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Jess meets a girl with pale blue eyes. She's smart and pretty and kind and she juts her chin out and stands her ground. Even when she's angry, her eyes look like a deer's and her forehead doesn't even scrunch when she draws her eyebrows together, but her face gets a little red and she purses her lips together. She rarely guards her body language, preferring her arms to her side, unwittingly open, and she doesn't hold her hands in front or behind as a nervous habit, just draws her fingers through her hair, but she never manages to mess up those brown strands of hers. She talks fast, and a lot, and everything she says sounds darling to him and he just wants to find ways to keep her talking. He likes her.
There's not really a chance that she'll ever like him back, meaning that he never exactly tries, just finds ways to spend time with her.
Her boyfriend reminds him of a lot of people, and Jess knows many and likes few, so that's not a good sign. He leaves when she asks him to leave but is more than happy to put himself between her and him to shield her, or to have the adrenaline running to take a swing at him and get away with it. Jess doesn't hit him, but it's close. Next time, he won't miss.
He swerves and crashes her boyfriend's car and she winds up in the hospital while he and Luke mutually decide to send him back to New York. He's done enough damage, is the thing. Liz is like she usually is, he won't shame women for dating except for when it's his mother and she switches boyfriends twice on one particular Sunday, and the one they wind up with for most of his time living with her again isn't a hitter so he's a real charmer.
What surprises him is that Rory picks up his calls and wants to talk to him, and they do. She comes to New York, which has him thinking, and that day they have together is the best he's had in a long while, he's in the city he loves with the girl he likes, and maybe it's stupid but he thinks maybe she likes him too. They walk a bit closer together than they have to, and they seem to gravitate towards each other, when he sneaks glances to her to sneak a smile, she catches him and smiles right back. They're on time, in tune, and right before the bus, he thinks he might kiss her. She's still got a boyfriend, though, he thinks, and if there's one person he doesn't want to be like, it's his mother. He thinks for half a second that she might tug him in by his jacket and then press her lips to his, but she doesn't, she gets on the bus and they say goodbye and then she's gone.
He goes home to nothing, all that happy energy still living vibrantly in the smile he can't quite keep down, and he goes to his room before he comes to face either of his roommates and they subsequently, inevitably ruin his mood.
Liz doesn't want him around. She's had the taste of being motherless and she likes it, doesn't change much for Jess, never has, but he doesn't blame her for it, not really, he is who he is and she is who she is, it's a damn shame if he thinks about it but thinking about it is a choice he doesn't often make. It is what is, essentially, and Jess has learned that you have to accept things as they come because fighting seldom bends the outcome. Push comes to shove, he's sick of her new guy, she's sick of him, and her new guy is sick of both of them. Jess leaves before the guy does, none too excited to see that blow up.
Plus, there's the addition of the fact that Jess is dreaming about a certain shade of blue every night, and he can't focus anymore, too distracted by possibility. It's not an obsession, but it might be.
When he tells Liz he's going, she doesn't much care, which is fine by him because it makes it all easier. By some miracle, Luke takes him back. If he's being honest, though, he's not thinking about his uncle at this time, because he's seventeen and self absorbed. He's too caught up in the only thing in Stars Hollow that he cares about at that moment, she's at a wedding and she's got him hoping and Jess has been told that the damage is done and he shouldn't ruin what Rory and her boyfriend have together.
But Jess is nothing if not a madman out to bite the needle, so he doesn't heed Luke's warning and goes out to do a little damage.
Whatever he's expecting when she walks down the hill to talk to him, he's not actually expecting her to kiss him, and he's not expecting her to run away afterwards. If there was ever a logical line of events, that wasn't it. He can't help but stare after her even when she's left him, he can still taste her and he tries to hold onto it so he can recall it later. He's kissed girls with more technical skill than she has—as if kissing is a blue collar job—but this one is the sweetest and the only one he's wanted more of after it's gone. It's the only kiss he's ever had that's bitten him without teeth, the only one that drags his fingers to his lips as if to touch the ghost of her breath, and the only one that leaves him that he misses.
