By season six of Gilmore Girls, Rory had stolen a boat and dropped out of Yale, and her relationship with Logan was still super dramatic and tense. Lorelai was engaged to Luke but that wasn't perfect, either. Rory and Lorelai are equally popular since they're the two main characters of Gilmore Girls, and no one would have expected them to have such a bad fight that they would put a pause in their close mother/daughter bond. But that's exactly what happened in the sixth season.
While the sixth season had some scenes that had fans laughing, other moments were painful to watch, as the characters went through many personal struggles that set them up for the final season.
Funniest: Lorelai Got Her Dog, Paul Anka
In season six, Lorelai got a dog she named Paul Anka and the two were the best of friends.
Like Lorelai, Paul Anka was super quirky and charming, and he became a big part of Lorelai's universe. This was a light moment in a season that would otherwise feel pretty heavy and serious since the majority of the episodes were about the changing relationship between Lorelai and Rory. While they would thankfully reconcile, they did spend a period of time not talking to each other, which was total torture for Gilmore Girls fans. It was great that Lorelai had Paul Anka to lean on during this tough time.
Saddest: Lorelai Realized Rory Was Slipping Away From Her
In the season six premiere "New and Improved Lorelai," Lorelai was done trying to convince Rory to stay at Yale and remain on her regular path. She resigned herself to the fact that Rory was going to live with her grandparents and that there was nothing she could say or do.
This was tragic to watch, as Lorelai had always been someone who Rory listened to, no matter what. Now, it was clear that Rory was starting to slip away from her, and that Lorelai was spiraling.
Funniest: Lorelai Hated The Proposed New Street Name For The Dragonfly Inn
In the season six episode "Welcome to the Doll House," Taylor wanted to rename all of the streets of Stars Hollow and he was inspired by what they were called back in the day.
This was one of the funniest moments of the sixth season, as Lorelai couldn't believe what her street name was: Sores and Boils Alley. This was classic Taylor, as he often had grand ideas that he would bring up at the town meetings, and he would become increasingly flustered that no one else seemed to see things from his unique perspective.
Saddest: Lorelai Called Rory, Who Got A New Number And Didn't Give It To Her
While Rory had a similar personality to Lorelai, she sometimes made decisions that were cold and harsh, and it's hard to see her mom acting that way.
Lorelai got an unhappy surprise in the episode "Always a Godmother, Never a God" when she called Rory and it turned out that the cell phone number wasn't in service anymore. Rory had gotten a new phone without giving it to her. Lorelai felt terrible and it was another reminder that she was losing her daughter.
Funniest: Luke Hated Spending The Weekend With Logan
The episode "A Vineyard Valentine" brought some much-needed humor to this season.
Logan, Rory, Luke, and Lorelai all spent the weekend at Logan's family's Martha's Vineyard home, and Luke had a lot of trouble getting along with Logan. Seeing these two characters together was priceless as they would never have hung out otherwise. It was clear that Luke, who lived in backward baseball caps and liked his small-town life, would have nothing to talk to rich kid Logan about. Luke told Lorelai that he wasn't sure he should like Logan, and he also worried about the weekend in general: he said, "It's weird staying at people's houses, tiptoeing around, using their sheets, drinking their weird tap water."
Saddest: Jess Was Upset About The Way Rory's Life Turned Out
Jess had a sad history but when he and Rory reconnected in the sixth season episode "Let Me Hear Your Balalaikas Ringing Out," it was Rory who seemed tragic.
Jess was upset that Rory's life had turned out to be so messy. He didn't like that she left Yale and that she was living with Emily and Richard. He told her that he was working in publishing and had even written a book that got published. It was amazing for her to see how well he was doing but a sad reminder of what she was doing (which, of course, was not much).
Funniest: Paris Lashed Out At The Yale Daily News Staff
While it seemed like fate that Paris would be the editor of the Yale Daily News, it didn't last forever, and her fellow young journalists weren't pleased with her.
The sixth season episode "You've Been Gilmored" saw Rory replacing Paris in the editor job. While this caused big problems in their friendship, it was pretty hilarious watching Paris reign over the rest of the staff members, as she got too obsessed with her perceived power. Paris didn't always have funny moments so this was a good one.
Saddest: Rory Found Out Logan Slept With Others During Their Break
Rory was heartbroken in the episode "Bridesmaids Revisited" as she found out that Logan had slept with some other women during the break that they took from each other.
While Logan seemed to think that was perfectly justified, Rory thought they were taking time apart so they could figure out how to be in a happy and healthy place together. She was so upset and it was really sad watching her deal with this tough news.
Funniest: Rory Cried Over Coffee, Then Logan Bought Her A Coffee Cart
Rory and her mom loved coffee, no doubt about it. In "The Perfect Dress," Rory went to therapy and talked about how awkward it was going to be bumping into Logan all over Yale since they were having problems. She realized that she always saw him at her favorite coffee cart and said, "I don't know what I'm gonna do, I don't think I can take running into him every day in the halls, and in the paper and the coffee cart... Oh my god! I'm gonna have to quit drinking coffee! And I love coffee!"
In the episode "Just Like Gwen and Gavin," Logan bought Rory a coffee cart and hired a guy named Ben to literally follow her around with it. This was really funny to watch since, of course, Rory loves coffee so much that he knew this would be the way to her heart. Rory found it pretty annoying.
Saddest: It Seemed Like Luke And Lorelai Were Going To Break Up
Luke made some bad decisions and that included keeping his daughter April a secret from Lorelai. This caused major issues in their relationship and it was hard not to side with Lorelai, as she had already invested so much of herself in Luke.
The season six finale "Partings" found Luke and Lorelai in a horrible place. It was implied that they were going to break up, and sure enough, they weren't together in the seventh and final season. This was one of the saddest moments of the sixth season, as they were both completely heartbroken, but it seemed like they couldn't get past the April problem.