From "Nick and Nora/Sid and Nancy". The conversation between Lorelai and Jess goes better than in the show.
"You don't know anything about me or my life, or my mom, or Luke, so why don't you go Dr. Laura someone else?" Jess snapped. He was sick and tired of people assuming things about him just because he preferred not to spill his guts to them. He was tired of running from his past, and too tired to run toward a future of any kind.
"You seem like a nice kid who really got off track." Lorelai nodded. "Pull any stunts around my daughter, and you will be sorry."
"I know." Jess said, almost meekly. "Look, Lorelai, I'm sorry."
"Sorry for...." she prompted him.
"For judging you the minute you came out here." he shrugged. "For taking the beer when I know it will drive Luke nuts. Whatever."
"What happened that got you so messed up?" Lorelai asked.
"Different stuff." Jess shrugged again. "Doesn't matter. Acting this way has gotten me this far."
"But where are you going?" Lorelai asked.
"I guess that's something I'll have to figure out."
"Fair enough." Lorelai nodded. "Just give Luke a chance to help you get started. He's good at that."
"I will." Jess nodded. They returned inside and Luke stopped Lorelai in the kitchen as Jess joined Rory in the living room.
"What did you say to him?" Luke asked.
"That I get where he's coming from, and that if he wants a fresh start, he should let you help him."
"Really?"
"Yeah." Lorelai nodded. "I think that in the long run, he'll turn out okay."
"Good." Luke smiled, and they joined the others in the living room for dinner.