Who’s the Best Gilmore Boy?

Fall has officially arrived, and along with it comes the pumpkin patches, the apple-picking, the corn mazes, and of course, the Gilmore Girls show marathon. It seems to be a universally accepted opinion that autumn is the season of Lorelai and Rory, the central mother-daughter duo of the show. With its small-town setting, unhurried pace, and nostalgic warmth, Gilmore Girls has become a shared comfort show among fans and critics. What seems to be a topic of debate within this popular show, however, is Rory’s taste in guys. 

Throughout the 7 seasons and 154 episodes, Rory went through several phases as she transitioned from her teenage years into adulthood. Between her teenage years as an innocent, bookish high schooler and her adulthood as a problematic Yale student, she encountered several boys, each of whom affected her life in various ways. Whether they influenced her positively or negatively is a subject hotly discussed among the show’s enthusiasts. Who was her best boyfriend? Who ruined her character? Each fan may hold his or her own opinions on these questions, with some being rather extreme. As these feelings are solely subjective, I can only provide my own insights into their personalities and motives regarding Rory. I must warn, however, that my views are not free from bias, so take my commentary with a grain of salt. 

Boyfriend #1: Dean Forester

Where should we even start with Dean Forester? The beginning, of course, for Dean was Rory’s first boyfriend, her “first love.” As with all first loves, their relationship was one defined by unmatured and innocent affection for each other. They first met each other at Stars Hollow High, when Dean was known as the mysterious, attractive new kid. With his height, sleek hair, and classic leather jacket, I wouldn’t blame Rory for falling in love at first sight. Initially, their relationship seemed off to a steady start with each lover being infatuated with the other. Dean was a stereotypically perfect first boyfriend: he was loyal, caring, and dependable, and, most importantly, he built her a car. But even then, several red flags were already beginning to pop up. 

For one, Dean was overly protective of Rory before, during, and even after they dated. From the first moment he set eyes on Rory, he began following her and keeping track of her daily whereabouts, ensuring that he could catch the same morning bus as her each day. Adorable, right? If it were not for his attractive appearance, we would have quickly called him out as a stalker. His obsessive character quickly developed once he realized he had secured Rory as his girlfriend. This, along with his jealousy, prevented him from fully trusting Rory. He proved numerous times during the show that he could not respect Rory’s boundaries. Not only did he attempt to call her sixteen times within a single night, but he also followed her to her school project meeting. His immaturity only got worse as other boys began showing interest in Rory. In his defense, perhaps we all get a little jealous when we see our partner talking with a potential rival, but his actions went beyond the acceptable limits in a healthy relationship. At Rory’s first dance, Dean met Tristan Dugray, who clearly had “a thing” for Rory. Instead of controlling his emotions, Dean chose to escalate the situation and ended the confrontation by telling Tristan, “I’ll kill you.” Now, I don’t know about you, but I would not be comfortable staying in a relationship after hearing that. As much as he might have been joking, it perfectly captured his personality as an overbearing boyfriend with anger issues. Each time a minor inconvenience occurred, Dean was unable to act rationally and resorted to aggression instead. 

Related to this was his inability to take “no” as an answer and his assumption that he is the center of Rory’s world. Whenever Rory wanted to spend time by herself, whether it was because she had to study or simply because she needed alone time, Dean would blame her for not making enough time for him. He became angry when he found out that Rory was planning to attend Harvard, and he begged her to disregard her dreams and remain in Stars Hollow with him. “Hey, I’m not going to Harvard. I could care less about Harvard,” he cried. Sorry, Dean, but the world doesn’t revolve around you. Not only was he acting incredibly selfish, but he was also holding Rory back from her future. Healthy relationships require mutual encouragement and growth, and Dean was doing the exact opposite. Later, on their three-month anniversary, Dean broke up with Rory because she was unable to say “I love you” back, leaving her because she was not ready to make this commitment and open up about her feelings. He did not consider the fact that it may have been difficult for her to express her emotions, especially given the pressure she felt in their relationship. Once again, Dean demonstrated his inability to understand perspectives different from his own. 

Despite all the potential he had, Dean turned out to be nothing but an aggressive and jealous teenage boy. 

