next to us. I then see Dylan Rieder smoking a cigarette in front of me. I was a big fan of Dylan at the time, and really wanted to get a picture with him, but he had lines of girls coming up to him asking for photos, and there was the entire Antihero team right next to me so I felt like I'd look like too much of a fanboy.
I was even wearing Gravis at the time, and Dylan eventually sat down pretty close to me and I kept noticing he would look over, probably knowing I was a fan (Gravis had already died at this point, so I was wearing relics of his old company) but I proceeded to pussy out and not speak to him.
Finally, the Nike signing gets set up and I got autographs from a few dudes, Shane O'Neill being one of them.
I don't know if any of this is interesting or it's just me rehashing a star-studded day, but it was certainly a memorable experience. I've not really had any bad experiences with pros.
LASTLY, I went to the city one time and I saw the DC team, Mike Mo, Mikey Taylor, Chris Cole and some others skating at Martin Place. We sat down to watch, and Mike Mo was rifling off tricks down the three 3 stairs. Mikey turned around and said to us "god damn he's so good" and we just smiled and nodded and continued watching in awe.
All of these chance encounters are pretty absurd given how isolated Australia is. It's like seeing a legendary pokemon in the wild.