Dean Forester, Gilmore Girl’s Worst Character

As I sit in my bed, a cup of chai tea in hand, my laptop placed beside me, watching Gilmore Girls, I am in my happy place. I began watching Gilmore Girls at age ten, and today, at age 18, I continue to indulge in each episode, falling harder in love with the town of Stars Hollow and the charismatic citizens who live there with each second watched. I have now watched the entire series of Gilmore Girls an embarrassing amount of times; each time I finish the show, I immediately click back to rewatch the pilot for the umpteenth time. I am addicted to the show: the comfort it brings me, the characters it highlights, and the stories it tells. As a Gilmore Girls connoisseur, I am up to my ears in opinions of this show, specifically on the Gilmores’ love life. 

So let’s begin.

When I began writing this piece, I had planned to discuss each of Rory’s committed relationships, but it seemed I had too many opinions of Dean, and he ended up taking the article. Good going, Dean.

Introducing Dean Forester, the objectively worst boyfriend and possibly character in the entirety of Gilmore Girls. Before I begin demolishing every single aspect of Dean’s character, let’s discuss the Rory-Dean love origin story. Dean and Rory met at Stars Hollow High, where at first glance, they were both encapsulated by each other’s presence. Soon after meeting, Dean became Rory’s first boyfriend. The two were utterly infatuated with each other, spending each moment apart thinking of the other. Dean was a stereotypically perfect first boyfriend; he was nice, loyal, dependable, and cute, very cute. But as their relationship developed and I had reached my approximately seventh time watching the show, red flags began popping up everywhere. 

Red Flag #1 A lack of trust: When Dean first saw Rory, he began following her, watching her every move, and keeping track of her whereabouts. While at first glance this can be thought of as endearing and adorable, it is simply stalker-like. This obsessive behavior continues through the show, as Dean never enables himself to fully trust Rory and doesn’t respect her boundaries. This issue progresses to a point where Dean calls Rory sixteen times in a single night and even follows her to a school project meeting. 

Red Flag #2 Anger issues: Each time an inconvenience occurs, minor or not, he looses control of his emotions, unable to remove himself from the difficult situation, and becoming red in the face in seconds. For example, following Tristan being a jerk to Dean at the school dance, he is unable to just walk away, and instead tells Tristian “I’ll kill you, you idiot!” He often becomes angry at Rory, even for small things like not having time for him because she needs to study or would like alone time. 

Red Flag #3 Sexist: Welcome to the episode that makes me want to break Dean’s heart myself. Oftentimes, Dean and the Gilmore Girls get together for pizza, loads of junk food, and a movie. On this night,  they chose The Donna Reed Show, an American sitcom starring a middle-class housewife as she performs the many stereotypical tasks of a wife in the late 1950s. While watching, Lorelai and Rory make fun of each scene, replacing the lines, highlighting the sexist motives of The Donna Reed Show. Enter Dean, the dark cloud, ruining the supposed-to-be fun evening. Opposed to joining in with the Gilmore girls in laughing at the hilarity of the stereotypes portrayed, he comments he likes the idea of a woman merely acting as her husband’s servant: cleaning, baking, and always having dinner prepared after the husband’s long day at work. He glorifies this sexist stereotype: an ideal that the Gilmores have proudly moved as far away from as possible. As a result of the guilt he inflicts on Rory for not fitting this ideal, she creates an entire production for him, dressed like Donna Reed, cooking him a full meal, pearls, stiletos, and even jello for dessert. 

Now, while all of these things are worth mentioning as they reveal Dean’s flaws, they do not necessarily make him a bad person, just maybe a person who is not yet ready to be in a committed relationship. But these next examples, yea, bad person.

Rory Gilmore was raised by a single mom, Lorelei Gilmore, who got pregnant at age 16 to her father Christopher, who was not active in Rory’s childhood— financially or emotionally. Rory did not grow up in a household where people often said “I love you,” in a romantic way. This idea of romantic love was foreign to Rory and thus scary. She knew her father had told her mother he loved him, and still, he skipped out on the two of them. So, when Dean tells Rory he loves her on their three-month anniversary, she was not prepared to reiterate that sentiment. It scared her, and even though later on she revealed she did love him, at that moment between feelings of shock and fear, she was unable to communicate her emotions. Since she was unable to reciprocate that sentiment, Dean broke up with Rory: leaving her alone just because she was not ready to share her emotions, not even for a moment considering that it may be difficult for some people to vocally express their deepest feelings. Even after months of reflecting, Dean does not get back with Rory until she finally confesses her love.  

Soon after Dean’s second breakup with Rory, Dean meets Lindsey Lister, a seemingly decent person and former friend-ish of Rory. At the young age of 19, the two get married. While this all seems good, the night before his wedding, a drunk Dean confesses to Luke Danes, another iconic citizen of Stars Hollow, that he is still in love with Rory, commenting on her “pretty hair” and intelligence. Despite these evident emotions, he follows through with the marriage, a testament to his immaturity and inability to be alone. Not even to mention how unfair this is to Lindsey, who is in love with a man who she believes to be a perfect husband. 

We have finally arrived at the moment that defines Dean as a god-awful individual. As said previously, Dean entered his marriage to Lindsey uncommitted and still harboring feelings for Rory. As Dean and Rory begin seeing each other more often once Dean starts working as a construction worker for Lorelei’s inn, the two begin to rekindle past feelings. On the night of the Inn opening, due to random circumstances, the two end up alone at Rory’s house. Then, Dean cheats on Lindsey. Dean rejects his vows as a married man, hurting Lindsey, and ruining a family. I am not exempting Rory from being at fault at this moment because it takes two to cheat, but Rory did not have an ethical or moral responsibility to another person. The worst part of this situation was that when Dean returned home, he yelled at Lindsey, taking out his personal guilt and anger on her and leaving her feeling as if she had done something wrong. 

So now, over 1000 words later, I have at least begun to detail why Dean Forester is the curse that plagues Gilmore Girls; the wound on an otherwise perfect body; the crack of paint in the Sistine Chapel.

• fall
• Gilmore Girls
• Lorelai Gilmore
• romance
• rory gilmore