Warning: Spoilers ahead for Gilmore Girls!
Arguably, one of the most interesting aspects of Gilmore Girls is the depiction of the show of the complex and nuanced decisions of life. Gilmore Girls is full of significant life events for all its main characters. The show’s storyline features a series of broken engagements, cheating scandals, last-minute college decisions and more, all of which impact the show’s conclusion. Some of the choices are made as a result of years of character development, while others are just mistakes made on pure impulse.
On my annual rewatch of Gilmore GirlsI can’t help but wonder about some of the moments in it Gilmore Girls Seven season run, given that some easily could have been avoided. If other decisions are made, certain letters in Gilmore Girls could have led very different lives, creating all sorts of interesting, what-if scenarios.
10
When Rory almost went to Harvard instead of Yale
For Rory’s whole life, she wanted to go to Harvard
If Rory Gilmore had gone to Harvard University, her lifelong dream school, her arc as a character on the show would have looked much different. If Rory had gone to Harvard, she would never have developed her close friendship with Paris Geller (Liza Weil) after high school. She also would never have met her last boyfriend Logan, who she is still involved with years later Gilmore Girls: A Year in the Life. While Yale gave Rory two deeply important relationships, it also altered the course of her life in a potentially negative way.
Logan Huntzberger’s father, Mitchum, is a powerful media mogul who gives Rory a local internship after learning about her journalistic aspirations. Despite the fact that he gave her the opportunity, he also told her that she “just don’t have it” To make a career in journalism. If she hadn’t gone to Yale and dated Logan, I think Rory could have pushed her journalism career further at Harvard apart from family influenceAnd without Mitchum’s heavy criticism. At the same time, without Rory at Yale, Paris may never have met Doyle, whom she later marries, and Logan Huntzberger may have become a lifelong playboy.
9
When Lorelai almost married Max Medina
If Lorelai had married Max, she would never have realized her feelings for Luke
Lorelai Gilmore dated Rory’s Chilton Academy teacher, Max Medina. When he initially proposes to her, partly out of jealousy over her friendship with Luke, Lorelai, in her typical fashion, dives into a dignified hyperbolic explanation of what a proper proposal should look like – including – A thousand yellow daisies. To make up for his hasty proposal, Max literally places 1,000 yellow daisies around the town of Stars Hollow, including Lorelai’s workplace at the Independence Inn.
The grand gesture finally wins Lorelai over, and she accepts his proposal, but later abruptly breaks it off. While I thought this breakup was devastating, it also makes way for Lorelai’s strongest relationship on the show — her later romance with Luke Danes (Scott Patterson). Luke has long been an amazing friend to Lorelai and a father figure to Rory, and if Lorelai married Max she may never have found her way to Luke in the end. On Luke’s end, he could have remained in a loving marriage with Nicole, or remained a lonely man living above his servant.
8
When Christopher goes back to Sherry because she is pregnant
Lorelai could have married Christopher much sooner if he hadn’t gone back to Sherry
Christopher Hayden, Rory’s father has a complicated relationship with Lorelai. When Lorelai becomes pregnant with Rory, her family insists on supporting them as long as she marries Christopher. Feeling pressured, Lorelai flees to Stars Hollow, working her way up at the Independence Inn and finding a supportive community among the townspeople. The pair reunite in season 2 when Christopher vows to be a more present father to Rory, and his newfound commitment to getting his life in order attracts Lorelai.
As their relationship progresses, his ex-girlfriend Sherry calls Christopher while he is with Lorelai to let him know she is pregnant. Regretting not raising Rory, Christopher immediately decides not to make the same mistake, and goes back to Sherry. If Sherry wasn’t pregnant, I still think Christopher and Lorelai would have been a bad match, despite their history. While Christopher and Lorelai briefly marry later in the show, I think a wedding at this point in the series would have resulted in a much more volatile and consequential breakup because Rory is still in high school.
7
When Jess left for California
If Jess stayed in Stars Hollow he might have ended up with Rory, but with less character development
Jess Mariano (Milo Ventimiglia) comes to Stars Hollow as a troubled teenager from New York City. His mother sends him to live with his uncle, Luke Danes, in the town to prepare him. Despite his resistance tendencies, he is highly intelligent and shows a literary flair despite his poor conditions at school. His interest in literature and willingness to understand Rory are what draw her to him – while she is still dating her first boyfriend, Dean Forester (Jared Padalecki), which causes their breakup.
After Rory begins a relationship with Jess, he is supportive of her Ivy League dreams and initially enjoys spending time with her. However, she quickly realizes that his lack of regard for his future and eventual lack of effort in their relationship is a deal breaker. When Jess’ father tracks him down to Stars Hollow, Jess leaves for California to get to know him, leaving Rory on graduation day. Jess returns to Stars Hollow a year later to confess her feelings for Rory.
If Jess hadn’t left for California, the couple might have ended up together, because Rory wouldn’t have pursued Logan at Yale instead, and the couple might have ended up on a similar emotional playing field. However, Jess’ time in California also provided some much-needed character development, viz He returns to the East Coast years later as a published author with a stable life in Philadelphia. Had he never left, he would have remained profoundly emotionally immature and never realized his own dreams of becoming a writer, a trait Rory attributes to her lack of perspective.
