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Summary
The events of the supernatural have happened a couple of years in the past now. While Castiel has been alive and still tending to his duties in heaven, he occasionally comes down to come and visit Dean and Sam. Despite the confession Castiel made before his departure, things have felt a bit stifled between the two.
Feelings go unacknowledged once again, Dean not really knowing how to approach the situation, tries to bring a more subtle approach and take Castiel on his closet approximation of a date he can. He’s slept with a lot of people, done the deed, done the aftercar,e and all that jazz. But dating someone for him came way less often, especially a ( male adjacent ) person such as Castiel. And this on top of the fact that he’s never admitted he’s bisexual.
So hijinks ensue, and Dean comes up with ideas from the internet,d old TV shows, and movies to try and find a way to convey his feelings without actually doing that. Which is totally going to go well.