From the very first moments of Rory’s A Year in the Life story.

Her sudden reluctance to embrace the long-awaited opportunity of Chilton, driven by a fleeting connection, established a pattern of hesitation and rationalization that would echo throughout the series. This early instance foreshadowed Rory's later difficulties in fully embracing academic pursuits, career paths, and even romantic relationships, mirroring her mother’s tendency to sabotage or resist deep involvement in Lorelai’s dating history in Gilmore Girls. The pilot episode serves as a crucial early warning of an Achilles heel that would shape Rory's journey, much like it defined Lorelai's.

It Was Obvious Rory Had Lorelai's Commitment Issues From Gilmore Girls' Pilot Episode

Rory Flip-Flops On The Topic Of Chilton As Soon As She Meets Dean

Sometimes, pilot episodes do not do a great job of reflecting how characters’ traits unfold throughout the series, but the writing of Gilmore Girls’ pilot is really strong. Right away, Rory is established as somebody who runs away from big opportunities rather than taking the reins in her life at the right time. As established in the diner conversation, until this point, Rory has been excited about Chilton, so suddenly deciding she wants to stay at Stars Hollow High understandably feels like a curveball to Lorelai, and she intuitively suspects there is a boy in the picture.

While this is not a romantic issue at this point in the plot, it establishes that Rory has trouble committing to big life changes. It is also important that during the dinner conversation, Rory rationalizes her hesitation about Chilton by making it about Lorelai’s finances and her own goal to establish her own inn with Sookie.

Rory tends to act rashly and then rationalize her decision later - viewers see her do this again in the affair plotline in season 4. She rationalizes the decision by naïvely taking Dean’s assertion that his marriage is “over” at face value and arguing this point to a horrified Lorelai, while also claiming Dean’s was hers first. These mental gymnastics to justify her own behavior are a running theme. While it has made Rory an unsympathetic character to many, the reason Gilmore Girls is so well written is that Rory’s background arguably makes this behavior less surprising and, narratively, more interesting.

Rory's Problems With Commitment Continue Throughout Gilmore Girls

Rory’s Commitment Issues Extend To College And Relationships

Despite being continually told she is “special” as she grows up, Rory does not seem to have a genuine and healthy self-esteem. While the pilot establishes that Rory is smart and has an unwavering focus on reading, this and her family’s reinforcement of her brilliance do not prepare her for the distress of unforeseen challenges to that narrative. One event where viewers see this come into play is her struggle to adjust at Chilton, not being the smartest in her class anymore.

Rory is without her mother's grounding influence at college...

While Rory ultimately proved Heaster Charleston wrong, she struggles at first at Chilton, which is based on a real-life school in Gilmore Girls. Her distress at not being able to retake the English test she was late for is understandable in her particular circumstances, and, with Lorelai’s help, she can make up the grade in future projects. This highlights the importance of Lorelai’s immediate , while Rory is without her mother's grounding influence at college. She drops out of Yale - when she does it, she intends the drop-out to be permanent, which is a drastic departure from her well-established goals.

Viewers also see this flaw play out in Rory’s romantic life. Romantically, this is more of an inability to let go of her past connections, leading to two-timing and stringing love interests along. Some of it echoes Lorelai’s mistakes, such as deciphering gratitude from love. This is a major issue in Lorelai and Max’s relationship, and it plays out between Rory and Dean. Lorelai also reinforces the idea of how good Dean is toward Rory, making it more difficult to let go despite his overbearing characteristics.

A Year In The Life Fixes This Flaw For Lorelai, But It Leaves Rory In The Same Spot

Rory’s Circumstances Are Difficult In The Gilmore Girls Revival

In A Year in the Life, Lorelai addresses the harsh reality of her long-standing fear of commitment, a pattern of self-sabotage rooted in anxieties about rejection stemming from her upbringing. Facing her own mortality after her father's death, she realizes the security and value of her relationship with Luke outweigh the perceived risks of commitment. This marks a significant step in her emotional growth, moving beyond the avoidance that characterized her past relationships in the original series. This is such a satisfying growth, as Lorelai had minimal relationship experience before having Rory, and Chris’ flightiness clearly affected her outlook deeply.

Rory has not healed her attitude to commitment. Something that is refreshing about Gilmore Girls’ writing is that Rory has many flaws, and she doesn’t necessarily have everything figured out in the Gilmore Girls revival that undoes Rory’s development, despite her privileges. This may irritate some, but it arguably makes her more relatable. In A Year in the Life, Rory is perhaps the most depressed she has ever been. She has lost her beloved grandfather, her career opportunities are diminishing, and she feels lost. Her lack of control over her life potentially contributes to her ongoing affair with Logan.

If Gilmore Girls Season 9 Ever Happens, It Could Finally Address Rory's Biggest Problems

Rory’s Book Could Be The Key To Processing Her Challenges

A Year in the Life ended with Rory’s pregnancy announcement, which reinforces that Gilmore Girls is ultimately a story about a mother and a daughter, bringing it full circle. If there is a season 9, it would be wonderful to have Rory really break the cycle and challenge the history-repeating-itself structure of the show. After all, Rory has decided to write a book about her life and upbringing - unless she is planning on putting the onus on everybody else, it would make sense for her to dig deep and address her own issues for the book.

The process of writing could force her to reflect on her own choices...

Rory's book could serve as a catalyst for her to finally step into her own narrative, rather than remaining entangled in the stories of those around her. Instead of solely focusing on her mother's life or her past relationships, the book could become Rory's vehicle for self-discovery and asserting her own identity. The process of writing could force her to reflect on her own choices, confront her career disappointments, and articulate her personal aspirations.

Gilmore Girls season 9 could perhaps see Rory initially using the book as a way to process her life through the lens of her mother's experiences, as the initial conflict with Lorelai suggests. However, as the season progresses, Rory might realize the limitations of this approach. To truly create meaningful work and move forward, she would need to shift the focus inward, grappling with her own vulnerabilities, ambitions, and the consequences of her decisions.