After Rory is accepted to the prestigious Chilton Preparatory School, Lorelai is forced to go to her wealthy parents for financial assistance. Her parents happily loan their daughter the money in exchange for an end to the estrangement and a family dinner every Friday night. Unfortunately, things hit a snag when a cute new transfer student flirts with Rory, leading the younger Gilmore to wonder whether leaving Stars Hollow High is really what she wants.
"Lorelai: Michel, the phone.This has got to be one of the best starter episodes ever - I loved the pacing & the witty banter.
Michel: Mm-hmm. It rings.
Lorelai: Can you answer it?
Michel: No. People are particularly stupid today. I can't talk to any more of them.
Lorelai: You know who's really nice to talk to? The people at the unemployment agency.
Michel: Independence Inn. Michel speaking."
Lorelai oversleeps on Rory's first day at Chilton, and discovers that all her good clothes are at the cleaners. She throws on a tiny tie-dyed top, Daisy Mae shorts, and cowboy boots to the dismay of Rory, the Chilton headmaster, and Emily, who has shown up for Rory's first day. Lorelai and Emily leave after some awkward moments in the headmaster's office, bickering the entire way out. Rory's day goes downhill from there. She's handed a three inch binder containing one week's worth of notes from one class and meets some insufferable classmates who are determined to make her life at Chilton miserable.
“Excuse me. There's a phone call for you, and if I am to fetch you like a dog, I'd like a cookie and a raise.” ~Michel
When Rory announces that she has to pick a team sport to play at Chilton, Emily insists that Richard take Rory to the club and teach her golf. Although Rory tees off to a rocky start, she soon gets into the swing of things and has a great time walking and talking with Richard. Meanwhile, Lorelai feels jealous of Rory's growing relationship with her grandparents, culminating in an explosive argument between mother and daughter.
"Is there a "You're Crazy" team? 'Cause I think they'd make you captain." ~Loralei
Max Medina gives Rory the first "D" of her life on an English paper. Lorelai spends the week helping Rory study for an important Shakespeare test but they sleep in on the big day. Sookie gets a rave review in a magazine, but fixates only on the critic's use of the word "fine" to describe her famous risotto.
"I guess this goes on the "boy, was I wrong" list, right above gauchos but just below the Flashdance phase." ~Lorelai
When both a distant family member and a neighbor's cat die, Lorelai has to decide which wake to attend. Max and Lorelai get their feelings for each other out on the table, but what will Rory think of this? Meanwhile, Lorelai and Sookie attend a Chilton bake sale, and Rory and Dean's budding relationship takes one step forward.
"You like coffee? Can we drink some together? A sort of pre-date. Very casual, no strings, no obligations. We'll just see if it's even worth going down the road of including food in the deal. Just coffee." ~Max
It's Rory's birthday, and her grandmother and mother each plan a party representative of their respective styles. Emily's elegant party so discomforts Rory that they argue. To make peace, Emily and Richard attend Lorelai's informal bash the next evening.
"Oh, I love pudding. I worship it. I have a bowl up on the mantel at home with the Virgin Mary, a glass of wine, and a dollar bill next to it." ~Lorelai
Dean gives Rory her first kiss; fearful of her mother's disapproval, Rory decides not to tell Lorelai for a little while; Lorelai gets stressed when she hears about the kiss from Mrs. Kim instead of Rory; Rory freaks out at first when Lorelai invites Dean over to watch videos and eat junk food, but ends up having a good time after all.
"Aw, come on. Are you mad at me too? I mean, a man can't choose whether or not he wants a picture of a fat, stupid bird on his wall? My God, that's the reason the damn Pilgrims came here in the first place. ~Luke"
It's snowing, and Lorelai is giddy. She runs into Max in Stars Hollow, and invites him back to her place. But they run into someone unexpected when they get there. Lane feels left-out of Rory's life.
"Rory, are you in any way malnourished or in need of some international relief organization to recruit a celebrity to raise money on your account?" ~Richardor
"Tradition is a trap. It allows people to stick their head in the sand. Everything in the past was so quaint, so charming. Times were simpler. Kids didn't have sex. Neighbors knew each other. It's a freaking fairy tale. Things sucked then too. It just sucked without indoor plumbing." ~Luke
After being pressured by her grandmother into "making the most of her high school experiences," super-shy Rory reluctantly decides to attend a Chilton formal--her very first dance--with Dean. Emily is on hand the night of the big event to see Rory off, but she ends up staying all evening to take care of Lorelai, who is suffering from back problems. All seems to be going beautifully as Rory and Dean discuss the next step for their relationship, and Emily and Lorelai enjoy some rare bonding time back at home, but a major blow-up is about to erupt when Dean and Rory make an unwise decision after leaving the dance.
