Lorelai "Rory" Leigh Gilmore is the only daughter of Lorelai Gilmore and the first-born child of Christopher Hayden. For her sophomore year and on, Rory attends the Chilton Academy.
Before leaving Stars Hollow for Chilton, Rory met Dean Forester who became her boyfriend for two and a half seasons. They break it off for Rory to date bad boy Jess Mariano, the nephew of Luke Danes.
After graduating Chilton, Rory goes on to attend Yale where she studies English. After briefly rekindling her relationship with Dean while at college, she starts dating Logan Huntzberger, an heir to a major publishing company.
Lory briefly leaves Yale, but Jess convinces her o return and she does. Aftert graduation from Yale, Jess proposes to her and she declines.
At the end of the series, Rory accepts a job as a journalist to cover Barack Obama's presidential run.
Lorelai: I'm talking about that you take my sweaters and you wear them and you stretch them out.
Rory: I couldn't possibly stretch them out! Your boobs are way bigger than mine.
Lorelai: That is not true.
Rory: Yes it is.
Lorelai: Your boobs are totally bigger than mine!
Rory: You're crazy!
Lorelai: Do you want to measure?
Lorelai: I'm serious. Why don't you get the measuring tape right now?
Rory: I am not going to measure my boobs.
Lorelai: Because you know that you are totally bigger.
Rory: I'm going inside.
Lorelai: Fine, don't measure. We'll just compare bras.
Lorelai: Hey, you didn't wake me up!
Rory: I set the clock.
Lorelai: Yes, but see the clock stops ringing when you throw it against the wall, giving me ample time to fall back asleep. You, however never stop yapping no matter how hard I throw you, thus ensuring the wake up process.