Dean's boyfriends ranked by how normal they were about him (from most to least):
4. Lee Webb. As normal as one could get about Dean Winchester. Like yeah, he tried to kill him, but that was completely unrelated to them being exes. Even able to have a nice, friendly reunion with Dean, no hard feelings at all (again, until Lee tried to kill him).
3. Benny Lafitte. Genuinely probably the closest Dean got to a normal relationship with a man and they probably could have made it work if they weren't both hung up on other people. Benny did end up sacrificing his life for Dean, after Dean ghosted him even, but Dean was only partly the motivation there. Still, seeing the dynamic between Dean and Cas in Purgatory and willingly inserting yourself is kind of bonkers.
2. Crowley. Man started this relationship thinking he had the upper hand, then caught feelings and fully shattered himself on the altar of Dean Winchester. Went around telling people that Dean completes him after they had a regrettable summer fling, then sacrificed his life for him because that's just what falling in love with late-seasons Dean does to a motherfucker.
(Special mention of Chuck, who while completely abnormal about Dean was never his boyfriend, as much as he wishes.)
1. Castiel. And it's not even close. In this competition, Cas takes the gold, silver and bronze. Laid a hand on Dean in hell and never had a normal thought again. You just know he had fantasies for years about confessing his love for Dean while dying in his arms before it actually happened. Fortunately for him, Dean matches his freak perfectly.