"No! I just meant boyfriend in the sense that the whole defending me thing was very boyfriendy, but only in the broadest sense of the word, which doesn't even apply at all here." ~Rory
Things are still chilly between Rory and Lorelai; Lane gives Rory advice about the right Christmas gift for Dean; Emily and Lorelai have a tiff about Christmas dinner, leaving Rory to go by herself; Dean and Lorelai patch things up; Luke makes a lonely Lorelai a Santa burger; Richard collapses and is rushed to the hospital; Luke gives a car-less Lorelai a ride to the hospital; relieved that Richard's collapse was only a bout of angina, the Gilmores settle their differences.
"Richard Gilmore, there may be many things happening in this hospital tonight, but your dying is not one of them. I did not sign on to your dying, and it is not going to happen. Not tonight, not for a very long time. In fact, I demand to go first. Do I make myself clear?" ~Emily
As Lorelai and Max grow closer, Rory begins to get attached to the idea of Max in their lives, which worries Lorelai; Sookie and Lorelai have a frank discussion about relationships; Lorelai tries to ease out of her relationship with Max during Parent's Day at Chilton, but ends up passionately kissing him in his classroom just as Paris walks by; stung by the details in the newspapers about her parents' messy divorce, Paris tells everyone in the lunchroom about Max and Lorelai to deflect gossip away from her and towards Rory; Rory confronts Paris, gets an apology, and offers a sympathetic ear, which is grudgingly accepted; Sookie asks Jackson out on a date and he accepts.
"You want me to serve my customers a genetically engineered vegetable that's named after a butt?" ~Sookie
After Lorelai encourages Sookie to ask out Jackson, she finds herself on the double date from hell with Jackson's cousin, Rune, which makes Luke jealous enough to finally work up the courage to ask Lorelai out. Meanwhile, Rory and Lane get into trouble when they double date with Dean and his friend Todd without telling their moms.
"Judging from their clothing, a town where high rubber fishing boots and spittoons would be considered formal wear." ~Michel
Lorelai organizes the Stars Hollow Charity Rummage Sale, which leads her to learn some details about Luke's romantic past. Meanwhile, Lorelai, Sookie, Rory, Paris, Madeline and Louise attend a Bangles concert in New York, which leads to Lorelai busting Madeline and Louise at an older boy's party.
"Yeah, see those two idiots over there? They're 16...underage and I bet you're not. I also bet those big fancy party cups aren't holding lemonade. You really want to end any further conversations with me so step aside Skippy. Move your asses outside...now! Hey, I am not even going to begin to tell you how completely insane it is to take off with anyone you don't know, or drink things that you don't know what's in them, or act like you have a clue when you don't, but so help me God if you ever pull a stunt like this again, it will not be around my kid! Do you understand me?" ~Lorelai
An evening of "The Donna Reed Show" reruns infects Dean and both Gilmore Girls -- Dean expresses a longing for the type of family represented by the show, Lorelai helps Luke spruce up the diner with a fresh paint job and new curtains, and Rory dresses up like Donna and fixes a 1950s style dinner for Dean while petsitting Babette's new kitten; when the baby chick that's the subject of Rory's midterm project gets loose in the house, Lorelai frantically calls Luke to help her search the house; both Sookie and Emily force Lorelai to confront her feelings for Luke; Christopher roars into town on his motorcycle, and agrees to stay at Lorelai's and Rory's during his visit.
"To Luke's. We're picking out paint colors tonight, so it's gonna be hours of "yes, no, yes, no, yes, no," until my world-famous perseverance wears him down and he winds up in a ball on the floor crying like a girl. Wanna come watch?" ~Lorelai
Wanting to play a greater role in Rory's life, Christopher settles in for his visit and lets Rory give him the grand tour of Stars Hollow. When his parents arrive in Hartford for a visit, Emily invites everyone to Friday night dinner, which turns out to be an unqualified disaster after Richard nearly comes to blows with Christopher's father over critical comments about Lorelai. In the aftermath of the ruined dinner party, Richard retreats to his study to calm down, Emily makes a plate for Rory in the kitchen and reassures her how much she is loved and regarded, and Christopher finds Lorelai on the balcony of her old bedroom and comforts her by repeating a little romantic history. The next morning, Lorelai awakens with a start, horrified that she forgot to help Luke paint the diner after dinner on Friday night. Grabbing a jacket, she races to the diner still clad in her pajamas, and begs Luke's forgiveness. He shrugs it off at first, but appears somewhat wounded when he realizes that Lorelai was with Christopher the night before. When Lorelai returns to the house, Christopher asks her to marry him and she regretfully turns him down, claiming he's not ready for the responsibility of a family quite yet. Christopher returns to California with the promise of doing a better job of staying in touch. The next morning, Lorelai surprises Luke by having the diner completely repainted when he arrives to open up for the day.
