Season 4 marks a year of transitions for the Gilmores. Lorelai quits her job as manager of the Independence Inn, realizing her ambition of opening an inn of her own, The Dragonfly, with her best friend, Sookie (Melissa McCarthy, Samantha Who?). But various setbacks make renovating the new inn harder than Lorelai could have imagined. Lorelai and Sookie start a catering business to help pay for the expenses, made all the more difficult because Sookie is pregnant.
Meanwhile, Rory is adjusting to her new life at Yale University, coping with the trials and tribulations that come with living at college. The stress of academia is bundled with having to handle her eccentric fellow students, especially her roommates, and the pressure of achieving her dream of becoming a journalist.
All the while, the Gilmore girls still have to deal with Lorelai's parents every Friday night, the men of love lives past, and the relationships of those who come in and out of Stars Hollow.