8 Times Rory Seriously Messed Up In Gilmore Girls

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Gilmore Girls never shied away from putting its characters in difficult situations and making them react like real, imperfect people, but the show might have gone too far with Rory. The youngest Gilmore made so many mistakes that it was impossible to keep track of them. Rory was always made out to be the ultimate good girl — she was a book-loving perfectionist who loved planning and organizing, she got straight As and was accepted into the best educational establishments, and she was a calm and collected individual with principles. In reality, Rory didn’t mind throwing her principles out the window on more than one occasion.

While some of Rory’s mistakes were relatively small and could be easily forgiven, like that time she slept in and missed her English test, others were much graver in their nature and made Rory utterly unlikable, like when she repeatedly cheated on her boyfriend with Logan and didn’t seem to regret it one bit. Gilmore Girls didn’t strive to only show people at their best; instead, it presented characters as flawed human beings, which was why the show was so relatable in the first place. Still, the series might have overdone it with Rory and her continuous mess-ups that she didn’t seem to learn anything from.

RELATED: 8 Mistakes Gilmore Girls Season 9 Needs To Fix, If It Ever Happens

8 Rory Didn’t Show Up For Lorelai’s Graduation

“Lorelai’s Graduation Day” (Season 2, Episode 21)

In Gilmore Girls season 2, episode 21, “Lorelai’s Graduation Day,” Rory proved how head over heels she was for Jess when she skipped school and went to New York to see him. That would have been a sweet teenage crush moment if Rory hadn’t missed her mother’s graduation for it. Rory knew when Lorelai’s ceremony would take place, and she was well aware that she would be cutting it very close. Rory ended up taking the wrong bus, so she wasn’t able to make it. She was beating herself up about it later, and Lorelai forgave her, but choosing a guy over her mother was still a jerk move on Rory’s part.

7 Rory Cheated On Dean With Jess

“I Can’t Get Started” (Season 2, Episode 22)

Rory and Jess' First Kiss at Sookie and Jackson's Wedding in Gilmore Girls Season 2

Evidently, Rory’s string of epic failures was just getting started because in the very next Gilmore Girls episode, “I Can’t Get Started,” she made her emotional affair physical by kissing Jess at Sookie and Jackson’s wedding. Rory and Dean’s relationship was declining fast, and Rory had already been into Jess for some time. Still, it was one thing to just spend time with a guy who was not her boyfriend, and it was another to kiss him while still dating someone else. This was one of many affairs that Rory would partake in, and it all seemingly began with her feelings for Jess.

6 Rory Fat-Shamed A Ballerina

“Die, Jerk” (Season 4, Episode 8)

Rory Doing A Review in Gilmore Girls

Rory was known for her quick wit, especially when it came to her writing. However, Gilmore Girls season 4, episode 8, “Die, Jerk,” didn’t showcase her journalist sense of humor, but instead, painted Rory in very dark colors. The editor of Yale’s newspaper demanded that Rory write an opinionated piece, and for some reason the young journalist took it as a suggestion to fat-shame a ballerina while reviewing her performance. Rory called the woman “a hippo,” which led to a nasty confrontation, but Rory deserved it. Gilmore Girls‘ “Die, Jerk” hasn’t aged well, and sadly, it is not the only episode to be deemed problematic in retrospect.

5 Rory Slept With A Married Dean

“Raincoats And Recipes” (Season 4, Episode 22)

Rory and Dean in Bed Kissing in Gilmore Girls

In a situation reversed two seasons later, Dean was the cheater, Rory was the accomplice, and Jess was innocent. In Gilmore Girls season 4, episode 22, “Raincoats and Recipes,” Rory decided to lose her virginity to Dean, and yet there was a catch — he was now married to Lindsay, although obviously theirs was not a happy union. Not only did Rory become the other woman and hurt Lindsay, but she also didn’t regret her actions one bit in the next episode when Lorelai told her off. Rory believed that she was entitled to Dean because she was his girlfriend first, and that was ultimately her worst mistake in the entire series.

4 Rory Stole A Boat With Logan

“Blame Booze And Melville” (Season 5, Episode 21)

Rory and Logan Stealing a Yacht on Gilmore Girls

In Gilmore Girls season 5, Rory was spiraling out of control, reliving the wild teen years she had never had in her young adulthood, and Logan’s bad influence only made matters worse. In season 5, episode 21, “Blame Booze and Melville,” Rory found Logan at a party and asked him to steal a boat with her just for the fun of it. This storyline served as evidence of Rory going down a darker path, but at least this time, there were consequences — Rory got arrested and had to do community service. The boat incident made little sense in terms of Rory’s story arc, but it was her biggest run-in with the law.

3 Rory Dropped Out Of Yale

“A House Is Not A Home” (Season 5, Episode 22)

Following the boat fiasco, Rory might have thought that she hadn’t done enough, so she decided to drop out of Yale in the very next episode, “A House Is Not a Home.” It was understandable why Rory thought it was easier to blame all her problems on the challenging university, but it was still wrong. In the end, this Gilmore Girls episode marked the beginning of Rory and Lorelai’s most serious falling-out since Lorelai wasn’t willing to accept Rory’s decision to throw away her future. Weirdly, her parents, Emily and Richard, did support Rory and even offered to move in with them for the time being.

RELATED: 20 Gilmore Girls Moments That Made Fans Cry

2 Rory Dismissed A Great Job Opportunity

“Hay Bale Maze” (Season 7, Episode 18)

Rory, Logan, and Lorelai Cheerful in Gilmore Girls

Rory made the strangest, most illogical career decisions throughout her life, but rejecting a job offer at the Providence Journal Bulletin for a mere chance to be part of the New York Times topped them all. In Gilmore Girls season 7, episode 18, “Hay Bale Maze,” Rory was on the fence about a major job opportunity. She was stressing out herself and everyone around her, only to turn down the offer in the end. Rory’s poor decision-making skills and sense of entitlement didn’t do her any good — she continued to sabotage her career in Gilmore Girls: A Year in the Life’s episode, “Spring.”

1 Rory Had An Affair With Logan

Gilmore Girls: A Year in the Life

Rory Smiles at Logan While He Fixes His Tie in the Gilmore Girls: A Year In The Life Episode

Rory and Logan’s relationship timeline was messy to begin with, but it only got worse in the revival series, Gilmore Girls: A Year in the Life. Years after turning down Logan’s proposal, Rory found herself back in his arms, but now he was engaged, and she was two years into a relationship. It seemed like Rory had never learned her lesson about cheating, as she showed no sign of remorse about sleeping with Logan. Unlike the situation with Dean, this affair had consequences: Rory later discovered that she was pregnant. According to the Gilmore Girls costume designer, the father of Rory’s baby was Logan.

  • Gilmore Girls Poster

    Gilmore Girls

    Release Date:
    2000-10-05

    Cast:
    Lauren Graham, Scott Patterson, Sean Gunn, Keiko Agena, Matt Czuchry, Alexis Bledel, Yanic Truesdale, Kelly Bishop, Melissa McCarthy, Edward Herrmann, Liza Weil, Jared Padalecki, Milo Ventimiglia

    Genres:
    Comedy, Drama

    Seasons:
    7

    Summary:
    In the fictional town of Star’s Hollow, single mother Lorelai Gilmore raises her high-achieving teenage daughter Rory. Mother and daughter rely on each other throughout their own life changes, romantic entanglements, and friendships.

    Story By:
    amy sherman-palladino

    Writers:
    Amy Sherman-Palladino

    Network:
    The WB

    Streaming Service(s):
    Netflix

#Times #Rory #Messed #Gilmore #Girls

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