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Rory Leigh Gilmore (Alexis Bledel) is the daughter Lorelai Gilmore (Lauren Graham) and Christopher Hayden ( David Sutcliffe) born on October 8, 1984 at 4:03 a.m.. Rory and her mom are alike in almost every way. They both consume and eat a wide variety of junk food, have a strong obsession with coffee, especially from Luke's Diner, old time classic movies, and all types of music from the 70s and 80s. Both are known to make witty, fast, cultural references at the drop of a hat. Although not as wild as her role model of a mother, Rory knows how to have fun. After Lorelai gave birth to Rory, she ran away from her parents, Emily and Richard, to the small town of Stars Hallow, Conneticut. There, she got a job as a maid at the Independence Inn, which she would later become manager of. Lorelai and Rory lived in a small shack behind the inn. Eventually, Lorelai bought a house in Stars Hallow when Rory was 11 years old.
Rory grows up exhibiting an extreme amount of intelligence. From the moment that she was able to speak, she dreamed of going to the prestigious Harvard University. When is in her sophomore year of Stars Hallow High, she gets news that she has been excepted to Chilton Preparatory. Tuition for Chilton is out of this world, and Lorelai knows that she cannot afford it. She has no other choice but to ask her rich estranged parent for money. Lorelai goes to there house and tells them the news of Rory enrollment. Emily and Richard are thrilled. They hint about the tution fees, and Lorelai pops the question to them. They accept, but on one condition. The Gilmores must meet weekly for Friday night dinners.
Except on one occasion in the first season, 'Christopher Returns' Rory has no contact with her paternal grandparents, Straub and Francine Hayden. At a Friday night dinner with the Gilmores at which Rory is present, Straub states that Lorelai's pregnancy ruined Christopher's future. Emily later reassures Rory that her birth is not a disappointment to them.
Before leaving Stars Hollow High School, Rory met fellow schoolmate Dean Forester, who became her first steady boyfriend. Rory and Dean date during two and a half seasons before Dean ends the relationship, alleging she has been attracted to Jess Mariano, the nephew of Luke Danes, since he first arrived in Stars Hollow. As it turns out, he is absolutely correct, as Rory and Jess have a magnetic connection to each other. Rory and Jess date in season three, but trust and communication issues plague the relationship, and it ends when Jess departs for California shortly before Rory graduates from Chilton. Rory contends with Lorelai’s suspicion of her boyfriends; though her mother comes to accept Dean, Lorelai never warms to Jess. As part of the series' depiction of her coming of age, Rory attends her first formal dance with Dean, makes her society debut with him, and, after a false-start, reciprocates his “I love you.” In her relationship with Jess, Rory is shown for the first time to be considering losing her virginity.
During her time at Chilton, Rory becomes engaged in a feud with close academic rival, Paris Gellar. Though the two later become friends, their relationship remains characterized by a rivalry which continues into their university studies. At Chilton, Rory must often decide to what degree she will seek to fit in socially, as well as being subject to the strain of constant pressure to achieve academically. She receives her first bad grade, misses an important test and is reprimanded, first for being anti-social, and later, for joining Chilton’s secret sorority, The Puffs. Rory achieves much academic success, but anxiously studies for finals and SATs, and applies to Ivy League Universities, Harvard, Princeton and Yale. She also reluctantly runs for student government with Paris and wins, and writes for the Chilton paper, The Franklin.
After graduating from Chilton as valedictorian, Rory attends Yale University in season four, having decided that the benefits of Yale outweighed her dream of studying at Harvard in season three. Rory resides in Branford College, the same residential college of her grandfather, Richard Gilmore. Rory majors in Journalism and pursues her interest in it; 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 towards the end of her studies.
