The show was first announced for pickup by The WB for the 2000–2001 season on May 16, 2000,[1] a month after the original filming of the pilot episode in April in the Toronto suburb of Unionville.

The central plot point of the season revolves around Rory's acceptance to Chilton, an elite prep school, and Lorelai's need to borrow money from her parents, Emily (Kelly Bishop) and Richard (Edward Herrmann), to fund her daughter's education.

Lorelai's parents agree to lend her the money, but with one condition: she and Rory must attend dinner at their home in nearby Hartford every Friday night until the loan is repaid.

Not long after giving birth to Rory as a teenager, at the age of 16, she left her parents’ home and moved to Stars Hollow to prevent them from imposing their privileged lifestyle on her daughter.

In the pilot episode, Rory meets Dean Forester (Jared Padalecki), a new student at Stars Hollow High School who has a crush on her.

The season shows Rory as having strong friendships with both longtime friend Lane Kim (Keiko Agena) and fellow Chilton student Paris Geller (Liza Weil).

Lorelai has no love interest when the series begins, but she soon develops feelings for Rory's English teacher at Chilton, Max Medina (Scott Cohen).

The site's critical consensus reads, "Warm, cozy, and quirky, Gilmore Girls's two lead characters make the show a standout pick-me-up in the family-friendly genre.