When I went to WDW way back in 7th grade, we ran into someone else from our school there (from North Dakota). This also happened to me in 10th grade. My family went to Hawaii and a fellow classmate ended going AND being in the very same hotel as we were for the first night there! Imagine that, with all the hotels there! AND, it was a boy I had a crush on at the time!
When we were at WDW last year, I seemed to keep running into the same few groups of people. I'd struck up a conversation with one woman and later discovered she was staying at the same hotel. My dh just shook his head when we passed each other and said 'hi' and then it occurred again with another person who'd we keep running into. I don't recall their names or anything now, but he just thinks its so typical of me! (He's much more introverted!)
But by far, the most bizarre "Small World" experience I had occurred just last week. Dh and I currently live in Massachusetts; however, we spent the previous 3 years between California and North Dakota. Before that, we both graduated high school in NY. (on a tangent here -- when I first moved to NY, I went to the same school my dh went to for about 2 months, then we switched schools... when we met nearly 3 years later, we figured we shared a class and didn't even realize it!).... anyway... here we were in Massachusetts at my good friends' house (whom I've known for almost 2 years now) who has family here but spent a few years up in Vermont. I've asked her before about when she met her husband, but I was asking again, this time, what year.... but this time she mentioned the year and that she had been dating this wild guy (and she spoke the guys' name) when she first met her husband. My dh and I were in shock and when she repeated the guys' name... we learned that her ex-boyfriend went to high school with my dh and spent many a weekend partying at his house. I had also gotten to know him through my dh! Here we were, strangers.... in a whole different state and both had encounters with this other person in two other different states! "SMALL WORLD!"