Boyfriend #2: Jess Mariano

Jess Mariano entered Rory’s life during her first relationship with Dean, having been sent by his mother to live in Stars Hollow with his uncle, Luke. Originally, I was not a fan of his pessimistic and sarcastic personality. He was constantly complaining about the people and small-town setting of Stars Hollow, despite everyone’s best efforts to welcome him into their town. For this reason, he was generally disliked by the town members. However, as I think back on it, his attitude may have been justified considering his tumultuous relationship with his family.

Jess first ran into Rory at a welcome party that Lorelai hosted just for him, and their natural interest in each other sparked immediately. Although he continued to treat her with sarcasm and a certain coolness, he did so in a playful manner. Jess was indifferent toward the rest of the town, but he clearly invested a special attention in Rory. When he stole her book, for example, it was an opportunity for him to add his own annotations and insights before returning it to her, proving his interest in reading as well as his adoration toward her. 

The Jess-haters out there often complain that he was the “bad-boy” who constantly stirred up trouble and negatively influenced Rory, but I would disagree. To be fair, Jess was no angel, and there were definitely occasions where he caused trouble in the town; he skipped school to work extra hours at Walmart, got involved in school fights, and crashed Rory’s car while they were recklessly driving at night. These were certainly neither the brightest nor safest ideas, but he never had malicious intentions toward Rory. On the contrary, Jess always treated Rory with a particular, gentle affection that differed from his cold attitude toward others. While he ignored the guidance of Lorelai and his uncle Luke, he listened to Rory and allowed her to change his mind. As the series progressed, he gradually made his way into Rory’s life, always ready to help Rory in difficult situations. From fixing a broken sprinkler to supporting Rory in her aspirations, Jess was constantly by her side and ready to assist her. 

His lighthearted nature also made him easier to get along with, which clearly attracted Rory from the beginning. The two kept inside jokes with each other and shared a love for reading and music, allowing them to connect on a deeper level. Because of their shared interests, they were able to have intimate and interesting conversations that went beyond the surface-level chats between Rory and Dean. 

However, Jess was not free from his faults, and his tendency to shut out the world during difficult times often hurt his relationship with Rory. Due to his complicated and unstable childhood, he grew up with trust issues and a fear that everything was temporary. Especially during the earlier stages of his stay in Stars Hollow, Jess defied his authority figures and pushed away those who were simply trying to help him. At the height of their relationship, Jess left Stars Hollow and moved to California without leaving a single note for Rory. In several other instances, Jess revealed his inability to communicate with Rory, bailing when things got hard. At the same time, I do not blame him for his decisions. He was trapped in a difficult period of life, having been denied the opportunity to graduate and having no place to call home. Ultimately, it wasn’t because Jess didn’t want people to like him, but because he did not know how to let down his boundaries and reveal the thoughtful nature underneath. 

What was admirable about Jess’ character was his willingness to change. Unlike Rory’s other boyfriends, who exhibited generally the same behavior throughout all of the seasons, Jess experienced a character development that made him deserving of Rory’s love. After living with his dad in California, he returned to Stars Hollow with a successful publication and a collaboration with a publishing company in Philadelphia. During his absence, Rory’s life had fallen into shambles–she dropped out of Yale, was living with her grandparents, and had no plans for her future. With a changed perspective on life and a newfound maturity, Jess saw through Rory’s negligence. He was the one who reminded her with his famous line, “Why did you drop out of Yale?”, that none of her decisions aligned with who she was inside and that he knew she could do better. From the trouble-making teenager he once was, Jess grew into a successful man, yet his love for Rory remained unchanged. Again and again, he was able to prove how much he cared about her and wanted her to reach her full potential

Although Jess was introduced into the show as an unreliable, reckless teenager, he was able to prove to both Rory and the audience that he was able to change. He loved Rory unconditionally and was constantly by her side and pushing her to realize her true potential, even if it meant giving her some tough love.

Boyfriend #3: Logan Huntzberger

When it comes to Logan Huntzberger, my feelings are incredibly mixed. Logan was the last of Rory’s three main boyfriends, appearing during the later seasons of the show. At this point, Rory was attending Yale and had already matured into an aspiring journalist. Logan, the wealthy and adventurous college boyfriend, often gets credit for helping Rory step out of her comfort zone. Despite their passionate connection, however, Logan was not Rory’s best match in my opinion. 

