The biggest chuckle I got from a stranger pirate was one time I was standing on the dock just checking out my weapons. Now keep in mind that Disney gave me options and I just chose one. I'm also probably one of the older players in the game.
A female pirate, covered head to toe (must be hot in all that stuff on the islands) came up to me. Said "Put some clothes on"! and TP'd away.
Personally I found that quite amusing and it made me wonder what this person was like in RL.
But ummm yeah....don't take my flag ship please?