RORY: You facilitated it, you made it happen, so I guess that means that you’re officially a part of our town now.
JESS: Hey, wait a minute.
Having pestered, nagged, and occasionally dragged Jess into helping Luke by working at the diner, just as she gave him a scolding and inspired him to fix Luke’s toaster, Rory now tells him that he is a part of the town. As well as helping Luke, it feels as if Rory was also trying to rehabilitate Jess, or improve his reputation. Jess seems slightly alarmed by this, and rejects the idea that he’s part of Stars Hollow – he’s always seen himself as “on the road”, a freewheeling drifter who’s just on his way through.
Luke worries that he and his uncle Louie were parallel to each other, but in fact it is Jess who is most like his great-uncle, Louie Danes. Both are unpopular in town, and considered to be rude, antisocial pains in the backside, given the cold shoulder by the good folk of Stars Hollow. Maybe like Louie, the town would soon turn forgiving should Jess actually die – a plot line Milo Ventimiglia urged upon the writers of Gilmore Girls, to no avail.
Of course, by roping Jess into helping out, Rory has ensured that she and Jess have spent most of the week (was it a week?) together, and working together respectably in public as well, so that everyone can see they are friends. Notice has exaggeratedly Rory addresses Jess as “friend” and “buddy” while she teases him, letting everyone know that she and Jess are just good friends.
What Dean thought about this volunteer work, we don’t know – he isn’t seen or mentioned in this episode. Since the Bid-on-a-Basket Festival, Dean only shows up in order to play the jealous boyfriend, never to just spend time with Rory or to help her out.
The Annotated Gilmore Girls 