"The Lorelais’ First Day at Chilton"
Written by Amy Sherman-Palladino; directed by Arlene Sanford

Lorelai paints Rory’s toenails on their porch as Rory eats whipped cream. Lorelai explains that she’s painting Rory’s nails red because “everybody knows that private school girls are bad, and bad girls always wear red nail polish.” Lane arrives with a new CD and Lorelai quits halfway through her painting job, noting that Rory will be wearing shoes anyway. The next morning, Rory wakes Lorelai up at 7:10, though Lorelai thinks it’s only 5:45, because that’s when she wanted her alarm to go off. Rory hounds Lorelai to get out of the house, but Lorelai runs into problems with finding clean clothes. She winds up in a pink tie-dyed shirt, short cut-offs, and cowboy boots. The two arrive at Chilton, where they realize that the school looks a lot more imposing than they remember it. Rory begs Lorelai to go in with her to meet the headmaster, but Lorelai tries to beg off because of the way she’s dressed. They run into another single parent named Ian, who seems to be interested in Lorelai, and Rory has to pull her away so she won’t be late. The two finally meet with Headmaster Charleston (Dakin Matthews) and realize that Emily is already there, since she, Richard, and the headmaster are old friends. Emily makes Lorelai take off her coat, revealing her embarrassing outfit. After they leave the office, Emily chastises Lorelai for making a bad impression, then tells her that she came to put in a good word and support Rory.

Headmaster Charleston looks over Rory’s records and notes that, though she has excellent academic achievements, she doesn’t have as much in the way of her social life. Rory announces that she wants to be a journalist like Christiane Amanpour; Headmaster Charleston questions her motivations. He warns that though she may have been the smartest girl at her old school, Chilton is much harder to achieve in, and she’ll have an especially hard time, since she’s not starting the semester with everyone else. He makes it clear to her that failure will not be acceptable. As Rory fills out forms in the administration office, Paris Geller (Liza Weil), Louise Grant (Teal Redmann), and Madeline Lynn (Shelly Cole) lift her file to see if she’ll be any competition. Paris shrugs off the possibility of Rory wanting to join the newspaper staff and brags that she’ll never catch up, since she’s already behind. Lorelai heads to Luke’s, where Luke tries to convince her that there’s no coffee, a joke she doesn’t find funny. She fills him in on her horrible morning, but he’s not very sympathetic. Lorelai passes Miss Patty’s studio and gets questioned about her outfit again. Emily calls Lorelai at home about clothes for Rory; Lorelai tries to get her to back off of her Chilton madness. At school, Paris proves to be the smartest, most ambitious student in class and Tristan Dugray (Chad Michael Murray) appears to be the least. He takes a quick interest in Rory, branding her a “Mary.”

After class, Paris corners Rory to ask if she’s planning to try to get on the staff of the school newspaper, The Franklin. She makes it clear that she’s first in the class and plans to keep her spot, so Rory shouldn’t try to show her up. At the Independence Inn, Sookie accepts produce from the inn’s produce guy Jackson Bellville (Jackson Douglas). Lorelai shows up looking the way she’d wanted to that morning and laments that everyone saw her making a fool of herself. Emily calls Lorelai again to announce that she’s bought Rory a parking spot at Chilton. Lorelai points out that Rory doesn’t have a car and Emily replies that they’ll buy her one for her birthday. At Chilton, Rory encounters Tristan, who calls her Mary and offers to loan her notes. Lorelai mediates between people involved in a fender bender at the inn and gets a visit from Ian, who asks her out. Lorelai turns him down, but he tells her he’ll try again when he returns from a business trip. At school, Rory struggles with her locker, accidentally knocking into Paris and destroying a project she was about to turn in. They wind up in the same class, where Paris has to accept an incomplete for not having her project. Rory tells the teacher that she’s to blame and the teacher assigns her to help her redo it. Paris refuses to let her help, so the teacher relents and tells Paris to do it herself. The rest of the class greets Rory and Tristan calls her Mary again.

Lorelai heads back to Luke’s for more coffee and tells him that Ian asked her out. Luke tells her that it’s good that she turned Ian down. She shirks his no cell phone rule to answer a call from her neighbor Babette Dell (Sally Struthers), then hurries home to meet up with Babette and her husband Morey (Ted Rooney). Babette and Morey have noticed men around Lorelai’s house; the men announce that they’re there to install a DSL line. Emily called them and placed the order, telling them to look for the spare key under a ceramic frog. Frustrated by her mother’s meddling, Lorelai cancels the order. At school, Rory passes Paris a note of apology but Paris isn’t having any of it. Rory starts showing her up in class, and afterwards, Paris warns her not to mess with her. Tristan again calls Rory “Mary,” much to her annoyance. Lorelai tracks Emily down at a salon and announces that she wants her to stop buying things for Rory. Lorelai picks Rory up at school and they lament their bad days together. Rory mentions that Tristan keeps calling her Mary; Lorelai explains that it’s because they think she’s a goody-goody and want to compare her to the Virgin Mary. That night, the two eat pizza with Lane, who’s sad because Rory isn’t at her school anymore. Lane heads home and Rory wonders how she can get Paris on her good side. Outside the diner, they discuss Luke; Rory warns Lorelai never to date him, because if they break up, they won’t be able to eat there. Lorelai assures her that that will never happen.

WELCOME TO STARS HOLLOW: Headmaster Charleston, Paris, Louise, Madeline, Tristan, Jackson, Babette, Morey

MEMORABLE QUOTES: Lorelai: “You’re sick.”
Luke: “Yup.”
Lorelai: “You’re a sadist, you’re a fiend!” (He brings her coffee) “You’re pretty.”

“Now, walk smooth. That’s the new Harry Potter on your heads. If they should drop, Harry will die, and there won’t be any more books.” - Miss Patty to dancers walking with books on their heads

“Wow, Biblical insults. This is an advanced school.” - Rory

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