It wouldn't be the diagnosis that Niles would make, but if asked, he would be forced to admit that some of his own positive sentimental feelings were potentially being displaced on Winchester, too, if his own schmoopiness was taken into account.

He smiles genuinely, honestly intrigued by the sharp mind he'd encountered by chance (or as close to change as he can imagine considering how fabricated this experience was said to be).

"You know, I appreciate you saying that very much, thank you. The feeling's mutual, Dean." He leans in a little, an excited little smile on his face. "Honestly, I should be thanking you. You've proven to be quite the guide. Should I ever use my new knowledge of Peter Parker and Spider-Man, I'll be sure to credit you."