When Rory is accepted to attend a prestigious prep school, Lorelai must swallow her pride and ask her wealthy parents for help paying the tuition.

Rory's first day at Chilton doesn't go smoothly: First, Lorelai's attire offends Emily and the headmaster; then Rory meets some obnoxious classmates.

When Rory and Richard bond during a day of golf at the club, Lorelai feels jealous of Rory's deepening connection with her grandparents.

After Rory receives a bad grade on her English paper, Lorelai helps her cram for a big Shakespeare exam – but catastrophe strikes on test day.