The first time Dean wanted to tell her, they were in the library of the Bunker, researching poltergeists for their next case. It was just him and her in that large room - Sammy had turned in for the night a while back. Dean/OC (Reader)

"We have to get going if we want to gank this demon." She heard Dean call from the library. She was in her room, looking over the dress that she was not looking forward to wearing. She groaned as she slipped on the black dress. At least she was the one to pick out her dress. Some of the choices that the boys - ahem, Dean Winchester - had picked out just horrified her. TFW Imagine.

Imagine having an intimate moment with Dean and Sam walks in on you two. Dea/ OC (Reader) It had been three weeks. Three very long weeks without the Winchester brothers - mainly without Dean. Sure she had Kevin at the Bunker with her, but he didn't really leave the tablet in his room and only came out of his hibernation when she forced him to eat something.

Dean Winchester has always been a bit of a thorn in Kelsey's side - a very attractive thorn, but still... A visit at her uncle Bobby's reunites her with the boys, and she begins having vivid dreams - about Dean. Is it just her subconscious trying to tell her something? Or is there more to it than that?

Imagine trying to get Dean into more recent music but he says he hates it, but you find him a few days later humming the songs around the Bunker