Just so you guys know, I'm crying with laughter over this whole thread.
I'm going to say the RBY and GSC games are tied for creepiest, for these reasons: Lavender Town and the Ruins of Alph. I used to hop on my bike and ride through Lavender Town as fast as I could so I didn't have to stay there so long (and I was very reluctant to go there for the story), and the first time I went to the Ruins of Alph I was there for about five seconds before I went "Nope" and bravely ran away. I didn't return until I beat the Elite Four and had half a dozen powerhouses to protect me.![]()