5x04 - Tippecanoe and Taylor, Too
Rory and Dean find it increasingly difficult to be alone together due to their distant living arrangement and the fact that he is sharing a car with his estranged wife. Impulsively, Rory asks Dean if he only left Lynsey because she found Rory's letter, and is not completely satisfied with his response. Lorelai and Sookie run Jackson's campaign when he decides to run against Taylor for Town Selectman. Lane tells her band-mate Zach that she has feelings for him.
See you in another life, brother...