In Season 5 of the Emmy-winning series, Lorelai and Rory face major life changes. Lorelai is happy owning and operating an inn with best friend Sookie, but quickly learns the demands of being the boss. A bigger surprise is that her longtime friendship with Luke has become a romance. Lorelai and Luke try to hide their relationship, but the town soon knows they are dating. The reappearance of Rory's father, Christopher (recurring guest star David Sutcliffe), adds to the drama. Rory's romantic life is also complicated; at the forefront is her relationship with Dean (recurring guest star Jared Padalecki, Supernatural) — who's now married. In her second year at Yale, Rory is more involved in the college newspaper, and meets Logan (recurring guest star Matt Czuchry, The Good Wife), who comes from the same old-money world as her grandparents. Rory could be on the path of her dreams — or is she? Notable guest stars this season include Norman Mailer, Michael DeLuise, and Carole King.