I like meeting all the characters and I like meeting them each time I go to Walt Disney World. When we went in 1998, I let the kids focus on them. When I went back in 2017, I wanted in on all the fun.
I don't remember much "special" about this interaction. I mean, Cinderella was pleasant, of course! I just don't remember delving into any of Kenny the Pirate's hints to make this more interesting.
I plan to do better next trip! Maybe ask her for some cleaning tips or helpful advice on mouse problems?
You meet Cinderella on a non-COVID 19 regular type basis at Fairytale Hall behind Cinderella's Castle. She can also be found during breakfast, lunch, and dinner at Cinderella's Royal Table table service restaurant in the castle. During normal operations, Fastpass+ is available for this meet and greet.