- ‶But... I've always done what was asked of me″
- —Rory to Mitchum Huntzberger[src]
Lorelai "Rory" Leigh Gilmore is the only daughter of Lorelai Gilmore and the first born daughter of Christopher Hayden (notably her parents were 16 years old when Rory was born). She was born on October 8th, 1984 at 4:03 in the morning. Though born in Hartford, Connecticut, Rory was raised in Stars Hollow where her mother originally worked as a maid at the Independence Inn. Rory had limited contact with her grandparents, Richard and Emily Gilmore, when she was growing up, usually only seeing them during the holidays.
It wasn't until she began school at Chilton that her grandparents became a regular presence in her life. Her father was rarely around during her childhood years. It is stated that Lorelai had wanted Rory to attend Harvard since she was three years old. At the start of the series, she is a sophomore in high school, and when the series concludes, she is a recent college graduate.
Rory is defined by her mother's decision to leave her parents and their wealthy life behind, as Emily, Richard and Lorelai herself, put the expectations of a "great future" (the one the three of them imagined for Lorelai) on Rory's shoulders. She's always applying herself scholastically and doing well when asked to perform tasks that have instructions (notably she tells Mitchum Huntzberger she's always done what was asked of her, and receives a higher SAT score in maths than in verbal).
Rory is an introverted, at times socially awkward person, who fares best in Stars Hollow, where she seems to feel comfortable being herself, as part of the town. For whatever reason, in spite of her nature being to plan and preferring to know what's coming ahead, Rory decides to become a journalist. While she is commended for her hard work as a writer, she falters completely in the world at journalism, somehow never realizing that maybe this is not the profession for her.
This could be attributed to the enormous expectations her grandparents and, inadvertently, her brilliant mother, have put on Rory, as well as Rory's biggest wish: to emulate her mother. This is substantiated by Rory's unwillingness to alter her predestined future, admit when something goes wrong or even accept that mistakes are good for her, instead feeling any "failure to comply with the prerequisites for her Gilmorian future" equal her being a failure as a person. Arguably, all Rory ever wanted was to live a comfortable, quiet life in Stars Hollow. She is often buried in a book or newspaper during her free time. She shares her mother’s tastes for junk food and movies, and also her quick wit— though Rory often relies more upon her book smarts (quite literally, as she often quotes the various novels she’s read) for her humor. She is generally friendly and sweet, and her wide blue eyes and rosy cheeks give her a youthful, innocent appearance.
Rory's story is mainly told through her studiousness, harnessed by her mother from an early age and by no means forced or rejected by Rory, but rather embraced as almost a sole identifying characteristic. She spends her first year of high school attending the local Stars Hollow High School with Lane, but is accepted to the prestigious Chilton which can improve her odds in getting accepted Harvard, a lifelong dream of Rory's. Shortly after starting her sophomore year, Rory starts attending Chilton leaving her best friend Lane Kim behind. During her last days at Stars Hollow High School, Rory meets the new kid in town and her first boyfriend, Dean Forester.
Rory attends the prestigious Chilton Prep for the rest of her high school career. To pay tuition, Lorelai asks her estranged parents for help and they agree to pay on one condition: Lorelai and Rory must attend a weekly "Friday Night Dinner" at 7:00 pm. Rory has a difficult start at the highly competitive Chilton, receiving her first ever D on a paper in Max Medina's English Literature class. After receiving the D, Rory spends hours studying for a Shakespeare exam for which she ends up being late, due to the fact that a deer hit her car, and was not allowed to take the exam. Max Medina eventually takes a special interest in Rory and after the incident, reaches out and tells her he has extra credit options that can help her make up for the missed test.
Rory begins to blossom at Chilton, and shows her potential to be a great and gifted student. She finishes her first year in the top 3% of her class. Notably, Rory's rocky beginning at Chilton is shadowed by a group of three girls, Paris Geller heading the trio. Paris and Rory continuously clash throughout their academic career at Chilton as Paris views Rory as competition – both for Harvard and early on, the affections of Paris' childhood crush, Tristin. Through some sort of twisted fate, the two tended to be paired in group projects and had a hot-and-cold friendship, eventually becoming more permanently positive. Upon graduation the two reflect on the major impact they've had on each other's high school experience. Notable classmates of Rory's at Chilton were Madeline, Louise, and Tristin (who had a crush on Rory until he was forced to attend military school). Rory had two boyfriends while she attends Chilton: Dean and Jess, but she is single when she graduates.
