- Rory – Jerk, ass, arrogant, inconsiderate, mindless, fratboy, lowlife, butt-faced miscreant!
- Logan – (mock-offended) Butt-faced miscreant?!
- ―Yale flirting 101
LOVE AND WAR – Rory (Alexis Bledel) is delighted when the headmaster (guest star Dakin Matthews) of her old prep school asks her to play hostess to a young student, Anna (guest star Sara Foret), who is thinking of applying to Yale.
However, Anna turns out to be more interested in boys than academics and runs off to party, leaving Rory to deal with Logan's (Matt Czuchry) elaborate practical jokes. Meanwhile, Lorelai (Lauren Graham) and Luke (Scott Patterson) have their first fight when she accidentally upsets him by buying an old boat that had belonged to his father.
- Miss Patty celebrates her 40th anniversary of working in showbizz. She did her first play in Cleveland in 1964.
- Paris and Doyle hook up and are mostly a couple for the remainder of the series.
- Paris's life-coach Terrance returns, after court-mandated rehab.
- Luke has a dark day every year in November on the anniversary of his father's death, where he vanishes and spends time alone.
- Marty gets annoyed with Rory's obliviousness to Logan liking her and expresses it for the first time, puzzling Rory.
- Richard – Oh, you're going to show her the Guttenberg?
- Lorelai – Steve?
- Richard – (bemused) Bible
- Lorelai – Right.
- Lorelai – You're, like, hotter than Willy Wonka
- Luke – I am not hotter than Willy Wonka
- Lorelai – Business? Now you're Willy Loman?
- Lorelai – Because you keep those crazy, anal, Bob Graham kind of notebooks.
- Rory – Yes, he is. But not as cute as Pushkin. Right this way, missy.
- Rory – It's 11 o'clock at night. Who do you hope to hook up with, Spike and Drusilla?
- Sookie – I mean, who has three Thigh Masters besides Suzanne Somers?
- Lorelai – Great! Then I'll hop a fence and get Richard Widmark to sign my grapefruit.
- Paris – Seriously, you've got a minute to make an impression and that's all you can come up with? You want to know my sign too, Jack? Or how about my favorite color? Or if I'm a Britney or a Christina?
- Paris – So you've been reading about those skeletons they've been finding on the island of Flores, right?
- Doyle – Oh, yeah. And they're only 13,000 years old. That's nothing in geological time.