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.