Rory is accepted to Harvard, Princeton, and Yale. Despite going through her whole life with Harvard as her dream school, Rory decides to attend Yale University where her grandfather was an alumnus. Her mother was initially against Yale, but after seeing Rory's interest in it, she warms to it and encourages Rory to attend. Rory is named Valedictorian and during her graduation ceremony, she delivers a tear-jerking speech that commemorates her grandparents and especially her mother's influence on her life. Her grandparents gift her a Toyota Prius for graduation, and Lorelai loves the idea of her daughter having a car because it will allow her to visit more often. Before departing the campus, Lorelai has Rory take a step back in the corridors, and let's her muse that the place isn't so scary anymore.
When Rory is denied financial aid for Yale, she approaches her grandparents without her mother's knowledge and asks them to pay for her college in the form of a loan. Richard agrees to pay for Yale as long as she waits five years after her graduation to start paying them back, with no interest. Rory accepts the condition, and she also reinstates their weekly Friday night dinners (which had ended when Lorelai paid back the money she owed her parents for Chilton). After returning from a summer trip backpacking in Europe, Rory realizes she wrote the orientation date down wrong. Instead of a week until orientation, she has to be at school in two days which means she and her mother have to scramble to prepare. With help from her mother and Luke, Rory moves into her dorm suite where she is quickly shocked to find Paris Geller as one of her suite-mates. During her first year at Yale as an English major, Rory gets back into a relationship with Dean, but she also creates new friendships, notably one with Marty (who secretly has feelings for Rory throughout their friendship).
Through Marty, Rory meets her future boyfriend Logan Huntzberger. Rory doesn't like Logan at first because of his seemingly privileged white male attitude and because of the way he treats Marty like a servant (as Marty had previously bartended for his parties). However, when Logan takes Rory to a memorable Life and Death Brigade event (which he is allowing her to cover for the Yale Daily News) they become friends. Some time later, Dean breaks up with Rory after she arrives to meet him late and tipsy with Logan and his buddies behind her. Logan comforts her. Rory begins to date Logan non-exclusively, but when she gets jealous of him being with other girls, Logan realizes he cares too much about her to lose her. He agrees to be exclusive with her which is a first for him. Rory attends a dinner with him at his parents' house, and despite his family's loud disapproval of her, they continue their relationship. Mitchum Huntzberger, Logan's father, apologizes for his family's behavior, and he offers her an internship at a local paper of which he owns. She accepts. Rory believes she is doing remarkably well at the internship, and believes she will be offered a job for the summer.
However, as her internship comes to a close, Mitchum reviews her performance and tells her he thinks she "don't got it" as a journalist because she never spoke up with her opinions. Rory is devastated, and later convinces Logan to steal a yacht with her because she needs to "take to the sea." Rory is arrested for the crime, and after some thought, she decides to take time off from school which causes a rift between her and her mother who believes the decision is a mistake. During her time off in Season 6, Rory moves in with her grandparents because her mother tells her moving back home isn't an option. Lorelai believed her parents would help her convince Rory to continue school, but they went behind her back and allowed Rory to move in with them. They secure her a job at the D.A.R. (Daughters of the American Revolution) where her grandmother is president. Rory seems to have no intention of returning to school as she works through the Fall semester and parties with Logan and his friends. She doesn't talk with her mother willingly. She turns 21, and mourns the idea of not spending the much-anticipated birthday with Lorelai (as they had planned a trip to Atlantic City).
Her grandmother throws her a birthday party, and she invites Lorelai and Luke. They have an awkward encounter, and Lorelai and Luke depart when they feel their dues have been done. When Jess, Rory's ex-boyfriend, surprises her with a novel he penned, they go to a disastrous dinner the following night. Jess confronts her about her current life, and states that her dropping out of Yale is entirely unlike her. His speech inspires Rory to get her life back on track, and she returns to Yale in the spring. She also reconciles with her mother. As Rory's time at Yale dwindles, she is hoping to receive an internship at the New York Times, her dream job. When a rejection letter arrives in the mail, she is shocked. Lorelai later states that "Rory is used to getting what Rory wants." The rejection letter sets her spirits back some as she was anticipating moving to New York following graduation, and she even attempts to go after a job she had turned down. Eventually, Rory comes to accept that she doesn't know exactly where she is going following graduation.
