The first day of school is always awkward and nerve-wracking. People worry about getting lost on the way to English class or not having anyone to eat lunch with. When Rory started attending Chilton on Gilmore Girls, she had piles of homework, new classmates, and a competitive Paris to worry about.
Rory was always a big reader and kept books in her purse at all times. The second episode of the series, "The Lorelais' First Day At Chilton," proved that starting a new journey wasn't easy for a teenage girl or for her mother. There are many scenes that make fans laugh, blush, and sympathize with all these years later.
Lorelai Painted Rory's Toes Red The Night Before The First Day
In the opening scene of "The Lorelais' First Day At Chilton," Lorelai and Rory sat on their front porch while Lorelai painted her daughter's toenails red. Rory kept eating whipped cream right out of the can, which was funny and introduced fans to the mother and daughter's junk food-eating habits.
Rory said she didn't know why she needed red toenails when she would be wearing shoes and Lorelai joked, "Okay, but everybody knows that private school girls are bad, and bad girls always wear red nail polish." It was only the second episode of the series and already, viewers knew that Lorelai had a witty answer for everything.
Rory Woke Lorelai Up In A Total Panic
Rory made many mistakes over the years, but she always tried to be a model student. She prided herself on being on time and always getting her work done.
In this episode, Rory's first day at Chilton was already off to a rough start when she realized that she overslept. She said to Lorelai, "I can't be late on my first day of school. Do you know what happens to people when they're late on their first day?" which perfectly sums up Rory's studious and careful nature. This was a memorable moment as Lorelai scrambled to find something to wear, which Gilmore Girls fans know was a super humiliating outfit.
Lorelai Revealed Her Awkward Outfit In Headmaster Charleston's Office
Gilmore Girls fans know that when Lorelai didn't pick up her suit from the dry cleaners, she wore an inappropriate outfit of a pink tie-dye t-shirt and jean shorts. She put on a long brown coat and hoped that no one would notice. Of course, Rory wanted Lorelai to meet Headmaster Charleston with her, and Lorelai was told that if she kept her coat on, it would be considered rude.
This was even more embarrassing since Emily was there, too, as Headmaster Charleston was part of her social circle and she wanted to be involved. Of course, Lorelai was offended and took this to mean that Emily was going to control the experience, but Emily meant well.
Charleston Told Rory That Chilton Would Be Super Tough
Headmaster Charleston was always very intimidating, which is why it was so satisfying when he asked Rory back in the Netflix revival A Year in the Life.
In this episode, he told Rory that she shouldn't be so quick to think she would succeed at her new school. He said, "Chilton has one of the highest academic standards of any school in America. You may have been the smartest girl at Stars Hollow, but this is a different place." This was a big moment as it made Rory nervous that she didn't have what it took to make it.
Paris, Madeline, And Louise Stole Rory's File
Paris had a bad day, too, but for a different reason: she was annoyed that there was a new girl at school.
Paris said "We don't need any new kids here," and she and her friends Madeline and Louise stole Rory's file so they could get the scoop on her. This set up the complicated and tense relationship that Paris and Rory would have throughout the first season. Fans know that they eventually became friends, but back then, it didn't seem like Paris would ever be nice to her.
Lorelai Begged Luke For Coffee And Complained About Her Day
So many good episodes are about Lorelai and Luke and the characters had a sweet moment in this episode, too.
Lorelai went over to Luke's diner for some caffeine and compassion, telling him that she was having a horrible day. He asked, "That's how you dress to take Rory to Chilton?" and before she could explain, he said, "I mean, that's a fancy school." This made Lorelai feel even worse. Fans will always remember this scene as it was proof that when something went wrong in Lorelai's world, she went to Luke.
Paris Told Rory She Was Always Going To Win
Paris had a knack for honest statements and in the second episode of the series, she told Rory that she would always beat her at school. Most people would never tell someone that they were better than them, but Paris had no problem. She went over to Rory and said, "You'll never catch up. You'll never beat me. This school is my domain and the Franklin is my domain. And don't you ever forget that."
This was definitely a classic moment in the episode, as it foreshadowed the conflict that these two characters would have. Paris saw Rory as a huge threat, but Rory was just trying to get through her first day in a scary new place.
Tristin Called Rory "Mary"
While Tristin would eventually fall for Rory, in this episode he was curious about the new girl and called her "Mary." He said it enough times that she became very frustrated.
Rory had no idea what he was talking about and even yelled at him to stop calling her that name. When Lorelai picked her up at the end of the day, Lorelai said that he was referring to the Virgin Mary and that she couldn't believe teens were still using that old-fashioned insult.
Rory And Lorelai Hugged At The End Of The Day
While Lorelai did make parenting mistakes, she was always there for Rory when it counted, and she wouldn't miss the chance to hear how Rory's first day at Chilton went.
Rory ran over to her mom and hugged her immediately, and the hug lasted for a long time. It was an incredibly sweet moment that drove home the close relationship that Rory and Lorelai have. Sometimes someone just needs their mom and that was exactly how Rory felt.
Lorelai Asked Rory If She Thought Luke Was Cute
Rory and Lorelai spent many episodes at Luke's diner and it was only natural that they would stop by at the end of this episode.
Fans will remember that Lorelai asked Rory if she thought that Luke was attractive. Rory said, "You cannot date Luke," and Lorelai replied, "I said nothing about dating Luke." Rory said, "If you date him, you'll break up, and we'll never be able to eat there again." This was hilarious and set up the flirty banter and "will they or won't they?" interactions between Lorelai and Luke. In the next shot, Luke was watching them, and fans couldn't wait to watch the next episode.