This made me imagine an entire episode of Rowena and Castiel stealing the impala to go on a joyride while they talk shit about the Bros.
Rowena confesses that time she hooked up with Sam when they were chasing Lucifer. Cas only says honest nice things about Dean and their friendship. Rowena then insists on making Cas confess his crush on Dean. Making Cas disclose his numerous hookups with Dean before every apocalypse they fought. And how after everything and everyone was saved, Dean just never talked about it or just brushed it up as impulsive moments that only accentuate the brohood between Dean and him.
Rowena at first laughed and made fun of Cas, because he honestly believed this, and was happy just to have Dean as his friend and close enough to fight the next apocalypse. Eventually, their trip becomes more honest confessions and perspectives about humans and love. Rowena gets angry with Dean for treating Cas this way and never owning their relationship.
So the future queen of hell convinces Cas to go to a gay bar and have some drinks and dance. Then she takes several pictures of Cas with very hot dudes and sends them to Dean with the following message:
“I have taken your baby for a spin around the block, if you want to recover the thing you love the most, you better say the blue eye sweetie to come to your arms tonight and officially invite him to your bed not only for one night. And then I will consider returning your car. ;)”