It Should've Been Lorelai

S2 E14: Lorelai and Rory are stunned when Rory's father, Christopher (recurring guest star David Sutcliffe), brings his new girlfriend, Sherry (Madchen Amick - "Twin Peaks"), to Stars Hollow. Sherry makes it obvious that she wants to build a meaningful relationship with Rory. Meanwhile, when Emily learns about Sherry, she becomes furious with Lorelai for failing to win Christopher back.