I'm not much of an adventurous eater, but my parents have a few that have always baffled me:
My dad likes to pour sugar on his pancakes to make them crunchy. Don't they already make crunchy pancakes? And call them waffles?
My mom tells of her mother making something called "Bread on Top of Plate." If I remember correctly, it went something like this: take a slice of white bread - on a plate of course, spread butter on it (optional), pour enough sugar on top to cover the bread, and pour milk over the whole think. I used to tell her it should have been called "Milk on Top of Bread."