I love Cain too and could totally see a prof au for them. Just I can see Cain being this wise older lover that knows it won’t last but is all about the campsite rule. So Dean ends up always looking back on the relationship fondly.

I can definitely see that. I also really liked the idea of it being one of those nostalgic relationships one looks back on fondly. The timing is all wrong for something permanent, but it’s good while it lasts and Dean learns a lot about himself and life and relationships while it lasts. It’s bittersweet and I like that a lot. (I’m such a sucker for that kind of thing.)
Esp if they run into each other later in life and Dean’s established and has his own life going and they just reminisce over a beer or two.
*wistful sigh*