During her first year at Yale, Rory has only one date, although Jess returns unexpectedly and tells her he loves her. He leaves before she can make any response. Rory also turns to Dean for support when she is stunned to be failing a class at Yale, and later, when she needs to be driven home from a bar after completing her finals for the year. The same night, Jess returns again, interrupting Dean and Rory at her dorm, just as Rory is confronting Dean about his marriage and their intimate friendship. Jess asks Rory to begin their relationship anew, away from Stars Hollow and Yale, and live with him in New York. Upset and confused after a tumultuous year and a burgeoning rapport with Dean, Rory declines and Jess leaves. Confiding in Lane soon after, Rory says she appreciates the dependability of Dean, reflecting that Jess was attractive in a number of ways, but that she no longer finds his unreliable and unpredictable nature appealing.
In the season four finale, Rory rekindles her relationship with Dean and loses her virginity to him. This choice is the subject of an intense fight between Rory and Lorelai, chiefly because Dean is married to Lindsay at the time. Rory leaves for Europe with her grandmother and barely communicates with Lorelai. Dean separates from Lindsay and the pair date during Rory's sophomore year in season five, though obstacles make the period difficult. Dean ends the relationship when Rory is late to meet him: she is detained at a party arranged by her grandparents to introduce her to the wealthy and eligible sons of their Yale alumni friends.
One of these bachelors, Logan Huntzberger, heir to the Huntzberger newspaper-publishing empire, had already begun to interest Rory before her relationship with Dean ended. She accompanied him to a woodland meeting of a secret society at Yale, The Life and Death Brigade, in order to prepare an article for the Yale Daily News. After waiting for him to ask her out, Rory decides to approach him at her grandparents’ vow-renewal. Their relationship begins casually as a "no strings attached" affair because Logan makes it clear he is averse to commitment in 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. At her first time to dinner at Logan’s family home, the Huntzbergers reject Rory as a fit girlfriend for their son because of her aspirations to work and her background. However, Logan affirms his commitment to their relationship, although the pressure exerted by the Huntzbergers continues to dog the couple.
At least partly as a conciliatory gesture, Logan’s father, Mitchum Huntzberger, who was not present at the dinner, offers Rory an internship at one of his newspapers, the Stamford Eagle Gazette. Rory accepts and after some initial difficulties, she looks forward to an assessment of her performance by Mitchum. To Rory’s chagrin, Mitchum informs her that she does not have what it takes to be a journalist, although she would make a good assistant. Upset and angry, Rory, cajoles Logan away from his sister’s engagement party, held 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 in to her grandparents’ pool house, and works at Emily’s branch of the Daughters of the American Revolution. Rory and Lorelai barely speak for months and are only reconciled mid-season six, in ‘The Prodigal Daughter Returns’.
Experiencing some problems with restricted liberty living with her grandparents, chiefly centering on her sexual relationship with Logan, Rory reassesses her life after another unexpected visit from Jess, who has achieved something with his own life by writing a novel and who encourages her to see that her current choices do not suit who she really is. However, Jess’s visit and Rory’s realisation about her lifestyle 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.
Logan woos Rory back, but when she discovers he has slept with some of his sister’s bridesmaids during their time apart, she feels betrayed and their relationship experiences some difficulties as a result. This period of awkwardness coincides with an invitation to see Jess at an open house held at his place of work, Truncheon Books, Philadelphia. Jess and Rory’s visit ends with an aborted kiss between the ex-lovers, and Rory dispels Jess’s assumption that she is single by affirming her love for Logan despite their problems.
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 girls involved in the arts and drama, Olivia and Lucy, although 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 comes to an end and leaves her feeling deflated. She continues to work towards her goal, applying for the Reston Fellowship, to become 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 held at her grandparents' home, 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.
In the series finale, Rory prepares hundreds of resumes to mail to prospective employers just before she and Lorelai are to embark on a summer-long vacation visiting roller coasters throughout the United States. During a networking meeting with the editor of an on-line magazine for which she had previously written articles, Rory is offered the opportunity to become a reporter for that magazine and to travel with other journalists covering Barack Obama's presidential campaign and his bid for the Democratic Party nomination, when another reporter drops out at the last moment. She accepts and faces the challenge of entering the world of work and leaving her mother behind in Stars Hollow.