Never Have I Ever by sweetdean
Summary: When Jo drags Dean along to a game of “never have I ever” with her friends, he finds himself getting caught up in a lot more than just a game.
“Never have I ever hung out with such an asshole,” Dean countered, positively shocked at his own sass. Cas smirked again.
“Oh, are we hanging out now?”
Comments: 9/10. Fluffy but also quite angsty in the middle. They meet in high school, Cas is a mess but Dean helps him get his life together. But Dean has to leave for college, while Cas wants to travel. So they go their separate ways, not before Cas breaks his heart though. A year later they reunite. There’s some pretty angsty parts about their separation and how they deal with it, but there are some seriously sappy and romantic and fluffy moments in the fic. I love the ending, so sappy and domestic. I’m a little alarmed by the very brief prep in this fic. It seems realistic but also unrealistic at the same time, sometimes they are innocent high school kids, but other times they seem wise beyond their years. I love it though.