20 Years of Jess Mariano—
Milo Ventimiglia first appeared as Jess on Gilmore Girls in "Nick & Nora/Sid & Nancy" (original air date: October 30th, 2001)
"We always played that Rory and Jess saw each other for what they were. That was the great thing about that relationship. She saw Jess for exactly what he was, and he really got her. So it just seemed like a natural thing [for Jess to pull Rory out of her funk] because you needed somebody to do it. It wasn’t going to be Lorelai, and it just made sense for the relationship that we had set up with them that he would get her." -Amy Sherman-Palladino, Entertainment Weekly