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Jess walks home after work, the last of his hangover lingering and beating in the heat. He hates getting drunk like that. When Jess drinks too much his sarcasm sours, words turning bitter in his mouth. He sounds like Liz. Liz got drunk like that at least once a week, yelling at Jess to leave her alone, until pulling him into a hug when she was sober. Why do I drink like that? she'd ask, eyes bloodshot. Why can't I make it through the week without a bottle of wine? Jess figured she wouldn't be interested on his theories about that. When he was seven or eight Liz had been rambling about doing better, pouring all her alcohol away, so one day after school Jess had drained a bottle of wine down the sink, cheeks flushed with excitement. She'd be so proud. When Liz came home from work the smile Jess had envisioned turned into a crumpled face of tears. How could you? she demanded tearfully. I needed that, I need to forget I'm just your mom and this is my life! Liz locked herself in her room for hours until finally Jess was so hungry he made dinner. The electricity bill was paid so he made pasta, and Jess remembers being just tall enough to reach the stove. Eventually Liz emerged, ate dinner with him and even watched a movie, holding Jess closely and covering him in kisses. I'm sorry. Jess had dared to hope she'd change after that, but the next day she bought more wine and next month there was a boyfriend who promised to put Jess in the ER if he ever touched his stuff. The boyfriend didn't last long but the lesson did. Jess never hoped for anything more after that.
Not long after the incident with the wine Jess decided one thing; no matter where his life went he would not turn out like his mother. He wasn't going to cry like her, mess up like her and spend all his time drinking, getting stoned and passing out. Jess never knew his father so couldn't pass judgement on him, but the guy walked out on them so presumably he wasn't exactly a prize. Still, Jess thought, he did have Liz to contend with. Maybe he'd seen Jess and figured he wasn't worth sticking around for, and Jess couldn't even argue he was wrong. If he thought about that Jess would get an uncomfortable tightness in his throat and, to get rid of it would have to blare music or smoke as many cigarettes as needed. Sometimes just one would be enough and sometimes Jess would make his way through most of a packet. Whatever, he thought eventually. The guy wasn't worth caring about and, when Liz was finished with Jess and sent him to Stars Hollow, Jess decided she wasn't worth caring about either. No one was. If you cared about people they'd just screw you over. Jess was done with all of it. Why Liz thought sending Jess to the town which she claimed sent her spiralling was a mystery, but Liz isn't known for rationality, plus Jess didn't care. He wasn't interested in his mother, his uncle or anyone new he'd have to meet. He'd stay the required year or two with his clueless uncle in this joke of a town and then get the hell out. He'd never have to care about anyone ever again.
When he got to Stars Hollow, Jess figured the plan wasn't a bad one. No one there liked him. They decided he was basically a criminal and who was Jess to dissuade them? Like he needed their approval. When his uncle got mad at him for skipping school or pulling a prank, Jess wondered why he was bothering to get mad - it's not as if Jess was doing so well. And yet, for some reason, Luke really seemed to care, and so did this girl, Rory. Her mother didn't - Jess could see the distrust written all over her - but her daughter did. And when he gave her the whole speech about doing whatever, wherever, Rory called him on it. It made Jess rethink things a little. He was smart enough to pass the classes, he'd surprise them. Jess still didn't want to go to college but he'd make it through high school. And then it all went to hell. Jess wanted to tell Luke and Rory but he couldn't - he couldn't stand disappointing them too. He couldn't bear seeing the look Rory would get in her eyes. Jess decided it would be simpler just to leave. He thought that by taking himself out of the relationship he was differing from Liz, not clinging on, but now Jess isn't so sure. He didn't want to hurt Rory but knows he did. Liz would move after any breakup and now, Jess thinks uncomfortably, he ran away too. He left like Jimmy did, like Liz always would. He didn't want to be like either of his parents and it seems he inadvertently copied both.
