Rory dreams of studying at Harvard University and gets accepted into the prestigious and fictional Chilton Academy, where she stays for her sophomore, junior, and senior years of high school.

Dean escorts Rory when she is presented to society at a debutante ball hosted by her grandmother's chapter of the Daughters of the American Revolution.

During her first year, Rory resides at Durfee Hall and shares a dorm room with Tana, Janet, and fellow Chilton alumna Paris Geller.

At Yale, Rory majors in English and pursues her interest in journalism; she wants to be a foreign correspondent, and her role model is Christiane Amanpour.

Lorelai is angry and disappointed in Rory, who decides to leave for Europe with her grandmother for the summer to avoid conflicts.

They break up after Dean arrives at the Gilmore mansion to see that Rory—wearing a family diamond tiara, earrings, and necklace—is having a coming out party attended by male students from Yale.

On her first time to dinner at Logan’s family home, the Huntzbergers reject Rory as a fit girlfriend for their son because she aspires to work and because of her background.

To make amends, Logan's father, Mitchum Huntzberger, gives Rory an internship at one of his newspapers, the Stamford Eagle Gazette.

Upset and angry, Rory cajoles Logan into leaving his sister’s engagement party at a marina to steal a yacht and vent her frustration.

When apprehended, Rory is sentenced to 300 hours of community service and rethinks her lifelong ambitions and current path at Yale.

Her decision to take time off to consider her options precipitates the most sustained rift with Lorelai to date, beginning in the season five finale.

She moves into her grandparents' pool house, joins Emily’s branch of the Daughters of the American Revolution, and begins working for the organization.

Experiencing some problems with the restricted liberty of living with her grandparents, chiefly centering on her sexual relationship with Logan, Rory reassesses her life after another unexpected visit from Jess.

However, Jess’s visit and Rory’s subsequent realization that she is doing nothing with her life precipitate an argument with Logan, and the couple are estranged for some time.

Rory and Logan reunite and cement their relationship despite his post-graduation spell working in London, England, and a failed business.

Having been unexpectedly elected editor of the Yale Daily News, Rory’s tenure later ends and leaves her feeling deflated.

When she is rejected, Rory is in turmoil, unable to concentrate on a final exam about John Milton’s epic poem, Paradise Lost, and generally experiencing great uncertainty about her future.

She has become a successful freelance journalist but was fired from a job to ghostwrite a book and gave up her apartment to stay in different places like New York, London, and Stars Hollow.

While at work one day, Jess visits her and gives her the idea of writing a book about her life and relationship with her mother, Lorelai.

Amy had in mind a girl with real complexity—a kid who was fiercely independent and intellectually precocious but naïve in matters of the heart.

"[3] Margaret Lyons of Vulture.com wrote "Rory's worst attribute, other than her slouchy posture, is her lack of impulse control.

"[9] After watching the pilot of the series, Ron Wertheimer of The New York Times wrote: "Ms. Bledel, new to television, creates an appealing blend of precocious wisdom and teenage anxiety.

"[10] Variety critic Laura Fries called Bledel "the real star" for her ability "to articulate the wide range of often subtle emotions that confront teenagers.

"[11] In his article discussing child actors playing "more meaningful characters", Allan Johnson of the Chicago Tribune cited Bledel as one of "two more young people who are showing some depth in their various portrayals".

[12] Shirly Li of The Atlantic praised the friendship between Rory and Paris, describing it as "a deep platonic female relationship that didn't come prepackaged, but instead developed in front of viewers' eyes.

Her affair with married ex-boyfriend Dean Forester and her cruel body-shaming remarks, such as the “Die, Jerk” incident, illustrate her moral lapses and growing entitlement.

The shift in Rory's character, particularly during her college years at Yale, highlights a departure from the diligent, relatable girl-next-door to a more flawed and less likable individual, sparking ongoing debate among fans about her journey and development throughout the series.