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.

Lorelai tries to break up with Rory's teacher Max, on parent-teacher night, which leads to more problems for her daughter at school.

Though Lorelai is excited about going to a Bangles concert, she offers the four concert tickets to Rory and three of her new schoolmates.

Rory waits for acceptance letters from colleges; Lorelai shares a passionate kiss with ex-fiance Max and wonders if ending the engagement was the right decision.

Newly retired Richard is making Emily crazy, so Lorelai agrees to take her father for a day in Stars Hollow, where he proceeds to annoy both Lorelai and Rory.