Gilmore Girls: 10 Worst Mistakes Rory Made At Chilton

When Rory learns that she's been accepted to Chilton, the Gilmore Girls character couldn't possibly be more excited. She loves that she's going to get an incredible education and have a better shot at a Harvard acceptance letter. When Rory begins attending classes, she realizes that between the incredibly heavy workload and her mean new classmates, this might not be the smoothest place to finish her high school years.

RELATED: 10 Reasons Why Rory Was Best At Chilton On Gilmore Girls

While Rory gets good grades and excels at Chilton, becoming valedictorian and even inspiring students in the Netflix revival, she makes many mistakes during her high school years that could definitely be avoided.

10 Rory Should Stand Up To Paris As Soon As Paris Spreads The Lorelai/Max Gossip

Rory and Paris are sometimes enemies, especially when Paris tells their classmates that Lorelai and Max are in a relationship. Rory is really upset that Paris is gossiping about her.

Rory hopes that the rumor will go away, and she tries to ignore it, but not talking to Paris about what she's done is definitely a big mistake. As soon as Rory and Paris begin actually talking to each other, Rory realizes that Paris is nicer than she seems, so it's likely that this conversation would go well.

9 Rory Could Tell Tristan Not To Call Her Mary

While Rory is shocked and confused that Tristan calls her Mary, believing that he simply got her name wrong or is refusing to learn her real one, Lorelai lets her know that this means "Virgin Mary."

Rory does yell at Tristan and tell him her real name in the season 1 episode "The Deer Hunters," but Rory could also talk to Tristan earlier and let him know that he's bothering her. Since Tristan is a lot kinder than he appears to be at first, he would likely take this pretty well and would respect Rory for standing up to him.

8 Rory Doesn't Get Involved Until She's Forced To

When The Puffs recruit Rory or when she helps build a house in season 2, it's because Headmaster Charleston lets Rory know that she needs to play a larger role in the school's life.

RELATED: 10 Things That Make No Sense About Chilton On Gilmore Girls

It's hard to imagine Rory signing up for a club on her own, as she's shy and quiet and unsure about her new school, but this is definitely a mistake. She might feel more comfortable at Chilton if she got involved earlier on and it would help show Paris that Rory is trying to get through high school in one piece, just like her.

7 Rory Is Wrong To Scream During The Big English Exam

While Rory is a good student in many cases, she misses part of her English exam and receives an incomplete. Instead of owning up to the fact that she overslept, which was an honest mistake that anyone could make, she screams at Paris and Tristan as she's frustrated that they've been giving her such a hard time. Rory also messes up by not being very polite to Max, who is only trying to enforce the school rules.

While viewers understand how Rory feels here, she still makes a huge mistake and should go out into the hallway immediately so she can take a breath, calm down, and figure out what to do next. Rory has never been in trouble at school before, so it makes sense that she has no idea how to act.

6 Rory Shouldn't Want Dean To Watch Her Rehearsal

In the season 2 episode "Run Away, Little Boy," Rory and Tristan are rehearsing a Shakespeare play for school, and they end up in Stars Hollow since they have nowhere else to prepare. Tristan and Dean have a super dramatic fight when Dean watches the rehearsal.

While Rory likes to stay optimistic and often sees the best in people, she should tell Dean beforehand that he shouldn't watch, as it'll just cause tension and problems. Rory knows that Tristan likes her since they kissed at a party, and she can tell that things won't go well here.

5 Rory Jokes Around When She Meets Headmaster Charleston

It's definitely scary when Rory sits down with Headmaster Charleston at the beginning of season 1. He doesn't seem very kind or supportive as he shares that he's friends with her grandparents but that won't change the fact that many Chilton students are capable of failing.

Rory feels how awkward this conversation is, but instead of saying that she's going to work hard or is up to the challenge, she jokes, "So, you liked the lobster puffs, huh?" Charleston doesn't think it's funny that Rory makes a reference to one of Emily and Richard's parties, and it seems like Rory should be responding to what he's saying instead of trying to be funny.

4 Rory Could Ask Questions At The Chilton College Seminar

In the season 3 episode "Application Anxiety," Rory, Lorelai, and Emily are all upset about Rory's prospects for getting into Ivy League schools. While Rory choosing between Yale and Harvard works out, since she does get a great education at Yale, she doesn't feel confident about her academic future.

Rory goes to a college seminar at Chilton and when she hears a college rep say that they read too many applications about how inspiring Hillary Clinton is, she gets scared and anxious. But why doesn't Rory ask questions when the session is done? It seems like she could walk up to the rep and ask about how to put her best foot forward with her application.

3 Rory Misses School To See Jess In New York City

When Rory visits Jess in New York City, the focus is on the fact that she misses Lorelai's business school graduation, which is definitely a problem. But Rory also misses school, which is surprising and seems out of character for someone who cares so deeply about academics and her future.

RELATED: 10 Problems Gilmore Girls Fans Have With Rory And Jess, According To Reddit

While it makes sense that Rory wants to see Jess again since she's in love with him, it's a big mistake to skip school, especially since Chilton is such an intimidating and intense place.

2 Rory Wants Lorelai To Come Inside Chilton, Despite Her Outfit

The Gilmore Girls episode "The Lorelais' First Day At Chilton" is one of the most famous thanks to Lorelai's strange outfit. She hates that she's wearing boots, a tie dye t-shirt, and jean shorts to meet Headmaster Charleston, but Rory wants her to come inside since it's a special, important day.

Since Rory knows that her mom is wearing a totally inappropriate outfit, it doesn't make much sense that she wants Lorelai to come inside. Rory could go inside on her own and explain that Lorelai had to get to work, which would be understandable since at this point in the show, Lorelai runs the Independence Inn.

1 Rory Turns Down The Possibility Of Teaching At Chilton

In the Netflix revival A Year In The Life, Rory and Paris each give the students an inspirational talk, although of course Paris only manages to scare everyone. But when Headmaster Charleston tells Rory that he'd be happy to have her on the teaching staff, Rory hates the idea.

Rory has never seen herself as a teacher and is still interested in making her freelance journalism career happen. But it's too bad that she shoots Charleston down and doesn't take this more seriously, as Rory could definitely be a motivating teacher, even if she just did this for a year or two while trying to write on the side.

NEXT: 5 Reasons We’d Love To Go To Chilton On Gilmore Girls (& 5 We Wouldn’t)



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