"Behold the queen of the sudden transition!" ~Christopher
Luke's ex-girlfriend Rachel arrives in Stars Hollow unexpectedly, and immediately picks up on the attraction between Luke and Lorelai, which they deny. Rachel decides to stay for awhile, which leaves Luke and Lorelai with mixed feelings. Lorelai and Rory are amazed when Emily agrees to excuse Rory from Friday night dinner so that Rory and Dean can celebrate their three month anniversary. When Lorelai arrives for dinner, she discovers the source of Emily's largesse -- her mother has invited another guest -- a man with whom she secretly hopes to fix Lorelai up. Back in Stars Hollow, Dean treats Rory to a wonderfully romantic dinner, and then gives her a present: a car that he's restoring for her, but he has an even bigger surprise planned for her that leaves her unable to respond.
"It's a crazy festival based on a nutty myth about two lunatics who in all probability did not even exist and even if they did probably dropped dead of diphtheria before age 24. The town of Stars Hollow probably got its name from a local dance hall prostitute or two rich drunk guys who made up the story to make it look good on a poster." ~Luke
Rory decides to engage in a flurry of activity to avoid thinking about Dean, despite Lorelai's advice to wallow; Lorelai runs interference as the residents of Stars Hollow reach out to console Rory and Luke attempts to bar Dean from the diner; Rachel pitches in to help Luke out at the diner; Jackson prepares dinner for Sookie, and has a tough time keeping her out of the kitchen; Rory decides to attend Madeline's party and takes Lane along for company; Lorelai decides to visit Max when she realizes how much she misses him; Lane is torn when she meets the perfect guy at the party; Rory attempts to befriend Tristan after he has very public breakup with his girlfriend at the party, and when he apologizes for his past bad behavior towards her and kisses her, she bursts into tears; at home, Rory sobs to Lorelai that she's ready to wallow now.
"She's been here five minutes and already has a date. I've been going to this school for nine years and I'm the french soda monitor." ~Paris
Emily becomes unhinged at the prospect of a visit from Richard's mother Trix; Paris is outraged when she discovers that Tristan asked her for a date at Rory's urging; fearing that she'll never see Lorelai again, Emily opposes Trix's offer to set up a trust fund for Rory.
"Do you know that every night at dinner the Kennedy clan would sit around the table having lively debates about everything under the sun. They would quiz each other about current events, historical events and intellectual trivia. Now the Gilmore clan is just as smart and wordly as the Kennedy's so come on someone say something.
~Emily
Rachel finds an abandoned inn that Lorelai and Sookie fall in love with; Lorelai and Rachel spend the afternoon getting to know each other and Rachel asks Lorelai to put in a good word for her with Luke; as Rory takes Emily on a tour of Stars Hollow, Emily hits it off with Mrs. Kim and Michel, but becomes distraught when she sees Lorelai and Rory's first home; at Sookie's urging, Lorelai gives Jackson's cousin, Rune, a job at the Inn.
"Oh hey, Kirk. You gettin a cold? You know, you should try that Dyna-Meda-Chema-Themytol. Knocks it right out. But don't drive a forklift though, cause it'll make you drowsy." ~ Lorelai
Lorelai helps Luke shop for a birthday present for Rachel and goes wild outfitting him with a new wardrobe; overwhelmed by sadness at her breakup with Dean, Rory is distressed to discover that Lane and Dean have become science project partners, and incensed to find out from Max that Lorelai has neglected to mention that they are dating again, so she argues with Lorelai and then takes off for Hartford to spend the night at her grandparents' house without telling her mother; when an angry Lorelai confronts Dean and discovers the truth about his breakup with Rory, she fears that she has taught Rory not to commit to a relationship.
"I'm talking about my own personal lack of commitment skills. I mean, look, I love that you have my eyes and my coffee addiction and my taste in music and movies, but when it comes to love and relationships, I don't necessarily want you to be like me. I would hate to think that I raised a kid who couldn't say I love you." ~Lorelai
Paris wreaks her revenge after Tristan lies about going to a concert with Rory; Rachel leaves Stars Hollow after she becomes convinced that despite his protests, Luke is in love with Lorelai; Rory's defense of the Stars Hollow troubadour during a town meeting brings her back together with Dean, enabling her to finally say, and mean, the words that he's been longing to hear; Luke and Max meet and engage in a little not-so-friendly rivalry as Max begins to suspect, despite her protests, that Lorelai and Luke were once an item; Max proposes to Lorelai with a thousand yellow daisies.
"It should be magical. There should be music playing and romantic lighting and a subtle buildup to the popping of the big question. There should be a thousand yellow daisies and candles and a horse and I don't know what the horse is doing there unless you're riding it, which seems a little over the top, but it should be more than this." ~Lorelai
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