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Gilmore Girls followed Rory Gilmore and Lorelai Gilmore’s lives at a pivotal time. During the show’s seven-season run, Rory graduated high school and college, and Lorelai grew and expanded her career. Richard Gilmore and Emily Gilmore experienced change, and so did Lane Kim. With big changes often come mistakes, though. We’ve collected three Gilmore Girls mistakes that altered the characters’ lives.  

Rory Gilmore shouldn’t have turned down the job in Rhode Island 

In season 7 of Gilmore Girls, Rory Gilmore had some difficult decisions to make. With a job offer in hand, the always cautious Rory made a rather unexpected decision. She turned down a job at a Rhode Island newspaper to await word on a competitive summer fellowship with the New York Times. 

'Gilmore Girls' actor Alexis Bledel as Rory Gilmore sitting at a desk in a scene from 'Gilmore Girls: A Year in the Life'
Alexis Bledel as Rory Gilmore in a scene from ‘Gilmore Girls: A Year in the Life’ | Neil Jacobs/Netflix

Rory ultimately didn’t get the fellowship and didn’t have a job upon graduating from Yale. The decision turned out to be a critical mistake. Rory struggled to find long-term employment and was still directionless in Gilmore Girls: A Year in the Life. Taking the job at the Providence Journal might have changed everything. Gilmore Girls fans are largely frustrated by the mistake.

Richard Gilmore’s decision to badmouth Jason Stiles was a ‘Gilmore Girls’ mistake

Richard Gilmore left his job with Floyd Stiles and started his own insurance business. Eventually, Floyd’s son and protege, Jason Stiles, asked to go into business with Richard. While Gilmore Girls fans have mixed thoughts about Jason, he was a solid worker and seemed pretty ethical. He did his job well. His only real mistake was secretly dating Lorelai Gilmore. 

'Gilmore Girls' actor Alexis Bledel as Rory Gilmore touching a wall-size portrait of Richard Gilmore (Edward Herrmann)
‘Gilmore Girls’ | Saeed Adyani/Netflix

When Floyd threatened to sue Richard and Jason, Richard folded and went back to Floyd’s business. The decision was understandable. Richard was protecting his financial interests. He didn’t need to badmouth Jason, though. The decision was a critical mistake. While his relationship with Lorelai ultimately recovered, Richard knew badmouthing Jason would have consequences for Jason and Lorelai’s relationship, and he just didn’t care. It made him seem petty and unprofessional. 

Lane Kim should not have accepted Zack’s proposal 

Lane Kim was destined for big things, insist Gilmore Girls fans. She was talented, spunky, and driven. If given the opportunity, we believe Lane could have found her way into the music industry in some capacity. That all came crashing down when she agreed to marry Zack Van Gerbig. Lane should have never accepted his proposal. 

Lane Kim and Rory Gilmore in 'Gilmore Girls: A Year in the Life'. The friends were at the center of several seriously problematic 'Gilmore Girls' moments
Lane Kim and Rory Gilmore | Saeed Adyani/Netflix
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We aren’t saying Zack wasn’t a nice guy in many ways. He could be sweet to Lane, but he lacked drive and ambition. Lane’s marriage to Zack guaranteed she’d be stuck in Stars Hollow for the rest of her life. We think she deserved more than that. It was the most disappointing critical life mistake in Gilmore Girls.