Gilmore Girls : Eight O'Clock at the Oasis (2002)
Directed by Joe Ann Fogle / Joe Anne Fogle
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Synopsis by Hal Erickson
Attending a society auction with Michel (Yanic Truesdale), Lorelai is mildly attracted to Peyton Sanders (Jon Hamm), scion of a wealthy family. Emily (Kelly Bishop) encourages Lorelai to cultivate a relationship with Sanders -- even after Lorelai has come to the conclusion that the man is a crashing bore. Meanwhile, Rory (Alexis Bledel) agrees to take care of the lawn belonging to her weird neighbor Dwight (Jason Kravits), but is unable to shut off the sprinkler system -- a minor inconvenience that leads to major complications when Jess (Milo Ventimiglia) shows up to help Rory out.