In this episode, Luke is dismayed to learn Jess has been indulging in petty theft. Is this the “trouble” he was headed for in New York, or is this something Jess is doing for attention, in defiance of being sent to Stars Hollow, or out of boredom?
Or is it a sort of one-sided joke or prank, where he fulfils the image the town has of him as a criminal by performing mildly illegal acts that do little harm, just to see how upset the townsfolk will become?
Another possibility: Jess only seems to start stealing after he meets Rory. Is he trying to make himself a notorious figure, spoken of everywhere, so she cannot ignore or forget him? After all, there’s no such thing as bad publicity …
It’s also interesting to see where Jess steals from in this episode. He is first caught stealing beer from Lorelai’s fridge. Next he steals a few coins from the bridge repair fund – the same community project that Lorelai and Rory worked on (in a town as gossipy as Stars Hollow, it wouldn’t be hard for the quiet, watchful Jess to learn of that). Then he steals a garden gnome from Babette, Lorelai and Rory’s next door neighbour. Later it transpires that the first thing he took without asking was one of Rory’s books.
The thefts don’t seem to have random victims – they are all connected with Lorelai and Rory. Are they a bit of payback for Lorelai, for trying to give him advice, or are they are an attempt to keep himself within Rory’s orbit, by fair means or foul?