The Ultimate Ranking of Rory's Boyfriends in Gilmore Girls

Summary

The hit show

Gilmore Girls

explores Rory Gilmore's love life with four different boyfriends, sparking debates among fans on who she should have ended up with.

Paul, an insignificant boyfriend introduced during the revival, served no purpose in advancing Rory's character development or the overall plot.

Jess Mariano, on the other hand, stands out as Rory's top boyfriend due to their profound understanding and respectful relationship, even after their breakup.

The hit television show Gilmore Girls, which aired in the early 2000s, captured the charm of small-town life and showcased Rory Gilmore's tumultuous love life. Throughout the series, Rory had four different boyfriends, and the show predominantly revolves around the relationships of Rory and her mother, Lorelai. Romantic interests play a significant role from the start, and Rory's love life becomes a topic of debate among fans regarding which character she should have ended up with. From Dean Forrester, her first on-screen boyfriend, to Logan Huntzberger, one of her most serious relationships during her time at Yale, and even her forgettable boyfriend Paul during the revival, Rory's romantic history is diverse. Jess Mariano also remains a constant figure in Rory's life throughout the original series and revival. While opinions on Rory's best boyfriend may vary among fans, some are clearly more favored than others.

4 Paul

Portrayed by Jack Carpenter, Paul enters the Gilmores' world in Gilmore Girls: A Year in the Life only to be quickly forgotten. Initially introduced as Rory's long-term boyfriend, Paul fails to make any lasting impact on anyone, including Rory herself. It appears that his sole purpose is to further Rory's storyline, as his lack of a last name symbolizes his role as a mere plot device. With his conservative persona, Paul's presence starkly contrasts with Rory's past relationships, which were both exhilarating and somewhat unhealthy. This fundamental disparity ultimately leads to Rory's lack of interest in him.

Despite being Rory's longest relationship, Paul is given very little screen time, which relegates him to the bottom of her list of romantic interests. Although he is a genuinely decent person, the writers missed an opportunity to showcase Rory's personal growth through this storyline. Paul fulfills his role effectively by laying the groundwork for Rory's infidelity and providing a means for her past boyfriends to resurface in the Netflix revival. It is unfortunate that Paul is treated so negligibly, but his forgettable presence does offer some comedic relief in Gilmore Girls: A Year in the Life.

3 Dean Forester

Dean Forester, played by Jared Padalecki, is Rory's first boyfriend in Gilmore Girls. The two meet in the pilot episode and initially experience a sweet and innocent young love. However, their relationship takes a turn when Jess Mariano enters the picture, leading to a rapid deterioration in their connection. By season 3, Dean and Rory have broken up, and their final explosive argument highlights the toxicity of their relationship. In season 4, Dean gets married but continues to struggle with his feelings for Rory, eventually succumbing to temptation and cheating on his wife.

Despite its flaws, Rory and Dean's relationship embodies the comforting familiarity of young love. Dean genuinely cares for Rory, even though he may not always express it effectively. He often plays the role of the clueless lover, making mistakes both for and with Rory in the name of love, which suits his character well. He handles the ups and downs of their relationship with grace and seemingly finds happiness in Gilmore Girls: A Year in the Life. Ultimately, Dean's immaturity prevents him from rising on Rory's list of boyfriends, but his sincerity still makes him a compelling choice.

2 Logan Huntzberger

Rory encounters Logan Huntzberger during her time at Yale, where they both work for the Yale Daily News. Their romantic connection begins just as Rory's relationship with Dean ends, with Logan offering comfort after the breakup. Their relationship progresses gradually, with both of them impressing each other through creative gestures. Despite Logan's parents' disapproval, he treats Rory with respect and appreciates her values, though his snobbish nature occasionally emerges in his words and actions.

Despite his flaws, Logan brings out a side of Rory that her previous boyfriends have not. With him, she takes more risks, which have both positive and negative outcomes. In A Year in the Life, it is evident that Rory and Logan still harbor feelings for one another as she cheats on her boyfriend Paul with Logan and later becomes pregnant. Their relationship is filled with love and understanding, but sometimes lacks the necessary maturity to thrive in adult life while still in college.

1 Jess Mariano

Luke's nephew, Jess Mariano (Milo Ventimiglia), makes his first appearance in Stars Hollow during the second season of Gilmore Girls, causing a disruption in Rory and Dean's relationship. From the very beginning, there is a palpable chemistry between Rory and Jess, as audiences witness a softer side of the initially standoffish Jess during their interactions. These two characters share a deep understanding and bond over their mutual love for literature. Jess opens Rory's eyes to what she has been missing with Dean. Their connection is undeniable, with Jess' rebellious nature balancing out Rory's more reserved demeanor.

Rory and Jess' relationship is founded on respect and a shared understanding of what love means to them, and this connection continues to thrive as the series progresses. Despite the ups and downs they face, each time they reunite, it is evident that they care deeply for one another. Unlike Rory's other boyfriends, their relationship is able to withstand the challenges they encounter, and it becomes a consistent source of love and support beyond just a romantic connection. Even years after the events of the original Gilmore Girls, their ability to love and respect one another is why Jess holds the top spot as Rory's number one boyfriend.