This episode was actually a back door pilot for a proposed spin-off series starring Milo Ventimiglia. It was tentatively titled "Windward Circle". The WB had committed to six episodes of the series, but dropped the project citing cost issues due to filming on location in Venice, California. Ventimiglia then left the series as a regular, making only occasional appearances.
Sherilyn Fenn plays Sasha, the girlfriend of Jess' dad who rocks a super short bleached blonde pixie cut. Later in Seasons 6 and 7 she plays Luke's old high school flame and her hair is back to her natural brown.
This is Alex Borstein's second appearance on this series. Previously in season 1 she was the harp player at Lorelai's Inn. She was originally cast as Sookie St. James.
When Jess is dealing with an old hippie who speaks in platitudes, Jess walks away and sarcastically says, "I'll have the alfalfa sprouts and a plate of mashed yeast." It's what Woody Allen ordered in Annie Hall when he was in Venice
While debating what Emily should wear to her graduation, Rory points out that the ceremony will be held on the lawn. Miss Celine advises against wearing green since they will be on grass. In the next episode, the ceremony is held in the Chilton courtyard on stone.