Rory's high school years at Chilton make up some of the most compelling episodes of Gilmore Girls. From studying harder than she ever anticipated to wondering if Paris will ever like her, Rory has a rocky beginning and her academic years only become more intense as time goes on. While Rory gets used to this tough school, fans learn more about her classmates, teachers, and potential friends, becoming just as invested in their lives as Rory and Lorelai's.
From a classmate who crushes on Rory to a few students with competitive personalities, there are many side characters at Chilton on Gilmore Girls who have impacted the story in fascinating ways.
Mrs. O'Malley
Fans meet Mrs. O'Malley when she's in charge of an event where Chilton students are debating other students, and she also works as The Franklin's faculty advisor.
Since Mrs. O'Malley doesn't get as much screen time as Rory's English teacher (and Lorelai's fiance) Max, she isn't quite as interesting as some other people at Chilton. But she does pop up sometimes and proves that this school is a formal, demanding place, which is important.
Ian Jack
Lorelai talks to Ian when she's bringing Rory to Chilton during the Gilmore Girls episode "The Lorelais' First Day At Chilton." While he wants to go out with Lorelai, she thinks that dating a Chilton parent would be stressful and embarrassing for Rory.
Of course, fans know that things do get tough for Rory when Lorelai dates and falls in love with Rory's teacher. But at this moment in the show, Ian helps viewers see that Lorelai takes her dating life seriously and tries to make sure that Rory is comfortable.
Headmaster Charleston
Headmaster Hanlin Charleston doesn't mince any words or make life easy for Rory when she first meets him. He makes a point of telling her that while she was a star at her old school, that's not the case here, as she might fail. Charleston also shows up in a few scenes, whether Lorelai is yelling at him or he's talking about his respect for Emily.
Headmaster Charleston doesn't seem like a very good or compassionate person, so he isn't as likable as some of the other minor characters at the school. He does play a key role in making Rory want to prove herself, though.
Madeline Lynn
Of all of Rory's most memorable Chilton moments, learning how different she is from her new Chilton classmates is definitely up there. Rory has trouble figuring out how to bond with Madeline, who cares about dating and not much else.
Rory spends some time with Madeline, Louise, and Paris when they all attend The Bangles concert in season 1, and after that, it's clear that Rory will be polite to Madeline but doesn't think that they will be great friends. Madeline's ditzy personality adds a bit of humor but she's not as well-crafted as some other characters.
Brad Langford
Fans love watching Brad realize that he doesn't need to be so fearful of Paris and that she can't really hurt him after all. Brad has some great character development when he leaves to star in Broadway and comes back a more confident person.
Out of all the Chilton side characters, Brad has a true arc that is fun to see, and he helps viewers realize that Paris wants to be intimidating, but it's totally possible for people to feel powerful and stand up to her. This is something that Rory does as well.
Max Medina
While Lorelai doesn't want to date a parent at Chilton, she falls for Max hard. Some viewers think that Lorelai should never go out with Max and others think that she does try to figure the situation out and make it better for Rory.
Max treats Lorelai and Rory in a caring way, trying to help Rory adjust to the high workload and talking to Lorelai about how their relationship can work. While they do break up, Max is a memorable Chilton character who would be missed, as Lorelai realizes that while things aren't right with Max, she's meant to be with Luke.
Henry Cho
Lane's Gilmore Girls boyfriends Dave and Zack are sweet and beloved characters, and Henry is another love interest of Lane's who makes a good impression on viewers.
Since Lane likes Chilton student Henry, she and Rory go to a party and Lane hopes that she and Henry can have a secret relationship. Unfortunately, they split up when it becomes too difficult, but Henry is always compassionate and polite. He shows Lane that love is out there for her and that is a big deal.
Tristan Dugray
From kissing Rory at a party after Dean breaks up with her to teasing her most days of the week, Tristan plays a crucial part in Rory's life at Chilton. He also unknowingly creates drama between Rory and Paris when he and Paris go on a date and it goes badly.
While Tristan seems a bit mean at first, Rory sees a soft side of him that she likes, although she still loves Dean and doesn't want to date Tristan. Fans realize that he's a lonely person having a tough time as his family ignores him and he and his girlfriend Summer break up. Tristan adds some excitement to Chilton, making him an important side character.
Louise Grant
Gilmore Girls fans who love Paris and Rory's relationship also enjoy seeing Paris interact with Louise and Madeline, who she just doesn't understand.
Louise is a solid character who seems intelligent, but she doesn't want to put in the work the way that Paris and Rory do. Louise's scenes are fun to watch as she always has an air of mystery around her and fans wonder what she's thinking.
Francie Jarvis
Francie is definitely the most entertaining minor character at Chilton on Gilmore Girls, thanks to her competitive and confident personality.
Francie runs The Puffs, the secret society who tries to recruit Paris and Rory, although Charleston finds out about it and that's the end of that. While Rory and Francie don't become friends, Paris and Rory do become united in their dislike of her, and that makes Francie the impetus for a lot of drama that fans have enjoyed seeing.