Jess Moves In
Rory meets Luke's seventeen year old nephew, Jess (Milo Ventimiligia), during the season two episode, "Nick & Nora/Sid & Nancy."

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Gilmore Girls Season 2 Episode 5 Quotes

Luke: Me? Raising a kid? I don't even like kids. They're always sticky like they've got jam on their hands. Even if there's no jam in the house, somehow, they've always got jam on their hands! I'm not the right guy to deal with that. I have no patience for jam hands!
Lorelai: First of all, Jess is 17 so I think he's probably pass the jam hands stage by now. Second of all, you can do this. If you want to you are totally capable.

Rory: Good night, Dodger.
Jess: What?
Rory: Figure it out.
Jess: Oliver Twist.