Storylines
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. To pay tuition, Lorelai asks for money from her estranged wealthy parents, Richard and Emily. They agree to pay for Rory's education on the condition that the two come to their house every Friday night for dinner. Before leaving Stars Hollow High School, Rory meets Dean Forester (Jared Padalecki). Rory almost convinced herself not to go to Chilton because she did not want to leave Dean, but after learning of her mother's huge sacrifices, she decided to go to Chilton. Rory and Dean date for two seasons, only breaking up once when Dean told Rory he loved her on their 3-month anniversary, and she replied that she would have to think about it, but they eventually reconcile. 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. While at Chilton, Rory becomes engaged in a feud with a close academic rival, Paris Geller. Though the two later become friends, the rivalry continues into their university studies. Rory reluctantly agrees to run as Paris's vice president for student government and wins. She also writes for the Chilton paper, The Franklin. Rory and Paris join the "Puffs", a secret sorority at Chilton.
When she meets Jess Mariano (Milo Ventimiglia), Rory begins to fall in love with him. They become friends first but start to date after Dean breaks up with Rory because he sees that Rory likes Jess. However, various problems make their relationship difficult. After Jess skips school to go to work at Walmart, causing him to be unable to graduate or to take Rory to Prom, Jess decides to leave to go to California to see his estranged father, effectively breaking up with Rory. Jess does not tell Rory he is leaving but later calls and does not say anything on the phone until Rory catches on that it is him and reveals that she might have loved him but would just have to get over it. Later that year, still upset, Jess returns and tells Rory that he loves her and then leaves again.
After graduating from Chilton as valedictorian and with a 4.2 GPA, Rory goes on to attend Yale University, her grandfather's alma mater, in season four—although her entire life she had wanted to go to Harvard—having decided that the benefits of Yale outweighed her dream of studying at Harvard. During her first year, Rory resides at Durfee Hall and shares a dorm room with Tana, Janet, and fellow Chilton alumna Paris Geller. She moves to Branford College, the same residential college that her grandfather, Richard Gilmore, lived in, [1] at the beginning of her sophomore year. There, she shares a dorm room with Paris. 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. She writes for the Yale Daily News and is its editor toward the end of her studies.
While at Yale, Rory reconnects with Dean, who married Lindsay (a fellow schoolmate from Stars Hollow High) straight after high school, but it is soon clear that he impulsively did it as a rebound from Rory. During the same period, Jess shows up unexpectedly at Yale to see Rory and asks her to run away with him, but she refuses. Dean gets jealous, but he and Rory grow closer and have an affair, during which Rory loses her virginity. Lorelai is angry and disappointed in Rory, who decides to leave for Europe with her grandmother for the summer to avoid conflicts. Shortly after, Dean separates from Lindsay, and they continue to see each other. 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.
Meanwhile, Rory makes the acquaintance of the heir to the Huntzberger Publishing Company, Logan Huntzberger (Matt Czuchry), who invites her to join a Yale secret society called the Life and Death Brigade. She soon becomes interested in him, and after Dean breaks up with her (she was detained at a party arranged by her grandparents to introduce her to the wealthy and eligible sons of their Yale alum friends, including Logan), she makes the first move at her grandparents' vow renewal. Their relationship begins casually as a "no strings attached" affair because Logan makes it clear that he does not want to commit to a relationship.
However, as time passes, Rory grows dissatisfied with their open relationship, and after a day of drunken introspection, she suggests they should end their sexual relationship and be friends because she is "a girlfriend kind of girl." Logan interprets this as an ultimatum and unexpectedly agrees to date her exclusively. 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. Logan affirms his commitment to their relationship, but the pressure exerted by the Huntzbergers continues to dog the couple.
To make amends, Logan's father, Mitchum Huntzberger, gives Rory an internship at one of his newspapers, the Stamford Eagle Gazette. At the end of her internship, Mitchum tells Rory she does not have what it takes to be a journalist, but she would make a good assistant. 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. Rory and Lorelai barely speak for months and are only reconciled mid-season six, in "The Prodigal Daughter Returns."
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. He has achieved something with his own life by writing a novel, and he encourages her to see that her current choices do not suit who she really is. 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 doggedly pursues her former editor for a job at the Stamford Eagle Gazette, takes on extra courses at Yale to make up for her time away, and is unexpectedly elected editor of the Yale Daily News, taking over from Paris.
Rory and Logan reunite and cement their relationship despite his post-graduation spell working in London, England, and a failed business. She cultivates new friendships with Olivia and Lucy, girls involved in the arts and drama, but these relationships become fraught when Marty, a friend who had a crush on Rory in an earlier season, is revealed to be Lucy’s boyfriend. Having been unexpectedly elected editor of the Yale Daily News, Rory’s tenure later ends and leaves her feeling deflated. She continues to work towards her goal, applying for the Reston Fellowship and becoming an intern at The New York Times , as well as applying and interviewing for other jobs. She turns down one firm job offer, counting on getting the Reston Fellowship. 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.
At Rory’s own graduation party, where it is revealed she graduated with honors and membership in Phi Beta Kappa, [2] Logan unexpectedly proposes marriage and asks her to move to Palo Alto, California, with him. She considers his offer but ultimately declines, suggesting they try to maintain a long-distance relationship. She says that she relishes the openness of her life and the opportunities before her; marriage now would limit that. Logan, however, finds the prospect of "going backwards" in their relationship unappealing and issues the ultimatum that it is "all or nothing." Rory wordlessly returns his engagement ring, and Logan walks away. As of the final episode, Rory had prepared numerous résumés to mail before going on vacation with her mother. When another reporter drops out at the last moment, she is offered a job as a reporter for an online magazine, covering Barack Obama's first presidential campaign and his bid for the Democratic Party nomination. Luke throws Rory a surprise graduation party, closing the original series.
Nine years later, Rory is in a rut. 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. She has been dating a man named Paul for two years but does not seem to be invested in their relationship. After breaking up with Paul, she also engages in casual sex, including with a nameless man in a Wookie costume.
While jetting back and forth between America and London, Rory sees Logan on the side. He, in turn, cheats on his fiancée with Rory but will not leave her for Rory. Rory interviews for many more jobs, but she does not receive any promising offers. Rory ends up back in Stars Hollow and becomes the editor of the Stars Hollow Gazette. 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.
Rory and her mother have a falling out when Rory tells Lorelai about the book, as Lorelai does not want her life written about. Rory continues to wander, but she is very determined to write her novel. She breaks things off with Logan for good, believing their relationship is not what is best for her. She ends up reconciling with her mother and is present when Lorelai marries Luke. Rory later reveals to Lorelai that she is pregnant. While the father's identity is not explicitly stated, the timing implies that it is Logan's child.