He has reached the apartment. Jess casts a glance at Rory's scarred car before opening the front door, wondering if she'll ever get it fixed. He wishes he could just give her the money, though he doesn't think Rory would accept it. He finds her at the table, eating a snack out of the box of food Lorelai gave them and Jess shakes his head at the offer of a poptart. Sitting next to her, Jess watches Rory wipe some crumbs from her mouth and tuck a strand of hair behind her ear. Changing his mind, Jess picks up a poptart and bites into it, welcoming the rush of sugar. He hadn't known how hungry he felt until he started eating it, and Jess is grateful to Lorelai for putting the box together, though he imagines it was more for Rory than him. Jess is glad they made up. He has issues with Lorelai, no question, but hated Rory fighting with her over him. He remembers Luke's comment of their being the same person and it gives him pause. A year or two ago Jess would have simply laughed at that, but he's more reflective these days. Maybe that's what a roadtrip does to you. Or maybe it's just getting older. Jess looks back at Rory, wondering what she and Lorelai talked about. She seems more distanced since getting back.
Shaking himself, Jess gets up to make some coffee. He's pouring water into the pot and shrugs when Rory asks, "What do you want to do tomorrow?"
"No idea." Jess misses having extra cash, being able to take Rory to a concert or seeing a dumb movie for the hell of it. Besides the stupidity of drinking so much Jess is annoyed with himself for spending so much at the bar. "What do you want to do?"
"I don't know." The air is quiet between them and Jess turns around.
"I swear I won't get drunk like that again."
"I know," Rory says, sounding surprised. "It's okay."
"I don't drink like that," Jess says. "My mom drank like that."
Rory waits, her expression curious and sympathetic and Jess lets out a breath, wishing he'd left off the last sentence. But isn't he trying not to be like his mother? Liz never told him the full reality of things, drunk or sober, and pushed him away when Jess asked more. He can talk to Rory. He can be real with her.
"Liz drank so she wouldn't have to deal with stuff," Jess says slowly. "She didn't like being a mom. She didn't like her life, period. She said Stars Hollow smothered her and had all these plans, but getting pregnant wrecked it. She talked about wanting more, but it all sounded like some kind of fairytale. She'd marry the first guy who stuck around longer than a month and it ended bad, every time. But she never wanted to do better."
"I'm sorry," Rory says gently and when Jess says quietly, "I don't want to be like that," she gets up and goes to him.
"Jess! You're not like that. You're nothing like Liz."
Jess shrugs. He's hurt people too, he knows, and not been real about stuff. He figured he wouldn't amount to much more than Liz did. She clung to dreams, he dismissed them. Is it better?
"I love you," Rory says seriously. "And you can do so much, Jess. I know you can."
Jess closes his eyes for a moment. He doesn't want to talk about this again. He meant what he said before to Rory, that she and Luke are the same that way. They get angry at him for not doing more, but what is it they're going to do? Rory has her own mind, Jess knows that, and is smart enough to get to wherever she wants to be. She goes to Yale, for crying out loud. And Luke runs his own business, which Jess has to come to respect. She and Luke are so good at things they want to focus on but when something shakes them, they flounder. Why are they trying to fix him? Luke will work out anyone's problems before his own and Rory - put a book in front of her and she'll have read it, analysed it and written a freaking thesis on it before you can ask. But outside of that, she struggles. Jess can see it. He doesn't know what to say to her. She should go back to school, he thinks, but what would he do? Live here? Move there? He loves her but that thought makes him feel uneasy, so Jess pushes it away.
"We can both do a lot," he concedes and Rory's face relaxes into a smile.
"Right! Jess, I'm sorry about taking the notebook to Luke, I am. I promise never to do anything like that again. I just - I really think you could do something with it."
Jess nods and gives her a kiss, which stops Rory talking. She kisses him back and then whispers, "Hey, I know what we can do this weekend, and it doesn't even cost money."
Jess laughs at that, kissing her some more. Late that night, after three rounds of said free activity, Jess wakes up. Rory is sound asleep, lying on her front with her arms stretched. Jess carefully sits up, finding the notebook they fought over and carefully turning on the light. Rory lets out a sigh but stays asleep, frowning in her dreams and after a moment Jess starts to read. Some of it's not so bad. He reads and reads and wonders that if he knew someone else had written it, perhaps he wouldn't dismiss it as easily as he's been doing.