I don't really know what I like about it, honestly xD. I hadn't thought about it much. But I guess I remember it starting from reading an one-shot on here years ago that was Gary/Misty, and I thought it was sweet. Can't recall what it's called anymore, though, except that I believe it's from a rather well-known writer at the time--but I can't think of her name, either.
Yeah, I fear Amourshipping as well, if only because if it becomes canon, it would seem hypocritical on the writers to make Ash oblivious to any kinds of romance. But yeah, I see where you're coming from. Still, that's why we're asked to put down five of our favorite Pokémon pairings, and non-Pokémon pairings.
Not a fan of "sexy" Santa outfits, personally, but it depends on how it's presented in which I may find the idea sweet.