As one of the most beloved hit series of the early 2000s, Gilmore Girls defined a large part of the millennial television-watching generation. Through its loving depiction of small town life in Stars Hollow, Connecticut, and its creation of some of the most vibrant characters in the history of young adult television, the series remains just as adored and relevant today as it was when it first premiered 20 years ago.
A large part of what makes the series so highly beloved and discussed is the character of single mother Lorelai Gilmore, portrayed brilliantly by Lauren Graham. Though Lorelai is by far one of Gilmore Girls' best characters, even the strongest of characters are subjected to storylines that would have been better left unexplored. Here's a look back at Lorelai's best and worst plots in the series.
BEST: Her relationship with her parents
Every series needs a good source of conflict, and for Gilmore Girls, that conflict comes in the clash of worlds, views, and values between the open-minded, independent Lorelai and her conservative, judgmental parents Richard and Emily.
The dynamics between these three characters change quite a lot over the series' seven seasons, but Lorelai is always at her most dynamic, her most compelling, and her most fully dimensional whenever her storylines center around her conflicts with her parents' high society world and what they expect of her.
WORST: Her relationship with Jess
First impressions may go a long way in determining how two people will (or won't) get along. But even if that's true, there's no way to claim that Lorelai's relationship with Jess doesn't feature some of her most petulant and stubborn moments.
Because of the snap judgment she makes of Jess's character in their first meeting, Lorelai treats him rudely and judges him at every possible occasion during the remainder of the series - even long after Jess has cleaned up his act and become an upstanding citizen. She ignores every possible opportunity to see points of similarity between them, even once he becomes her nephew by marriage.
BEST: Finding herself
Regardless if Gilmore Girls purists liked the Netflix revival A Year in the Life or not, one of its strongest storylines featured the emotionally adrift Lorelai taking some much needed time to find herself and figure out what she wanted with her life as she reached middle age.
The journey, both literally and internally, allowed Lorelai to figure out what she wanted in her relationship with Luke, to make peace with her relationship with her late father, and to come to with all of the emotions she'd been struggling to keep bottled up over the last year.
WORST: Her relationship with Dean
While her relationship with Rory's boyfriend Jess featured Lorelai at some of her judgmental worst, it's her creepy, secret bond with Rory's first boyfriend, Dean, that truly puts us off even more. After initially refusing to like Dean for all he represented in a quickly growing up Rory's life, Lorelai came to be a staunch defender of the overbearing teen.
So staunch a defender, in fact, that she formed a secret friendship with Dean behind Rory's back, meeting with him and offering him tips and secret advice regarding their relationship and Rory's growing friendship with Jess.
BEST: Earning her business degree
After Lorelai Gilmore became pregnant at a very young age, she didn't go on to have the traditional education experience and career path that her parents expected of her. But as an adult, she took the initiative to advance her career in running an inn by pursuing her business degree through night classes.
The storyline allows for some of the subtlest moments of character growth for Lorelai and her parents both, particularly when they attend her graduation, and all three Gilmores are allowed a glimpse of the life that could have been.
WORST: Dating Digger Stiles
Gilmore Girls may be well known for its soapy teen romances, but one of the soapiest and worst of them all involved Lorelai reconnecting with a familiar face from her own adolescence, Jason "Digger" Stiles.
Given the series' tendency to focus on Lorelai's tug of war between the upper class world of her parents and the lower middle class world of her life in Stars Hollow, it makes sense for her to have love interests that traverse those boundaries. However, Digger is a permanent manchild and their total lack of chemistry makes it impossible to invest in their far too long relationship.
BEST: Opening the Dragonfly Inn
It was always Lorelai's dream to someday run an inn of her own, after all her years of experience at the Independence Inn. For that reason, it's no question that seeing her make that dream a reality is one of the series' most satisfying storylines of all.
With the help of her friends and business partners Sookie and Michel, as well as the of Luke, Rory, and her parents, Lorelai is finally able to make one of her longest dreams come true in the series' fourth season, culminating in a truly incredible launch in the fourth season finale.
WORST: Feuding with Rory
The series may have fully gone off the rails in its final season, but the groundwork was laid long before that with the disappointing and completely frustrating storyline that found Rory and Lorelai at odds with one another for most of the series' sixth season.
Both women came across as totally stubborn and childish, and the storyline felt entirely against the inherent nature and heart of the series. It's a plot that benefited no one in the end, and certainly ranks among Lorelai's worst.
BEST: Making amends with Emily
It's hard to find many moments over the course of the original series' run when Lorelai and her mother are on the best of . Even throughout much of the revival series, they are at odds with one another, warring in therapy sessions and avoiding taking responsibility for any of the faults in their relationship.
But over the course of the miniseries, through therapy and apart from it, these two women find a common ground - if not for a full establishing of a bond that had never been there, then at the very least for a meeting of the minds to a degree which they'd never been able to reach.
WORST: Marrying Christopher
Does this one really need all that much explaining? From day one, the relationship between Lorelai and Christopher was completely toxic, and represented one of the series' biggest failings.
It's all good and fun to idealize a high school romance, particularly since Lorelai was emotionally stunted in many ways for much of the series' duration. But to have her fundamentally revolt against her character's nature in the oft-ignored final season, and elope with Christopher in Paris with no one else around, represents one of the series' biggest insults to her character.