Gilmore Girls: 10 Of The Most Dramatic Things That Happened At Chilton

In the opening episode of Gilmore Girls, Rory and Lorelai are excited when they learn about Rory’s acceptance to Chilton — a private high school with a prestigious background. Rory was hesitant about going to a new school after meeting Dean but it was the right move for her journey. Not only did Chilton help her get into Yale, but it also introduced her to a group of characters that would be apart of her life forever. 

But like every show that’s based in high school, the drama was inevitable. Rory had issues with her grades, classmates, boys, her mom dating her teacher… Chilton was not a dull place to get an education. 

10 Rory’s First Dance

In “Rory’s Dance,” Chilton is having a school dance and Rory was unsure if she should go or not. She was still the new girl in school and didn’t get along with most of her classmates. And let’s not forget that Tristan was harassing her about the dance every chance he had. Rory ended up going to the dance and bringing Dean as her date.

The drama began when Rory and Dean had to have the “are we or aren’t we?” conversation revolving around their relationship. Were they dating or not? After Tristan made cruel remarks over the two, Dean defended Rory’s honor and the two got into a physical altercation. Dean came out victorious and won Rory’s heart but it was quite the drama.

9 Paris Saw Rory’s Mom Kiss Their Teacher

Max and Lorelai took their relationship slowly when they realized they were both interested in each other. They both knew how inappropriate it was to be dating each other because of Rory. But once Rory found out that her mom and teacher were dating on the down-low, she had no choice but to accept it and move forward. Rory began to like Max and the idea of him and her mom together.

Shockingly, Lorelai didn’t like that Rory was falling for Max as a step-father figure. But just as she was planning on breaking up with Max at the parent-teacher day at Chilton, the two locked lips inside the classroom. Unbeknownst to them both, Paris saw the kiss and told the whole school. Max was in hot water afterward and Rory was embarrassed.

8 When Rory Was Late For Her Exam

When Rory gets a bad grade on a paper, she overdoes it studying and wakes up late on the day of an exam. Lorelai told Rory to take her car to make up time but becomes even later when a deer hits her car.

Rory walked into her classroom too late to take the exam and has a meltdown in front of everyone. She yells at Mr. Medina, scolds Paris, and warns Tristan to stop calling her Mary.

7 The Puffs

When Headmaster Charleston warns Rory that she’s segregating herself from other classmates of hers, she goes out of her way to be friendly to girls in the cafeteria. Rory had no idea that the girls she sat down with were apart of a secret club called The Puffs. Paris gave Rory a lowdown on the Puffs’ history and how prestigious it was to be apart of their group.

One night, the Puffs “kidnapped” Rory and Paris to haze parts of Chilton, but their little game failed when they were caught and reprimanded by Headmaster Charleston. Rory made sure to rip into him for suggesting she make new friends.

6 Her First Day At School Was One For The Books

Rory and Lorelai aren’t the most punctual women but they organize themselves when the situation calls for it. Lorelai, however, failed to get her ducks in a row on the morning of Rory’s first day of school.

The women were already running late and Lorelai had nothing to wear. All of her nice clothes were at the dry cleaners, which meant she had to drop Rory off at school in cowboy boots, ripped denim shorts, and a tye-die shirt. The drama only continued when Lorelai had to walk Rory into the school.

5 The Franklin

The Franklin was Chilton’s student newspaper, which both Rory and Paris were members of. Paris became the editor in charge when the girls were juniors.

Rory was a writer for the Franklin and was often given boring stories to cover because Paris didn’t respect Rory’s talents. Things get worse at the Franklin when Paris finds out that Rory encouraged Tristan to ask Paris out on a date. Paris then took things out on Rory, like telling her the wrong times for their meetings and trying to get her off the paper.

4 When Paris Was Denied By Harvard

In the episode “The Big One,” Rory and Paris are chosen to speak at Chilton’s bicentennial. The two women were annoyed with each other as it was but things got worse on the day of the speech.

Paris was late for the bicentennial and when she showed up, she was a little worse for wear. That morning, Paris found out that she was denied from Harvard. The sheer thought of all her hard work going to waste was devastating. She showed up to the event in her sweats and unkempt hair and told everyone that she didn’t get into Harvard. She even brought up her sex life during her rant! Rory had to take her off stage to save her.

3 Paris & Rory As a Team

In A Year in the Life’s episode “Spring,” Rory and Paris go back to Chilton for Alumni Day. They’re greeted by Headmaster Charleston and see other familiar faces like Francie and “Tristan” (who was not played by Chad Michael Murray). Once Paris sees Tristan talking to another woman, she panics and runs into the bathroom where she has a panic attack.

It’s then—in the midst of her own divorce—that she realizes she was still in love with Tristan and couldn’t face him. Rory had to talk Paris off a ledge and convince her to come out.

2 When Dean And Rory Got Back Together (The First Time)

When Dean gifts Rory a car and tells her he loves her, Rory is in shock. She’s speechless and needed some time to think. Dean, however, took her silence as she didn’t love him and the two broke up. As time went by, Rory realized she did love him and dropped hints to him during the town hall meeting.

In a final plea, Dean showed up at Chilton and begged for answers. Rory finally told him that she loved him too and they got back together.

1 Jess’s Mystery Call

At Rory’s graduation from Chilton, everyone that mattered to Rory was there for her — except Jess. Jess fled town without a thoughtful goodbye or explanation. But on the day of Rory’s graduation, she kept getting phantom phone calls with no one on the other line.

Rory knew in her heart that it was Jess on the other line and lashed out at him. She told him to stop calling her and that she probably loved him but she would never know because she was moving on in life. She was going to Europe that summer and then would be at Yale in the fall. She didn’t have time for Jess’s games. It was a pivotal moment for Rory that happened in Chilton’s halls.

About The Author

Lynn Gibbs
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Lynn is a nomad who travels the globe on the hunt for her next adventure with her husband. A lover of being outside (and finding the best latte in town), Lynn is typically hiking, walking, or jogging when she’s not focusing on her love of writing. When it comes to shows streaming on Netflix or anything Bravo-related, Lynn’s your gal.

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