Fans of Gilmore Girls are introduced to Chilton right away, as, in the first episode, Lorelai shares with Sookie that Rory has been accepted to this esteemed private school. As soon as Rory starts attending, she realizes that it's a much more intense place than she ever anticipated and that she might have to work harder than she ever has before in order to survive on an academic and social level.
Chilton is an intimidating and interesting school, but it's also the perfect place for Rory to come of age, grow up, and learn some important lessons. From her struggles to her triumphs, she experiences a lot at Chilton and leaves a much better person than she was before.
10 Hard Work Is Always Rewarded
Fans have some issues with Rory, including her strange obsession with her "studying tree," but, from seasons one to three, Rory learns a big lesson at Chilton: that hard work is always rewarded.
While Rory struggles at first, as she has trouble catching up before an important English test. Yet, she keeps at it and ultimately impresses her teacher and wins the respect of her fellow students. It would have been impossible for anyone to memorize so many facts and dates before that test, so it's definitely not indicative of Rory's intelligence or skills. Rory excels in her classes from then on and eventually goes on to be valedictorian.
9 Competition Can Be Friendly But Also Toxic
It's easy to think of Rory and Paris as characters who hate each other, as Paris wants to be the Queen Bee of Chilton and she doesn't want Rory getting higher grades. Over time, they form a friendship that viewers cherish.
Rory learns another lesson from her time at Chilton that has to do with Paris: sometimes competition can be friendly and helpful, and, at other times, it's totally toxic. There are moments when Paris pushes Rory to try harder and be more confident, which is a positive thing. But, in other episodes, like when Paris takes over a group project, Rory realizes that it's best to focus on her own path.
8 It's A Good Idea To Get Involved
Rory isn't someone who could be considered a joiner, and she hates team sports and groups of any kind. While it seems like Chilton might have some clubs that would appeal to her, she tends to keep to herself.
That is, until the school lets her know that she has to get involved, and then Rory tries her best, even attempting to join the secret society The Puffs until everyone gets into trouble. Rory learns that, while it's not always easy or fun, it's better to attempt to have a social life at school than to be alone. She also attends Chilton's dance when she starts dating Dean and actually has fun.
7 She Isn't Always The Smartest Person In The Room
Both Rory and Paris are used to being the most intelligent person in whatever room they're in, and they each rule Stars Hollow High and Chilton. They think that no one else can get higher grades or be more beloved by the teachers.
That all changes when Rory starts attending Chilton, and she realizes that Paris is just as smart as she is. While they both do well and Rory isn't as much of a threat to Paris as she originally seems, it's still good for Rory to realize that other people have a lot to offer at school.
6 Challenge Assumptions And Expectations
In the season three episode "Application Anxiety," Chilton holds a seminar on getting accepted to college, and Rory learns that everything she thought is totally wrong.
Rory can't just write an essay about how inspiring Hilary Chilton is and expect to get into Harvard, as it turns out that's the most popular topic. She also realizes that she has competition, as every applicant has stellar grades, but they have more extra-curricular interests than she does. Rory learns that she can't make assumptions and that nothing in life goes as expected. She does get into three Ivy Leagues, but she has to hustle a bit more than she anticipated in order to make it happen.
5 Keep Stress Levels Down
Gilmore Girls viewers don't love the season three scene when Paris shares with the school that she had sex with Jamie and she has a breakdown. It's an odd way to treat this situation, as Paris and Jamie have been together for a while. But, besides this problematic moment, this storyline has a good lesson about stress.
Paris lets her stress over getting into Harvard get the best of her, and she gets so upset that she hides at home and wonders if she's a failure. Rory is there for Paris, and she also learns the lesson that keeping stress at bay is important. Getting overwhelmed is inevitable, but life is always going to be tough and throw curveballs. It seems like Paris doesn't have a self-care routine or any outlets to stay calm.
4 It Doesn't Matter What People Think
Lorelai and Max have their good moments along with reasons not to stay together, and it's true that when Lorelai dates Rory's English teacher, her life at school becomes tricky.
Paris tells everyone about this relationship, which is mean-spirited, and, while it's embarrassing for Rory, she also learns that it doesn't actually matter what other people think. She knows that her mom isn't trying to ruin her life or hurt her and that Max is a good person. She also knows that it doesn't reflect on her and that she's still a good person and student.
3 Get To Know People Before Judging Them
When Rory first encounters Tristan, he calls her "Mary," and it seems like he only wants to poke fun at her. It's not the best first impression for him to make.
Rory and fans alike think that Tristan is a mean kid who wants to start trouble, and yet, as time goes on, she realizes that he's hurt because of the end of his relationship. Rory learns that judging people before getting to know them isn't the best idea and she becomes more open-minded.
2 Everything Becomes Less Scary Over Time
When Rory and Lorelai are at Chilton for Rory's graduation, they think about how they were so scared of the school back on Rory's first day.
They say that it's not so scary now and they seem amazed by how much things have changed with the passage of time. Rory learns the important lesson that everything becomes less terrifying over time. At first, she's intimidated, but then she works hard, tries her best, and realizes that the other students are just as worried as she is about doing well and making a good impression.
1 Leave Your Comfort Zone Behind
Rory surprises fans in many ways, but it makes sense that she would want to attend Chilton. She believes it's her ticket to Harvard, and she wants to be in a tough academic environment.
Rory isn't comfortable at Chilton for a while, and it's tempting to want to go back to her hometown high school and forget all about these big dreams. But, Rory leaves her comfort zone and continues on her path, and she does achieve her goals, so it does seem worth it.
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