S3, E21: Jess leaves Stars Hollow and travels across the country to Venice, California, where his father, Jimmy (recurring guest star ROB ESTES), lives. The reunion and the important decisions it engenders cause tension with Jimmy's live-in girlfriend, Sasha (SHERILYN FENN - "Twin Peaks," "Boxing Helena"). Meanwhile, although she has an almost impossible amount of school-related work to complete before graduation, Rory agrees to help her grandmother choose an outfit for the ceremony--resulting in another conflict with Lorelai. Also, Lorelai agonizes over paying for Rory's Yale education.