This episode originally aired on October 12, 2000 on The WB
Gilmore Girls second episode opens with Lorelai and Rory scrambling to get ready for Rory’s first day at the prestigious Chilton Preparatory School. However, Lorelai’s laundry is held hostage by a neighbor, causing her to wear an inappropriate outfit that consists of a tie-dyed t-shirt, cutoff shorts, and cowboy boots to Chilton.
Upon arriving at Chilton, both Lorelai and Rory face challenges. Rory meets Paris Geller, a driven and competitive classmate, who views her as a threat. Paris, along with her friends Madeline and Louise, makes it quite clear that she’s determined to be the top of her class, and she perceives Rory’s academic prowess as a direct challenge.
Rory’s first day also brings her face to face with Tristan, a boy who annoyingly calls her “Mary”, hinting at her innocent appearance. He is another thorn in Rory’s side, as he seems to enjoy getting under her skin.
Lorelai, on the other hand, faces her own set of challenges. The headmaster, Charleston, is not too pleased with her attire and hints at the importance of parents’ involvement in school activities. Moreover, she has an awkward encounter with Emily, her mother, at a parent-teacher meeting, highlighting the tension and differences between them.
Back in Stars Hollow, Lorelai vents to Sookie about her disastrous day, and Sookie tries to provide comfort by jokingly offering to stalk Tristan for Rory.
At the end of Rory’s school day, she returns home, overwhelmed and disheartened by the hostile environment. She considers not returning to Chilton, doubting whether she can fit in. However, after a heart-to-heart with Lorelai, she decides to stick it out, proving her determination to reach her goal of attending Harvard.
Memorable quotes from the episode: