During the episode of Gilmore Girls called Nick & Nora/Sid & Nancy we see first meet Jess. Jess is Luke’s rebellious nephew. He has really become so rebellious that his mom can’t handle him. Since Luke is such a stabilizing influence he really just ends up offering to have Jess come live with him. No one consults Jess or how he’s really going to adjust to life in such a small town and being away from his family and his friends.
In usual Luke fashion he just assumes that he will be able to fix whatever problems might be there even though he has never had kids or doesn’t know a whole lot about them. Lorelai tries to tell him that he’s getting into a lot more than he can handle but Luke refuses to listen because his family needs him. Instead, we see Jess’ arrival in Stars Hollow even though Luke only lives in a small apartment above his diner and there really is no room for him. We immediately see that Jess is going to have a lot of conflict with such a quaint town.