people not in CA: ‘september is the start of autumn! it’s so nice, it’s chilly and i can wear sweaters/drink hot beverages while watching the leaves turn red/orange/whatever!’
Yeah I mean I talked about this a bit last night, but it’s absolutely meant to solidify that Crowley is inserting himself in the place of not only Dean’s partner and bestie, but also his brother and his family. Which if we recall last season made Dean livid when Crowley even implied they were like family. But now? Now Dean is living in what I like to call the real Dean Winchesters own personal hell. He’s away from his real family, he’s hurting innocents instead of saving them, he’s without love or real companionship…and imo Crowley being placed in this position is meant to truly drive that point home.