2x14 - It Should Have Been Lorelai
Lorelai (Lauren Graham) and Rory (Alexis Bledel) are thrown for a loop when Christopher (David Sutcliffe) brings his new girlfriend Sherry (guest star Madchen Amick, "Twin Peaks") to Stars Hollow and she makes it clear that building a close relationship with Rory is her top priority. Meanwhile, when Emily (Kelly Bishop) learns about Sherry, she is furious with Lorelai for blowing her last chance of getting together with Christopher.