At her graduation party, however, Logan proposes. Rory is still mulling over the proposal when she goes through the graduation ceremony with her mother, father, and grandparents in attendance. She finds Logan after the ceremony is over. After some serious thought, she turns his proposal down because she has come to like the idea of everything being wide open. Her time at Yale and their relationship are now over. Rory and Lorelai plan a rollercoaster filled trip for the summer, but Rory suddenly arrives at the Friday night dinner later that week to announce that she has been offered a job. She is going to be leaving for Iowa in two days to be a reporter on Obama's campaign. Rory departs Stars Hollow to begin her life as a journalist after a tearful and heartfelt goodbye from her family and friends in the little town.
- Main article: Lane and Rory
Rory and Lane meet as young children, and quickly become best friends— remaining so all throughout their teenage years and beyond, even when their lives divulge into seperate paths as Rory attends Yale and Lane decides to stay in Stars Hollow and follow her calling to be a drummer. Rory often helped Lane sneak junk food and “contraband” music from Lane’s oppressively strict mother, and the pair continue to swap troubles as they grow older. The distance Yale puts between them occasionally rears its head, but usually they’re always there for one another, in both good times and bad.
- Main article: Rory and Dean
Rory and Dean meet as Rory's leaving Stars Hollow High, prompting her to question her future at Chilton. Their encounter is a classic meet-cute and Rory the fast-talker becomes Rory the clam as she feels classically teen awkward in her first conversation with Dean – for a while anyway.
Their romance is sweet, starting slowly and evolving into a first love for Rory, which is proven when she has trouble accepting how strong her feelings for Dean are. They seem to grow apart quite a bit after Jess moves to town and Rory finds herself falling for him, though unable to accept it at first. Following her eventual romance with Jess, they reconnect and sleep together while Dean is married. Following Dean's divorce they try dating, but Dean quickly faces that they have nothing in common anymore.
Rory and Paris share a complicated friendship, simply because of Paris’s difficult personality and her constant need to be the best at everything. This causes issues for Rory, who is fairly non-competitive and instead chooses to focus on her own goals— a concept lost on Paris, who makes much of Rory’s time at Chilton difficult. The pair eventually bond over their shared lack of interest in parties and other typical “high school” activies, like dating around or drinking. This leads to a fairly solid friendship, which withstands Paris’s rejection from Harvard— which Rory is accepted to— and results in both girls attending Yale together and sharing a dorm. They end up living together for most of their time there, except for the short break in which Rory dropped out of Yale, though they reunite when Rory returns and she, Paris, and Doyle (Paris’s then-boyfriend) share a dingy apartment off-campus. Paris and Rory’s friendship is once again tested when Paris is voted out of her position as editor of the Yale Daily News; a spot which is filled by Rory, who is chosen by popular demand. This results in Paris kicking Rory out of the apartment and forcing her to live with Logan, though the pair reunites when they both end up broken-hearted at the same time, and very briefly resolve to live together again before both get back together with their boyfriends in the same night. This marks the end of their fight and thus the reestablishment of their friendship.
- Main page: Jess and Rory
Jess and Rory meet when Jess arrives unceremoniously in Stars Hollow, after being sent to live with Luke by his flake of a mother. While Jess is hurt and uncomfortable with the situation and doesn't take well to anyone, he accepts Rory right away in spite of himself and they share a 'meeting-of-the-minds' later that evening in the center of town. While their mutual attraction is quickly evident, Rory battles with herself over the idea that she should remain with her first boyfriend forever, while Jess unapologetically flirts with Rory at every turn. Rory's heart eventually wins over her head and she kisses Jess, and a few months later they finally begin a romance. As the two have exceptionally bad timing, with Jess' family issues, they part and see each other once a year later, with unpleasant results. A few weeks after Rory turns 21, they meet again and Jess has gotten through his family troubles on his own and started a life for himself – including becoming a writer.
