Beth Kennedy

Lorelai's well-intentioned advice doesn't dissuade Luke from reluctantly agreeing to care for his wild 17-year-old nephew Jess (new series star Milo Ventimiglia). Rory finds herself attracted to Jess, the town's newest resident.

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.

On the eve of Sookie's wedding, Lorelai and Christopher (recurring guest star David Sutcliffe) share an intimate night together. However, their discussion of perhaps resuming their relationship ends when Christopher gets an unexpected message from his former girlfriend. Meanwhile, Rory is so happy to see Jess when he returns to Stars Hollow that she surprises him--and herself--by greeting him with a passionate kiss.

Big trouble comes in a small package when Sabrina takes a babysitting job.

When a meeting of the Edgar Allan Poe Society at the Independence Inn is interrupted by a minor fire, Lorelai must find rooms for the guests at various homes around town. Forced to relinquish her bedroom in her own house, Lorelai spends the night at Luke's place. Meanwhile, trying to decide amongst Harvard, Yale and Princeton, Lorelai and Rory make an extensive list of positives and negatives for each college. And Luke worries that Jess may not be attending school when he learns that Jess has been working a surprising number of hours at a local drugstore.