Skye and Dean have been best friends since they were kids. John Winchester took her with him and his family after a hunt gone wrong with John Winchester and Skye's Parents. Years later Skye still has been by Dean's side slowly falling for him. Sure she get's jealous when he is always having his one night stands and flirting with women but she can't help it cause she is scared of losing him. She tries to put her feelings aside because they have bigger things to deal with and that's to find John Winchester.