He mother disapproved. All she saw in Jess was Chris, version 2.0. Rory was locked out from the privileged world, but had more opportunities. She got to watch from the sidelines and join in whenever she fit. Lorelai thought this was what made her daughters life fall apart so quickly. Forget midlife crisis when you can have it at 21.
Jess didn't have anything. He was a high school dropout who wrote a book. So much for him being anti-cliché. Sure, she loved the book, but she's rejected him in more different ways than she could count. After the party, they'd been awkward. After the Firelight festival, even more so. And then he asked her away and she chose a married man instead. That stung him for life. Rejection, in the highest form. So he turned his life around. She dated jerks. First Logan, then Alex, then she married Cameron. Apparently Rory wasn't a good trophy wife.
But suddenly she was back on his doorstep. He had no idea what was wrong, but suddenly the stinging was back. He realized it had never gone away. He let her in. She didn't have bags or clothes - just a worn copy of Howl. She stepped through the doorframe, looking at the life he'd created out of nothing. She'd created her life out of everything, and now it was gone.
He hugged her softly and patted her on the back. Suddenly it was 10 years earlier and they were dating. She half-consciously realized that it had always been this way. He had the problems and she fell apart. And the stinging came back. . .