Lorelai 'Rory' Leigh GilmoreRory Leigh Gilmore, played by Alexis Bledel, is the only child of Lorelai Gilmore and the first-born daughter of Christopher Hayden, born on October 8, 1984 at 4:03 a.m. Rory shares her mother's taste in junk food, coffee, movies, music, and much more. They both exhibit a talent for witty, fast-paced, pop-culture-laden dialogue, and they are extremely close. Rory spent her childhood in the Independence Inn in Stars Hollow where her mother originally worked as maid. Lorelai was later able to buy a house, where Rory spent her adolescent years.
The series pilot indicates that Rory harbours a long-held dream to study at Harvard University, and it is for this reason she transfers from Stars Hollow public high school to the prestigious Chilton Preparatory. She attends Chilton for her sophomore, junior and senior years of high school. Lorelai is forced to ask her parents for help to pay Chilton's tuition fees, ending their relative-estrangement since Rory's birth. Rory grows close to Emily and Richard, especially her grandfather, although she also comes into conflict with them periodically during the series. The developing relationship between grandparents and granddaughter is also a source of contention between Rory and Lorelai.
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. 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 characterised 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 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 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.
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