Season synopsis
Contains spoilers for this season and earlier seasons.
Lorelai begins the season weighing Max’s proposal and accepts it after talking with Rory. As the wedding approaches, Lorelai panics during her bachelorette party, leaves town with Rory and calls it off; on their Harvard road trip she admits she did not really love Max. Christopher returns with Sherry, a new partner who appears ready for a settled life, leaving Lorelai to reconsider whether the family she once imagined with Rory’s father is possible.
Luke’s troubled teenage nephew Jess arrives in Stars Hollow and quickly draws Rory’s attention, although she is still dating Dean. Jess and Rory become friends, and their closeness fuels arguments between Rory and Dean and tension between Lorelai and Luke. After Rory and Jess crash the car Dean rebuilt for her, Rory fractures her wrist and Jess returns to New York. Later Rory travels there to see him, missing Lorelai’s business-school graduation. Jess returns for Sookie and Jackson’s wedding, where Rory kisses him while still with Dean.
Around them, the town and the Gilmore family keep shifting. Jackson proposes to Sookie after winning their picnic-basket date, and the season ends at their wedding. Richard, unhappy in retirement after resigning from his firm, starts an insurance consultancy; Paris becomes editor of the Chilton paper, while Lane joins the cheerleaders and decides she wants to play drums. On the eve of Sookie’s wedding, Lorelai sleeps with Christopher, but he leaves when he learns Sherry is pregnant. Rory and Lorelai walk into the ceremony uncertain about what comes next.