Teal Redmann

Rory's first day at Chilton Prep begins badly when Lorelai accompanies her daughter into the intimidating school wearing a T-shirt, cut-off jeans and cowboy boots, an outfit that draws disapproving stares from the other mothers.

Still struggling to catch up at Chilton, Rory receives the first 'D' of her life on an English assignment and is so humiliated that she plunges into obsessive studying.

While the whole town is busy making arrangements for Lorelai and Max's wedding, Lorelai finally tells Emily that she's getting married and is hurt by her mother's disinterested reaction.

Luke takes in his wild 17-year-old nephew Jess, ignoring Lorelai's well-intentioned advice and Rory is drawn to the new guy in town.

Rory runs to her grandparents' house after discovering Lorelai and Max are dating again, and Lorelai discovers the truth behind Dean and Rory's breakup.

Rory's great-grandmother offers Lorelai a trust fund for Rory's education, causing Emily to fear losing her newfound relationship with them.