He doesn't see her for the summer, and she doesn't write to him either, but it's what he should have expected anyway. He came to this stupid town for her, he took a risk, and his risks always miss. It's not like the safe shots he takes are much better. Jess gets restless, and then he gets angry, and then he gets vindictful, spiteful, and there's this blonde girl that he knows has been eyeing him—girls have been known to do that but he rarely pays them mind unless he's had a particularly bad day, which he's pretty sure is mean of him, but they don't seem to care for his reasoning anyway, so long as he's responsive when they ask him to the single-use bathrooms—and he finds out the girl's name is Shane. This is after they've messed around behind the school. He doesn't have to introduce himself to her.
When he kisses her, she kisses back and vice versa. It's nice and predictable, and when he gets the feeling that she's starting to like him, he reminds her that he's a real fuckface and she backs off. And then she comes back.
When Rory deigns to show her face in Stars Hollow again, he can feel her glaring when Shane has got him backed against a tree. It's not that he chose the spot just to piss Rory off, but it is a perk that she sees that she doesn't have him wrapped around her finger like she very well might.
He's not exactly hiding the fact that he still likes Rory, he's more distracting himself from it and in the process, distracting everyone else. Rory seems to have a problem with it, which he'd like to take as a sign, but none of the signs he's read before have gone well for him, so he leaves it. They argue and when they're not arguing but are trapped in each other's space, it simply becomes obvious that they're arguing for the same thing, and may as well be exactly the other person.
When he tells her that Dean's a jerk for breaking up with her in public, she tells him that he's wrong because Dean is right. She's crying on the bridge, and he last did that when he hurt her. It's not that he's ever had a girlfriend before, but if she broke up with him like Dean did Rory, it would be damn good riddance. And that's where their delineation begins, Rory's automatic disposition to see the best in people and turn the fault on herself if something goes wrong as opposed to Jess' instinct to assume the worst and put the blame on anyone else if possible—though, people deserve the blame they get from him. He doesn't start fights, he gets in them enough as is.
It's nice. She is. They are. He has to admit, for once, that he's enjoying himself, and he likes where he is. He and Luke don't often see eye to eye, but he's finally starting to get the feeling that the man is really looking out for him, and has his interests in mind more than any ulterior motives that Jess has thus far been unsuccessful in sussing out. The idea of someone other than himself putting him first is foreign, and he can't decide if he likes it. Liz doesn't call, and he knows he likes that.
Spending time with Rory feels like hanging over a cliff with the rope wrapped between two fingers. The view's nice, but he's pretty sure he's about to fall way, way down. He catches himself in her eyes every now and then, and there's one time that he remembers so vividly that he thinks he'll hold onto the memory forever. They're sitting in her living room, they're unsupervised, and their lips have just parted. She's pressing hers together now, the way she sometimes does like she’s still tasting it, and their foreheads lean on the other. Her face is angled a little low, so her eyes looking at him appear even bigger. He looks at her and feels her breath on him, wonders how his breath feels on her. For fifteen strange seconds, he knows exactly who he is.
Jess is beginning to think he's in love with her.
Though he loses that feeling of certainty when the moment passes, and remembers that he doesn't know where he wants to go or what his future looks like and who he is really is a gigantic question mark, he still recalls that he knows he wants to be hers. He's aware, the entire time, that he keeps falling short of what she deserves and that they're on borrowed time, but when the end comes it still hurts to an unexpected degree. He didn't expect the sting to be that strong. The hit, of course, has come from him. He hurt her, again. And he can't shake the feeling that he fits right into the category of men that he's known all his life that he'd thought (hoped) he was above.
He's mad, he's frustrated, he's bruised, he's not graduating, and he made his girlfriend cry. There are few things that could make the night worse, but a man showing up and claiming to be his father is definitely one of them.
It's an out of body experience, doesn't really feel real, because he doesn't think it has any right to be, and he doesn't know anything anymore but he knows he's angry. He waits for his uncle to get back, waits up and simmers, boils over with a roar once the door opens. He's yelling and gets yelled at right back, which is at least familiar.
Luke tells him to go, so he does, but he doesn't have a car. He has to bus out of Stars Hollow, and when she catches his eye when his book loses him, everything else in the world stops. There's a lot of things to say to her, but he stops being able to breathe. He thinks she knows that he's leaving, his bag is right by his knee and why else would he be on a bus, but he can't bring himself to say the obvious goodbye. So he doesn't and it feels a little open ended which he likes because maybe it means that his time with those pale blue eyes isn't over.
It's one of his more stupid mistakes, really.
He's hitchhiking across the country to California to find a guy that's now walked out on him twice. That's how desperate he is, and it's how he ended up on the road.