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1. "Nick & Nora/Sid & Nancy" - Season 2 Episode 5
The one where Jess arrives to Stars Hallow. We get one of my favorite Luke scenes. Two words: "Jam Hands."
2. "The Bracebridge Dinner" - Season 2 Episode 10
The one where Lorelai and Sookie throw a Renaissance-themed dinner for the town at the inn. This one is particularly great because Jess and Rory emotionally connect on a sleigh ride and Richard and Emily interact with members of the town.
3. "There's the Rub" Season 2 Episode 16
The one where Lorelai and Emily go to a spa, and Rory, Jess and Paris eat takeout and talk books. Yes, Rory and Dean have a spat, as do Lorelai and Emily. But they are lighthearted spats that resolve quickly. Also, Jess has read Jane Austen... swoon.
4. "The Fundamental Things Apply" - Season 4 Episode 5
The one where Rory goes on a date with water bottle boy, and Luke and Lorelai have a movie night. How much I relate to Lorelai's movie night rules is startling. This episode may give you "a nice musk."
5. "Dead Uncles and Vegetables" - Season 2 Episode 17
The one where Luke's uncle Louis dies. Rory and Lorelai help him at the diner. I love this episode because we get to see Lorelai help Luke. He's always helping her, and finally the tables are turned.
6. "Written in the Stars" - Season 5 Episode 3
The one where Paris throws a wake attended by Emily. Rory meets Logan for the first time. This one is for all you Logan lovers out there. We get one of my favorite Paris Geller lines: "No Rory, this great man was not brought down by my vagina."
7. "Take the Deviled Eggs" - Season 3 Episode 6
The one where Lorelai and Rory go to Sherry's baby shower. This episode is worth enduring the cheesy baby shower dialogue (e.g. "What are we waiting for? Let the games begin!") entirely for the last five minutes. The town gathers to watch a protest.
The one where Rory has a Chilton student stay with her at Yale. The best part of this episode is Paris attending a speed dating session.
9. "Those Are Strings, Pinocchio" - Season 3 Episode 22
The one where Rory graduates from Chilton. I usually don't like to re-watch season finales because Amy Sherman-Palladino is the queen of cliff hangers. Actually, that's probably Shonda Rhimes. But it usually leads me to start watching the next season, and some times, you just don't have time for that. But this one beautifully closes a chapter of both Rory and Lorelai's life.
10. "A Deep-Fried Korean Thanksgiving" - Season 3 Episode 9
The one where Lorelai and Rory go to four Thanksgiving dinners. Lane and Dave have a great time. Lorelai, Luke, Jess and Rory have a Thanksgiving dinner together. All is right with the world. Also, probably a top three Sookie scene. Melissa McCarthy showing off her Groundlings background.
Honorable Mentions, Because I Can't Decide"A-Tisket, A-Tasket" - Season 2 Episode 13 - The one where Luke and Lorelai go on a "date," as do Jess and Rory. All is right with the world.
"You've Been Gilmored" - Season 6 Episode 14 - The one where Luke and Lorelai have dinner with Richard and Emily. We see Richard and Emily finally accept Luke as a match for Lorelai. Rory gives Christopher a tour of Yale and Paris accuses Rory of putsch-ing.
"Friday Night's Alright for Fighting" - Season 6 Episode 13 - The one where all the Gilmores fight at a Friday night dinner. Seemingly an odd choice, but seeing each one air grievances against the others is cathartic as an audience member. And its shot to perfection; well done Kenny Ortega. Also, we get to see Logan be charming for a reason other than his wealth.
"Christopher Returns" - Season 1 Episode 15 - The one where we meet Christopher for the first time. His past with Lorelai is so believable: acting at its finest.
"Lorelai? Lorelai?" - Season 7 Episode 20 - The one where the town sings Karaoke. We see that Rory isn't perfect. I watch this one when I feel bad and I need Lorelai to cheer me up. It does have a cliff hanger though...