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- DirectorLesli Linka GlatterStarsLauren GrahamAlexis BledelMelissa McCarthyRory is accepted into the elite Chilton prep school. Bad news for Lorelai: she must make amends with her parents to borrow the money for Rory's tuition. The money is available--with strings attached.
- 2000–200744mTV-PG8.0 (1.5K)TV EpisodeDirectorArlene SanfordStarsLauren GrahamAlexis BledelMelissa McCarthyRory's first day at Chilton, where she has a confrontation with Paris. Emily tries to install an internet connection at Lorelai's house without asking first.
- DirectorAdam NimoyStarsLauren GrahamAlexis BledelMelissa McCarthyRory goes golfing with her grandfather and surprisingly has a good time. At Lorelai's inn, a wedding is stressing everyone out.
- DirectorAlan MyersonStarsLauren GrahamAlexis BledelMelissa McCarthyRory receives a bad grade as she still struggles to catch up at Chilton.
- DirectorMichael KatlemanStarsLauren GrahamAlexis BledelMelissa McCarthyLorelai is struck by two deaths; Lorelai decides to finally confront Max with her feelings for him, and he tackles his feelings as well.
- DirectorSarah Pia AndersonStarsLauren GrahamAlexis BledelMelissa McCarthyIt's Rory's birthday. She gets two parties. An elegant and horrible affair thrown by her grandmother and an informal fun party thrown by Lorelai.
- DirectorRodman FlenderStarsLauren GrahamAlexis BledelMelissa McCarthyRory gets her first kiss from Dean. The whole town is buzzing about it, yet Rory has not told Lorelai.
- DirectorAlan MyersonStarsLauren GrahamAlexis BledelMelissa McCarthyIt'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.
- DirectorLesli Linka GlatterStarsLauren GrahamAlexis BledelMelissa McCarthyRory and Dean attend a formal dance at Chilton. A mishap leads to a fight between Emily and Lorelai.
- DirectorBethany RooneyStarsLauren GrahamAlexis BledelMelissa McCarthyRichard Gilmore is rushed to hospital after collapsing at the Christmas party. Luke goes with Lorelai to the hospital, where Emily and Rory already are.
- DirectorDavid PetrarcaStarsLauren GrahamAlexis BledelMelissa McCarthyAs the relationship with Rory's teacher Max grows more serious, Lorelai panics and decides to end it, but her attempt to break up with him during Parent-Teacher night at Chilton causes even more trouble at school for Rory.
- DirectorLev L. SpiroStarsLauren GrahamAlexis BledelMelissa McCarthyTwo double dates. Rory and Dean set up Lane with Dean's friend and the four go out. Meanwhile Sookie and Jackson's first date includes Lorelai and Jackson's cousin, who's very very weird. Lorelai does not enjoy the evening.
- DirectorBruce Seth GreenStarsLauren GrahamAlexis BledelMelissa McCarthyLorelai gives Rory, Paris, Madeline and Louise tickets to a Bangles concert, but the evening doesn't go quite as planned.
- DirectorMichael KatlemanStarsLauren GrahamAlexis BledelMelissa McCarthyRory and Dean fight, because Dean likes the idea of a 50s type house wife. Rory ends up pretending to be such that type of woman for an evening.
- DirectorMichael KatlemanStarsLauren GrahamAlexis BledelMelissa McCarthyChristopher visits Stars Hollow to see Lorelai and Rory. They all come to dinner at Rory's grandparents' house.
- DirectorEriq La SalleStarsGinnifer GoodwinJennifer MorrisonLana ParrillaIn flashbacks, Ruby and Mulan find themselves in Oz, where they meet Dorothy. After the three witness Zelena's return to Oz, they look for a way to defeat her once and for all. However, Dorothy mysteriously disappears.
- 2000–200745mTV-PG8.1 (1K)TV EpisodeDirectorLesli Linka GlatterStarsLauren GrahamAlexis BledelMelissa McCarthyIt's Rory and Dean's 3-months anniversary, and he plans a special surprise, but it doesn't quite go as he planned. Luke's old girlfriend, Rachel, turns up.
- DirectorNick MarckStarsLauren GrahamAlexis BledelMelissa McCarthyRebounding from a fight with Dean, Rory ends up kissing Tristin at a party, while Lorelai follows her own impulse to show up at Max's house for a night of passion.
- DirectorMichael KatlemanStarsLauren GrahamAlexis BledelMelissa McCarthyLorelai's paternal grandmother arrives from England and stresses Emily out in a big way.
- DirectorPerry LangStarsLauren GrahamAlexis BledelMelissa McCarthyRory takes her grandmother around Stars Hollow for a day. She's horrified to see where Lorelai and Rory first lived.
- DirectorLev L. SpiroStarsLauren GrahamAlexis BledelMelissa McCarthyLorelai and Max start dating again. After a fight with Lorelai, Rory spends the night at her grandparents' house. Lorelai confronts Dean about the break-up.
- DirectorAmy Sherman-PalladinoStarsLauren GrahamAlexis BledelMelissa McCarthyLorelai and Max's relationship gets more serious. Luke's girlfriend Rachel returns. Meanwhile, Rory tries to win Dean back.
- DirectorAmy Sherman-PalladinoStarsLauren GrahamAlexis BledelMelissa McCarthyLorelai accepts Max's proposal. Rory takes Dean to dinner at her grandparents' house.
- DirectorMichael KatlemanStarsLauren GrahamAlexis BledelMelissa McCarthyLorelai hesitates to tell her parents about her engagement to Max, despite Rory's urging. Rory and Dean have a spat over Rory's plans for extracurricular activities.
- DirectorGail MancusoStarsLauren GrahamAlexis BledelMelissa McCarthyDuring a prenuptial party thrown by Sookie, Lorelai has misgivings about her engagement.