Three Men and a Rory: How Rory Gilmore Was Actually the Problem

Despite the harshness of the title, it’s important to disclose the fact that I am a Gilmore Girls fan. I began watching it with my mother when I was 13, during the pandemic, when she saw a resurfaced tweet from Lin-Manuel Miranda raving about the show. And since we also loved Hamilton, we decided to heed Lin-Manuel’s advice and give the show a shot. It became yet another thing that we bonded over as we saw much of our own dynamics and conversations represented in the iconic mother-daughter duo. Despite the obvious line between real life and fiction, Rory and I shared similar sentiments towards our mother. As Rory said in her graduation speech, “My mother never gave me any idea that I couldn’t do whatever I wanted to do or be whomever I wanted to be.” After our first watchthrough, Gilmore Girls instantly became a staple at our house. It’s our most rewatched show, and we always seem to find our own sense of comfort within it. 

That being said, being part of a fandom should not reduce one’s ability to be objective about distasteful behaviors. The show goes the extra mile to write characters that ask us to forgive a lot of their wrongdoings because of their sympathetic nature and charisma. This is especially true of the younger member of the Gilmore Girls pair, Rory Gilmore. For the first four and a half seasons (up until she gets a certain haircut), Rory is bookish, ambitious, and idealistic, but like any well-rounded character, she’s flawed. As she gets older, Rory struggles with introspection and loyalty. She becomes self-centered and reckless. The young girl who had such a bright future with strong ambitions becomes a shell of who she could’ve been. All the while leaving a trail of broken hearts in her wake. 

Gilmore Girls aired during the 2000s when rom-coms like How to Lose a Guy in 10 Days and The Wedding Planner were at an all-time high. The show depicted how the women navigated their relationships with friends, families, and ultimately with men. The phrase “romantic chaos” does little to fully encapsulate the three famous relationships that played out on the hit show. Ever since it started and ended, fans from all walks of life have had heated debates over who was the best or worst boyfriends: Dean, Jess, or Logan. While I personally found myself rooting for all of them at different points of the show, I think it’s important to acknowledge that Rory wasn’t some innocent little princess who just fell into her situations. She was complicit in how every one of her relationships began and ended. Rory often demonstrated self-centered behavior and avoided accountability so much so that when she began to get in relationships with them, they all had at least one moment to call out her unfair behavior and watched her respond with deflection and flustering. 

Let’s break down the relationships one by one, starting with Dean Forester. Played by Jared Padalecki, Dean is Rory’s first-ever boyfriend. He begins as a kind and devoted young man who tries to engage with Rory’s interests, i.e., reading and watching classic films; he tries to get on the good side of her well-to-do grandparents, and most importantly, ingratiates himself with her mother. When Rory begins to detach from him emotionally, because of an intimate awakening with Jess, Dean becomes increasingly more possessive and insecure, leading to a very public breakup. Rory, in an attempt to clear her conscience, after months of gaslighting, offers Dean an awkward, clumsy apology, to which Dean responds, “Well, too bad, Rory. Somebody doesn’t like you for once” (Season 3, episode 8). In this moment, Dean not only regains some dignity from this breakup, but it also conveys the point that to love someone doesn’t mean enduring humiliation. Many things have been said about Dean throughout the entirety of the show, but the bottom line is that he deserved basic respect from Rory. 

The second boyfriend on the roster is the monosyllabic, brooding “bad boy” played by Milo Ventimiglia, Jess Mariano. Jess, who’s new in town, enters the scene in season two. From the beginning, he’s the quintessential rude boy, who disrupts the moderately calm environment that the show is known for. It doesn’t take too long before Jess sets his sights on Rory, despite her already being with Dean. Jess downplays his intelligence just enough not to be the center of attention and plays into the “I-hate-everyone-but-you” trope, which ultimately won Rory over. Even though a lot of Gilmore Girls fans are “Team Jess”, I feel that many of them ignore the fact that their relationship was built on betrayal and disloyalty; Rory was cheating on Dean with Jess. Although the terms of their relationship were unclear, Rory presumed that Jess was going to make himself available to her and not see other people. During a childish confrontation where Rory lets her hypocrisy show, Jess retorts with, “I’m sorry, did I hear from you at all this summer?” (Season 3, episode 2). This was the beginning of a new dynamic for the two. On the one hand, Jess had to use more than two words to express himself, and on the other hand Rory had been brought down to Earth…briefly. And like many rocky foundations, eventually it all came crashing down.

 A few seasons, a Yale acceptance letter, and a bad haircut later, we finally meet Logan Huntzberger, played by Matt Czuchry. Logan is the personification of privilege; born and raised into wealth, he has a cocky personality and a sarcastic sense of humor that even rivals Lorelai’s. Even though she tried to fight the attraction she felt, Rory enjoyed the attention Logan gave her. She enjoyed the way that he could show her off at fancy events and relished the social and monetary benefits that came with being a Gilmore at Yale. All the while denying that she had the same privileges as Logan and his friends. Logan calls out this hypocrisy during a confrontation about privilege by saying, “Well, you’re not exactly paying rent either” (Season 7, episode 8). Despite attending a prep school and being accepted into the top Ivy League schools in the country, Rory still, in part, viewed herself as a small-town girl who never left. But in reality, she was very different. She attended parties, drank, socialized with other wealthy college kids, and even broke the law with them.

Beyond the hypocrisy, Rory was, in reality, a very non-committal person. She struggled to say “I love you” in every single relationship. She struggled to stand firm in her values and allowed herself to be swayed by the priorities of the men in her life. This raises the question: How can a character lauded for her ambition and ethics be so flimsy when it comes to her own personal boundaries and genuine wants for her relationships? I believe this is where we must address the Palladino in the room. Amy Sherman-Palladino is the mind behind Gilmore Girls and The Marvelous Mrs. Maisel. Both shows center sarcastic, independent, and headstrong women who often come undone in moments of emotional vulnerability, leaving their partners with a lot of heartbreak and disappointment. Rory is just one of the many archetypes that Amy Sherman-Palladino clearly likes writing about: The fall from grace of a beloved character who had everything at her disposal, who could’ve done everything she dreamed of and more. 

Alas, while the writing definitely contributed to Rory’s portrayal and her behaviors towards her boyfriends, as viewers, we also have to take responsibility for the fact that we don’t like seeing thoroughly flawed characters. Perhaps it reminds us of our own fallibility. Perhaps, we insert ourselves so deeply into things that we take it personally when a character, like Rory, makes a decision that we, otherwise, wouldn’t have made. Was Rory a perfect daughter, friend, or girlfriend? Of course not. But that was set in stone from Palladino’s writers’ room. Still, I think we can all agree that Rory should not have gotten that haircut in season four. 

• Dean
• Gilmore Girls
• jess
• Logan
• rory gilmore