LORELAI: Where’d all this come from?
LUKE: Jess. Liz shipped the rest of his stuff last week. He finally unpacked.
Jess moved to Stars Hollow six months ago, and his mother Liz has only just now boxed up all his possessions and had them shipped to Luke. If Jess had any hopes that living with Luke was just an extended vacation, they have now been thoroughly dashed. The knowledge that his mother has truly kicked him out of home and he is stuck in Stars Hollow must come as devastating news. I think we can assume that the Jess we see in this episode is a deeply unhappy boy.
The Annotated Gilmore Girls 