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.

Rory asks Dean to accompany her to a formal dance at Chilton, but the lovely evening is spoiled when they fall asleep together after the dance.

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.

Lorelai becomes increasingly serious about Max. Luke's girlfriend accuses him of being in love with Lorelai, and Rory attempts to win Dean back.

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.