This episode, one of the more complex in structure, has a series of flashbacks within it. In the first flashback, we see a teenaged Lorelai and Christopher coming to the Gilmore home after school. They are wearing the same uniform, although I don’t think the show ever mentions them attending the same school. We know it is December, because they have finished their midterm exams, and are discussing the upcoming Christmas vacation.
With no adult supervision (Richard and Emily are out, and the maid has been fired, of course), Christopher – naturally – heads straight to the liquor cabinet and pours them drinks. Getting Lorelai drunk seems to be part of his technique.
Christopher reveals that his plan (more of a dream, actually), is to take a year off after graduation and go backpacking around Europe. He asks Lorelai to come with him, and she agrees – just as she and Rory are planning to go backpacking around Europe as soon as Rory graduates. During the conversation, it is clear that Christopher and Lorelai are close friends, not boyfriend and girlfriend, and that Christopher would like something more. By the end of the scene, they are kissing, although it is unclear whether this is the first time or not.
The young Lorelai and Christopher are played by Chelsea Brummet and Phillip Van Dyke. Brummet would later become a regular on kid’s sketch comedy show, All That, and Van Dyke had previously been on several TV shows, including Hey Arnold, and The Amanda Show. His acting career finished in 2003.
The Annotated Gilmore Girls 