Gilmore Girls Re-Watch: The Lorelais’ First Day at Chilton (Season 1 Episode 2)

There’s really no better show to binge-watch than Gilmore Girls. I’ve probably seen every episode at least twenty times, and it never gets old.

“The Lorelais’ First Day at Chilton,” (Season 1, Episode 2) continues to set the scene of Gilmore Girls and to establish its characters and major themes. The night before Rory’s first day at Chilton, Lorelai sits outside with her, painting her toenails red. Rory questions the choice, especially since she’s going to be wearing shoes anyway. Lorelai’s response is that private school girls are “bad” and bad girls wear red nail polish, obviously! This short scene continues to set up the role reversal between Lorelai and Rory. Rory is the responsible adult (most of the time) in their relationship, while Lorelai is more flighty and whimsical. Of course, she does take on her mothering role when it counts the most—like making sure Rory goes to the new school and gets the education she deserves.

Furthering that dynamic in an almost unbelievable way, Lorelai oversleeps the next morning. Rory is up and ready to go, and wakes up her mother who overslept because her new, furry alarm clock didn’t purr. And what says Lorelai more than a furry alarm clock that purrs?

To make matters worse, Lorelai had planned to pick up her laundry that morning from the cleaners, and now she doesn’t have time. So she’s forced to wear the only outfit she can put together: a pink, tie-dyed to and a bad pair of cut-off, jean shorts. She looks ridiculous; but hey, at least she gets Rory to school on time!

Their arrival to Chilton also continues to establish the relationship between Lorelai and her mother, since Emily is waiting for them in Headmaster Charleston’s office when they arrive. Turns out Emily is friends with Headmaster Charleston’s wife, and Emily wants to be there for Rory on her first day. It’s not entirely inappropriate, but it makes Lorelai feel threatened – and this isn’t the first time. Lorelai will continue to stake a certain claim over her relationship with her daughter, even when she shouldn’t. And one of Lorelai’s most significant struggles throughout the series is her pride, which we already saw her have to swallow in the pilot episode.

In more of Emily’s failed attempts to help, she buys Rory a parking space (even though Rory doesn’t have a car), asks Lorelai for Rory’s size so she can buy her extra Chilton uniforms and accessories, and orders DSL. Lorelai refuses all of this, insisting on being the sole provider – other than that whole. Chilton tuition thing.

Lorelai: We like our internet slow, okay? We can turn it on, walk around, do a little dance, make a sandwich. With DSL, there’s no dancing, no walking, and we’d starve! It’d be all work and no play. Have you not seen The Shining, mom?”

This episode of Gilmore Girls also introduces more of the supporting cast who help to make this show so special. Paris steals Rory’s file an immediately pegs her as competition before she’s even had a class with her. Jackson tries to sell peaches to Sookie, who tests them in every crazy way she can think of, including rolling them on the floor. Babette and Maury are introduced as Lorelai’s crazy neighbors, who call Lorelai about the men setting up DSL outside her house. Of course, high on their list of concerns is the fact that the men kicked over one of their gnomes.

And finally, Kirk (Sean Gunn) is introduced as one of the DSL workers. But in this episode, he introduces himself as “Mick,” and he’s someone that Lorelai has never seen before. Only later will he become the quirky and beloved character of Kirk, who holds nearly every job available in the town of Stars Hollow.

Perhaps the most important dynamic that’s established in “The Lorelais’ First Day of Chilton,” though, is a bit of foreshadowing on Lorelai’s relationship with Luke. They continue their running joke about Lorelai’s coffee addiction, but Lorelai also shares the details of her day with Luke as she orders her coffee. Those details include Lorelai turning down a “Chilton Dad” for a date, and Luke revealing just a tiny glimmer of jealousy as she talks about the man.

At the end of the episode, Lorelai asks Rory what she thinks of Luke:

Lorelai: Hey, what do you think of Luke?
Rory: What do you mean?
Lorelai: I mean, do you think he’s cute?
Rory: Oh, no. No way.
Lorelai: No way, what?
Rory: You cannot date Luke.
Lorelai: I said nothing about dating Luke.
Rory: If you date him, you’ll break up, and we’ll never be able to eat there again.

Not only is it significant that Lorelai is willing to have such conversations with her daughter, but it also becomes more obvious that the driving romantic relationship behind this show is that of Lorelai and Luke.

This show does a great job with its final shots, by the way. As Lorelai and Rory continue their conversation, the camera pans out to show Luke watching them from the diner as he closes up for the night.

You can watch this episode of Gilmore Girls online here:
The Lorelais’ First Day at Chilton 

Are you re-watching Gilmore Girls like me, or are you seeing it now for the very first time? Leave a comment and share your thoughts on “The Lorelais’ First Day of Chilton,” or, share your all-time favorite episode of Gilmore Girls below.