6
When Logan proposes to Rory before Yale graduation
If Rory had said yes to his proposal, she would have had a happier ending
When Rory and Logan are about to graduate from Yale and Logan has the opportunity to pursue his tech company in San Francisco, he proposes to Rory, encouraging her to join him in California to start her own career in journalism. Rory ultimately turns down the offer, as she doesn’t want to commit to anything post-grad and wants to have her career options. “Way Open” and married Logan and his family.
How viewers learn from A year in the lifeRory’s career is floundering and inconsistent, and she struggles to maintain meaningful relationships. Years down the line, she is still having an affair with Logan, despite his engagement to someone else. If Rory accepted the offer, I think she would have been more successful and lead a more fulfilling life. With Logan’s family connections and a change of scenery, Rory could have had a shot at the success that she always self-sabotages.
5
When Luke divorces Nicole
Luke could have settled for her
After a neighborly dispute with cantankerous town selectman Taylor Doosey, Doosey hires a lawyer to settle it. The lawyer is Nicole Leahy, who begins a relationship with Luke that ends in a drunken wedding on a cruise ship. While the couple attempts to make their relationship work, it’s clear that Luke still loves Lorelai, and his marriage to Nicole ultimately crumbles when she cheats on him. If Nicole hadn’t cheated, I think Luke might have tried to stick it out with her due to his honor and his stubborn nature, That would have prevented him from finally finding happiness.
If his character hadn’t gone through the divorce and realized what he really wanted from a relationship he had with Lorelai, the show’s most beloved couple would never have come to be.
Luke’s divorce was also another sign that his relationship with Lorelai, at this point platonic, was always paramount to him. If his character hadn’t gone through the divorce and realized what he really wanted from a relationship he had with Lorelai, the show’s most beloved couple would never have come to be.
4
If Lorelai never asked her parents to finance Rory’s Chilton tuition
The Friday night dinners are one of the hallmarks of the show
The show begins with Rory’s acceptance to the prestigious Chilton Academy, which has a hefty tuition price tag. Lorelai is only able to cover part of the tuition, and begrudgingly asks her parents to help with the costs. Lorelai has a complicated relationship with her parents, especially her mother, Emily (Kelly Bishop) who often expresses disappointment in Lorelai’s life choices, but Lorelai reaches out to them for Rory’s sake.
If Rory had stayed in public school, the show would have lacked a lot of character and plot development. A major part of the show is exploring the generational trauma of Lorelai’s teen pregnancy and the different life she hopes to give Rory, and the Chilton era of the show illustrates that. The show also would have lacked her infamous Friday Night Dinner scenes, which are often pivotal moments in the show’s plot and full of sharp dialogue.
3
If Emily and Richard never got back together
The couple separated for a short time
Emily and Richard briefly separate, which finally allows Emily to find her purpose after feeling so connected to Richard for her entire life. A breach of trust over a business decision coupled with Emily often feeling overlooked sparked some much-needed time apart. When the couple reunites and renews their vows, Rory is her grandfather’s best wife, where Logan Huntzberger is also present.
The wedding was a pivotal moment in Rory’s relationship with Logan and a moment of growth for Emily and Richard. The couple’s reunion also made Richard’s death in the reunion much more devastating, but also created the beautiful conclusion that while A large part of Emily was defined by her marriage, her purpose extends far beyond. If the separation period and subsequent renewal of vows never occurred, the storyline of the strength of the women of the Gilmore family would not have packed as much of a punch.
2
If Dean never married Lindsay
Dean may have held Rory back from her aspirations
Dean had never understood Rory’s academic pursuits as much as her other boyfriends, and their separation in Jess’s wake was a blessing in disguise. Dean marries his high school girlfriend Lindsay (Ariel Kebbel) at a very young age, and proceeds to cheat on her with Rory, which he never really gets over. In the process, they both brutally hurt Lindsay, who discovers their affair in a public way that the whole town knows about.
At the same time, if Dean never married Lindsey, there is a chance that Rory would have stayed with him and Never pursued her dreams because of his weak masculinity and jealousy issues. While Rory was also involved in the affair, Dean’s emotional immaturity far exceeded Rory’s, and I think their relationship would have taken a big toll on her life. Rory always had aspirations of finding a life partner to support her lofty visions for her future, and Dean wouldn’t be the man.
1
If Jess never came to visit Rory years later
Jess encourages Rory to return to Yale after taking a leave of absence
When Rory steals a yacht with Logan on a bender after Mitchum’s harsh journalistic criticism, she takes a leave of absence from Yale to complete her court-ordered community service. During this time, Rory goes to live with her grandparents in Hartford, where she assists Emily with her Daughters of the Revolution (DAR) events and continues to date Logan. During the period in which Rory is missing, Jess returns to Connecticut to pay Rory a visit while he is in town to see his Uncle Luke. Jess is much more mature than when he left Stars Hollow.
As he always supported Rory’s academic efforts, he is shocked and upset that Rory dropped out of Yale and is dating Logan, who lets his ego get the best of him when he meets Jess. In the famous dinner scene, Jess delivers a now highly quotable monologue.
I think that if Jess hadn’t swooped in to snap Rory out of it at that moment Gilmore Girls, She may have given up completely. Rory has a history of struggling to handle criticism about herself, but Jess remains the only person to get through to her, making this moment a major turning point in the series.