Rory meets Marty in her first year at Yale. He sleeps in the hallway after a party - without any clothes on. She wakes him up and gives him something to wear so he can get back to his room without anybody noticing what had happened. After this incident, their friendship grows and he even admits that he has a crush on her, but Rory is already in love with Logan. Marty later starts a relationship with Lucy, behaving as if he and Rory didn't know each other. When Lucy finds out, she breaks up with him, making Rory feel guilty.
- Main article: Rory and Logan
Rory meets Logan through Marty, when Logan and his posse bump into and degrade Marty, which Rory naturally takes offense to. In spite of herself, Rory's impressed with Logan's quick wit and knowledge and is drawn to him, their interactions consisting of banter and flirtation.
Rory and Logan soon begin a fling but, finding she wants more, Rory ends it only to have Logan accept the idea of starting a relationship. Emily & Richard are thrilled by their relationship, as they are friends with his family, and Lorelai worries. Following their boat theft and Rory moving into the Gilmore mansion, they carry on as usual. At the end of the final season, Logan proposes at Rory's graduation party but she declines.
Madeleine and Louise are friends of Paris' at Chilton, or really more so like a posse of sorts. They are not very ambitious students and show more interest in boys, parties and fashion. While Rory's relationship with them is usually dependent on the status between Rory and Paris, they eventually all become friends. Madeline is usually kind to Rory and most times oblivious when the Trifecta are at war with Rory, while Louise is incredibly smart and very astute to Paris' behavior. Rory later meets them again in Florida at the spring parties and they once show up in Yale - for a party as well, of course.
Lucy and Olivia are two girls that Rory meets and befriends during her senior year at Yale. The two are art students and differ from Rory's usual crowd, but they three form a much more typical girl group type of friendship, which Rory hasn't experienced before. She even brings them home to visit Stars Hollow with her, where she has a little break down, because everybody knows exactly what to do after graduation except for her. Rory and Lucy have a fight concerning Marty in Season 7. However, they manage to work it all out.
- ‶Well, then you can say that they exposed you to a world you wouldn’t have otherwise known. Isn’t that what great writing's all about?″
- —Rory hanging out with Paris and Jess[src]
- ‶I'm not a mouse?″
- —Rory doubting her personality[src]
- ‶Special, like ‘Stop eating the paste’, special?″
- —Rory to Logan[src]
- As a child she went on a pony ride. The pony died while she was on it. This traumatized Rory, and she refused to go on a horse ride with Lorelai because of it.
- At 6 Rory took a cheerleading class at Miss Patty's School of Ballet. She wouldn't cheer for any other school than Harvard.
- Rory loves to read and has an extensive book collection.
- Her first D-grade was in Max Medina's English class at Chilton.
- Davey, Sookie's son, is her godson.
- On her birthday, Lorelai always tells her the story of her birth.
- She was born at exactly 4:03am (as Lorelai tells it)
- Luke baked her a coffee cake and blew up balloons at a special table for her sweet 16th birthday.
- One time, Rory tried to drag her mother to parent teacher conferences at 6 in the morning. The school wasn't even open yet.
- She graduated from Chilton as valedictorian with a 4.2 GPA.
- Her idol is Christiane Amanpour. She eventually meets her at the Dragonfly Inn. 
- She was in German and French club at Stars Hollow High.
- She has mentioned that she can speak some Spanish and French and has taken Latin. Later at Yale she has mentioned that she's considering learning Russian.
- On her last day at Stars Hollow High, she dressed up for gym and played volleyball, which is extremely atypical of Rory.
- She was born during a snowstorm.
- Rory wouldn't step on wet grass until she was three years old.
- She won't go near the stove because her mother used to tell her that it was the Devil's hands.
- It took her four months to learn how to ride a bike.
- Her arrangement for Yale is as follows: 5 years after graduating with her BA (or 7 years after her MA) she has to start paying her grandparents back.
- Rory lives between different worlds, the world of her mother where she is surrounded with love, inspirational books, movies, music, and a simple but happy small-town-life, and on the other side the world of her grandparents, where things like perfectionism, luxury, money and idealism are leading.
- Rory Gilmore and Why We Need Better Fictional Journalism (VULTURE • NOVEMBER 2016)
- 'Gilmore Girls' has a problem with Rory's sex life (BUSINESS INSIDER • AUGUST 2020)