Yes, conversations with strangers are much easier at WDW. Maybe it is just the atmosphere, or other peoples fun attitudes make you want to speak to them. Now, mind you, there are always the party poopers in every park, the ones obviously having a lousy time, or are concentrating so hard on doing as much as possible that they miss the whole point. It is not easy to speak with these types, or even want to.
One thing I like to do is if I see a family taking a group picture, and one of them is not going to get to be in the shot, I'll ask them if I can take the picture for them so everyone can be in the picture. Another is a couple who are taking pictures of each other. They usually really appreciate having some together pictures. Since I have quit carrying around all my camera stuff, I don't take many pictures for us so I usually don't spend a lot of time taking pictures for others, but it is fun to offer occasionally.
Oh, Jennifer I thought that same thing about never seeing these people again. Last year we were at the GF, looking at the big gingerbread house and I nearly ran all over this woman. I just was not paying enough attention to my surroundings. We had a good laugh about it and spoke briefly about how beautiful the decorations were. About 3 months later, in a mall in Atlanta this woman came up to me and jokingly said "OK, pay attention to where you are going". It was her. Turns out she lives in North Georgia too. She and my wife spoke about shopping and we had another good laugh and went on our way.
Ricky