- “This school is my domain and the Franklin is my domain. And don't you ever forget that”
- —Paris to Rory
Rory's first day at Chilton Prep begins badly when Lorelai oversleeps and accompanies her daughter into the intimidating school wearing a t-shirt, cut-off jeans and cowboy boots, an outfit which draws disapproving stares from the other mothers and from her own mother, Emily.
- Lauren Graham as Lorelai Gilmore
- Alexis Bledel as Rory Gilmore
- Melissa McCarthy as Sookie St. James
- Keiko Agena as Lane Kim
- Yanic Truesdale as Michel Gerard
- Scott Patterson as Luke Danes
- Kelly Bishop as Emily Gilmore
- Liz Torres as Miss Patty
- Liza Weil as Paris Geller
- Sally Struthers as Babette Dell
- Alex Borstein as Drella
- Dakin Matthews as Hanlin Charleston
- Chad Michael Murray as Tristan Dugray
- Ted Rooney as Morey Dell
- Shelly Cole as Madeline Lynn
- Teal Redmann as Louise Grant
- Jackson Douglas as Jackson Belleville
- Nick Chinlund as Ian Jack
- John Billingsley as Mr. Remmy
- Roz Witt as Mrs. Traiger
- Carole Goldman as Miss James
- Sean Gunn as Mick
It's Rory's first day at the exclusive prep school Chilton, and Lorelai chooses this day to oversleep. This turns the morning into total chaos because she doesn't have time to pick up her dry cleaning, which means she has nothing to wear. Meanwhile Rory is ranting while Lorelai throws on some old rags in the form of a tight tie-dye shirt and some cutoffs jeans. In short, it looks like Lorelai is heading to the local rodeo. Things go from bad to worse when Rory informs her frazzled mom that they both have to meet the headmaster at Chilton. Since Lorelai has nothing else to wear, she puts on an overcoat and walks out the door. On the way, Lorelai meets a man named Ian, who is the father of another Chilton student. The two get to know each other better and Lorelai tells Ian where she works in case he wants to drop by. When Rory and Lorelai arrive at the headmaster's office, Lorelai's mother, Emily, who just happens to be a close personal friend of the headmaster drops by. Emily makes a big fuss when Lorelai refuses to shed her coat and then regrets her insistence when she gets a load of what Lorelai is wearing. Needless to say, the meeting is quick and awkward with Lorelai stuttering her way through.
After the meeting Rory is now flying solo and gets a lousy initiation into the world of private school. Hanlon, the headmaster, does everything by the book and tells Rory that while she has a good academic record, her social activities are severely lacking. This is because she has enrolled a month late making it extremely hard to catch up. Meanwhile some other Chilton students haven taken a peek at Rory's student file to get the lowdown on her. One of the girls, Paris, is already gearing up to make Rory's life a living hell. Back in Stars Hollow, Lorelai makes it to the coffee shop and has to beg Luke for a cup of java, it's a jumbo coffee kind of morning, and then gets a little lecture from Luke on her inappropriate dress. In class Rory gets a bitter taste of the Chilton academic standards, while Paris answers every single question about Tolstoy's favorite writers and major influences. But a cocky boy named Tristan makes his entrance and gives Rory the once over. At the end of class, Rory gets last week's assignments and the word "daunting" comes to mind. The day keeps getting worse as Paris makes it crystal clear that she is the best student at Chilton. Not only that, but she runs the school paper and will do whatever it takes to keep it that way. Before the next class, Tristan offers to "lend his notes" and he won't stop calling Rory "Mary." What does that mean anyway?
Lorelai finally picks up her clean clothes from the dry cleaner and makes it to work, only to find Ian has arrived and wants to take her to dinner. She is flattered but declines because he is a Chilton dad and that is too close for comfort. As the day goes on, things are getting worse for Rory. She accidentally ruins Paris' homework project when she knocks Paris over as she tries to open her new locker. Paris is steamed and about to get a bad grade when Rory takes the blame and offers to help. Paris refuses, but the teacher forces Paris to take Rory's offer or she'll get a incomplete on the project. Paris begins to feel threatened when Rory starts answering questions that are normally Paris' territory. Paris, on the border of a breakdown, vows to take revenge on Rory. Before Lorelai goes to pick up Rory, she grabs another cup of coffee and tells Luke about her bad day and invitation from Ian. Luke says she did the right thing by declining. When Lorelai finally picks up Rory from school, they do some major commiserating.
- Lorelai – My clothes were at the cleaners and I had the fuzzy clock and it didn't purr on time!
- Luke – It didn't purr?
- Lorelai – It's fuzzy. It purrs.
- Luke – There's no coffee.
- Lorelai – That's not funny.
- Luke – I can give you herbal tea.
- Lorelai – This is not an herbal tea morning. This is a coffee morning.
- Luke – Every morning for you is a coffee morning.
- Lorelai – This is a jumbo coffee morning. I need coffee in an IV.
- Luke – I can give you tea and a Balance bar.
- Lorelai – Please, please, please, tell me you're kidding!
- Luke – I'm kidding.
- Lorelai – You're sick.
- Luke – Yup.
- Lorelai – You're a sadist, you're a fiend! (Luke brings her coffee) You're pretty.
- Lorelai – Do you want me to talk to anybody? A parent, a teacher, a big guy named Moose?
- The "Welcome to Stars Hollow" sign shows a population of 9,973.
- In this episode, Sean Gunn plays a character named "Mick". In the rest of the series, Sean Gunn plays "Kirk".
- Please note that this episode should not be confused with The Lorelais' First Day at Yale, which is the second episode of Season 4.
- "I'm the Man Who Murdered Love" by XTC
- "I Don't Know How to Say Goodbye to You" by Sam Phillips
- "Stars and Stripes Forever" by John Phillip Sousa
- Harry Potter
- War and Peace, by Leo Tolstoy
- Anna Karenina, by Leo Tolstoy
- David Copperfield, by Charles Dickens
- Great Expectations, by Charles Dickens
- A Tale of Two Cities, by Charles Dickens
- Little Dorrit, by Charles Dickens
- George Sand
- Lane – You guys! XTC. Apple Venus Volume 2.
- Headmaster Charleston – What are your aspirations?
- Rory – I want to go to Harvard and study journalism and political science.
- Headmaster – On your way to being…?
- Rory – Christiane Amanpour.
- Headmaster – Really?
- Rory – Yes.
- Headmaster – Not Cokie Roberts.
- Rory – No.
- Headmaster – Not Oprah, Rosie, or one of the women from The View?
- Rory – No.
- Lorelai – I was supposed to look together and fabulous and not like I'd been up all night playing quarters!
- Drella – Hey, do I look like I have Panasonic stamped on my ass?
- Miss Patty (to her students) – 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.