(Y/N) has a huge crush on Sam Winchester, and when he falls into the pit, you are heartbroken... only to have him come back soulless... So he constantly flirts with you and you have to keep telling him no.
Dean sold his life to save Sam and now, he's going to hell. Meeting you wasn't supposed to happen but it did and now he needs to make the best of his time on Earth.
Life had damaged you just as much as it had damaged him and when two broken people try to fix each other, it's called love. True love