The second season of Gilmore Girls debuted in October of 2001 and kicked off with drama galore. Lorelai is an engaged woman, Lane is set to go off to Korea because of her overprotective mother, and Luke's nephew Jess comes to stay with him and stirs the pot with Rory and Dean. With 22 episodes in the season, there was a lot that could go wrong.
And a lot did. But there were plenty of endearing and funny moments that happened as well. Lorelai became focused on her dream of owning an inn with Sookie, and Rory was no longer the new girl in school at Chilton. All seemed right in the world — until it inevitably came crashing down on them.
10 Funniest: Emily Was Invited To Lorelai's Bachelorette Party
At the end of season 1, Max proposed to Lorelai and she eventually accepted. Season 2 found Lorelai and Sookie talking about wedding plans, and the latter let the cat out of the bag to Lorelai's mother.
Sadly, Lorelai never got around to telling her mother about the engagement and it started a rift between the two women. Emily was still brave enough to attend Lorelai's bachelorette party, though. Seeing Emily Gilmore in a drag bar sitting with these stunning drag queens was iconic. She finally let her hair down and had fun with her daughter and friends.
9 Saddest: Lorelai & Sookie Were Denied Their Inn
In "The Ins and Outs of Inns," Lorelai and Sookie finally had the courage to talk to Fran about buying the old inn from her. Fran encouraged the ladies on their dream of owning an inn but refused to sell the property to them.
Fran told the women that the land had been in her family for generations and she wouldn't sell it to anyone until she passed away. It was devastating seeing Lorelai and Sookie's high come crashing down.
8 Funniest: The Booster Club Fashion Show
"Like Mother, Like Daughter" was a fun episode for the Gilmore women. Not only were Lorelai and Rory forced to step outside their comfort zone but Lorelai dragged Emily into the mix too.
Lorelai and Rory were scolded for not doing enough for their community. Rory didn't go the extra mile to make new friends and Lorelai wasn't doing enough to help out the school. To please Headmaster Charleston, Rory joined a new friend group ("the Puffs") and Lorelai helped the Booster Club host a fundraising event. At the event, Lorelai and Emily had to model clothes together, and as much as they were dreading it, both women had a blast.
7 Saddest: Lorelai Called Off Her Wedding To Max
As fun of a night as Lorelai's bachelorette party was, it all came crashing down when Lorelai realized she wasn't ready to marry Max. At the bachelorette party, Emily told the table how excited she was before she married Richard. She felt in control and safe. It was at that moment that Lorelai realized she didn't feel any of those emotions with Max.
Her fear instinctively made her call Christopher and the two chatted away like no time went by at all. It was painfully obvious that in Lorelai's time of need, she ran to Christopher — not her fiancé. In the middle of the night, Lorelai called off the wedding and took Rory on a road trip to Harvard.
6 Funniest: Paris As Romeo
In "Run Away, Little Boy," Rory was chosen as Juliet in her school's miniature production of Romeo & Juliet. Unfortunately for Rory and Dean, Tristan was chosen to play Romeo and he took part too seriously. He was going to kiss Rory on the night of the play and enjoy every minute of it.
But when Tristan got into trouble, his dad ripped him out of school. This meant Rory's class had no Romeo. The only person who knew the lines and was brave enough to step up to the plate was the one and only Paris Geller, who told Rory to eat a mint before kissing her in front of everyone.
5 Saddest: Rory & Jess' Car Accident
Jess was the new guy in town and was immediately cast as Stars Hollow's bad boy. He didn't care for school, he was blamed for stealing money from Taylor, and so much more. Luke tried his best with Jess but the only person the young rebel was semi-nice to was Rory.
As much as everyone hated it, Rory gave Jess the benefit of the doubt and started hanging out from time to time. That all came crumbling down, however, in the episode "Teach Me Tonight." Jess and Rory went out for a late-night drive and got in a car accident. Rory ended up breaking her arm and Jess got kicked out of Stars Hollow.
4 Funniest: Sookie & Jackson's Engagement & Wedding
Sookie and Jackson both loved each other more than they were willing to tell the other person. This became clear when they were talking about moving in together, but was even further affirmed during the lunch basket auction in "A-Tisket, A-Tasket."
After Jackson refused to bid on a lunch date with Sookie — because he didn't think she wanted to live with him — the two ironed things out well enough when he proposed! The very idea that they started the day off in an argument over living together and it turned into an engagement is very on-par for Sookie and Jackson. From that day on, they began planning their wedding.
3 Saddest: Lorelai's Graduation
Throughout the first season, viewers saw Lorelai work a full-time job, be a single mother, and tackle night school for a degree. She's a woman who can do it all. Because Lorelai never had a chance to go to college after getting pregnant so young, her graduation day was a monumental moment for her. The only person Lorelai needed at her graduation was Rory.
Alas, Rory messed up hard. Not only did she invite Emily and Richard to the ceremony but she skipped her mother's graduation because she played hooky from school to be in New York with Jess. Lorelai was heartbroken when she looked out into the audience and didn't see her only child.
2 Funniest: Lorelai Hiding From Luke
Lorelai and Rory went to Luke's Diner every day. If they weren't there for their morning coffee, they were grabbing a quick lunch. And if they weren't at Luke's for lunch, they most definitely popped by for dinner. But after Jess and Rory's car accident, Luke and Lorelai went head-to-head over the well-being of Jess and Rory. The fight was so awful that Lorelai couldn't go to the diner anymore!
While the argument in itself was not funny, watching Lorelai try to find a decent coffee in her town was hysterical. She and Rory did everything they could to ignore Luke and his wonderful food until they couldn't take it.
1 Saddest: Richard Retired Without Telling Emily
Richard and Emily were a very propper couple but they've been together long enough that secrets between them seemed impossible. This is why it was torture seeing Richard hide the fact that he quit his job without telling Emily. Emily was blindsided by the decision and hated that he made such a big move without telling her.
Things only got worse for the two because when he retired, Emily and Richard were not used to each other being in each other's space. His retirement made them both unhappy.
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