S5, E4: Rory and Dean have difficulty meeting alone because they live far apart and Dean (recurring guest star JARED PADALECKI) shares a car with his estranged wife. Impulsively, Rory asks Dean if he left his wife because Lindsay found Rory's letter--and she is not completely satisfied with his response. Lorelai and Sookie manage Jackson's (recurring guest star JACKSON DOUGLAS) campaign when he decides to compete against Taylor (recurring guest star MICHAEL WINTERS) for town selectman. Lane tells her band mate Zach (recurring guest star TODD LOWE) that she has feelings for him.