Logan came from a privileged background, with a family steeped in wealth and connections that opened doors he didn’t even realize were closed for others. His upbringing gave him a rather ignorant mindset, and though he loved Rory, his perspective was limited. He never truly understood the sacrifices Rory and her mother made. His reckless behavior, which often involved his family’s fortune, revealed an insensitivity to the realities that Rory knew so well, having been raised by a single mother. Logan used his money as a means of spoiling Rory and keeping their relationship thrilling, but much of it felt like a superficial escapism rather than a partnership rooted in shared growth. While their adventures and extravagant trips were fun, they created barriers that kept their real-world problems away. Rory’s academic challenges, her identity crisis at Yale, and her temporary separation from her mother were often soothed by Logan’s wealth and distractions. In Logan’s world, consequences seemed optional, and it was never a place where Rory could grow and face her difficulties head-on. 

Because of his incredible fortune, Logan had a false sense of security, which seemed to rub off on Rory the longer they stayed together. Logan always had a carefree approach to his life, which he displayed proudly through his participation in the Life and Death Brigade, an elite secret society at Yale, and his party lifestyle. He thought little of the impacts his decisions would have on his life because he relied heavily on his family’s financial security to rescue him. Even while attending Yale, he would attend parties daily and neglect his academics, which quickly affected Rory’s lifestyle. Rory, who used to be defined by her independence and determination, soon fell behind in her studies. When she chose to drop out of Yale, Logan didn’t bat an eye. In fact, it was because they got arrested for stealing a yacht that Rory finally broke under the pressure. At its core, Rory and Logan’s relationship became increasingly codependent, and his chaotic world had a negative impact on her growth. A strong partnership should encourage individual development, not encourage one person to take irrational risks for the sake of the other. 

Logan Huntzberger was an exciting chapter in Rory’s life. He opened her up to new experiences, and their chemistry was undeniable. However, he was more of a catalyst for her personal exploration than a life partner who complemented her values and ambitions.

Conclusions

In the end, Rory did not end up with any of her old boyfriends, and for good reasons. Dean, Jess, and Logan all played a significant role in her growth, but none of them were ideal long-term partners. Dean was her first love, but his emotional immaturity and haughtiness clashed with Rory’s ambitious dreams. Jess challenged Rory intellectually, yet his emotional unavailability and self-destructive tendencies made him unreliable. Logan, while exciting and supportive at times, brought a world of privilege that distanced Rory from her core values and sense of independence.

Ultimately, Rory shouldn’t have chosen any of them because they all represented phases of her life, not partners who could support her as she truly discovered her own path. She needed to find someone who shared her vision for the future, valued her independence, and could grow alongside her—qualities none of these three consistently provided.

Sources

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Gresge, Gabrielle. “The Life And Death Brigade From “Gilmore Girls” Is Real.” Brit + Co, 27 November 2023, https://www.brit.co/real-life-and-death-brigade/. Accessed 13 October 2024.

Kaufman, Ruby. “Dean Forester, Gilmore Girl’s Worst Character.” The Elliot Magazine, 2021. The Elliot Magazine, https://elliottmag.com/all-posts/2021/10/dean-forester-gilmore-girls-worst-character. Accessed 12 October 2024.

Martinez, Kelly. “Dean Forester was NOT a Bad Guy, Here’s Why.” Medium, 11 October 2022, https://medium.com/@lina.writes/dean-forester-my-defense-part-1-cf5a851c3489. Accessed 12 October 2024.

Peel, Yamile. “Essay: A Character’s Fall from Grace and Those Who Choose to Emulate.” The UCSD Guardian, 16 April 2023, https://ucsdguardian.org/2023/04/16/essay-a-characters-fall-from-grace-and-those-who-choose-to-emulate/. Accessed 12 October 2024.

Tiwari, Shreya. “The cultural relevance of Gilmore Girls.” The Johns Hopkins News-Letter, 9 November 2023, https://www.jhunewsletter.com/article/2023/11/the-cultural-relevance-of-gilmore-girls. Accessed 12 October 2024.