A/N: Italicized lines are from Romeo and Juliet, Act 2 Scene 2, better known as the balcony scene ("O Romeo, Romeo! Wherefore art thou, Romeo?"). Look it up at Bartleby.com if you're interested.
Although I love "Gilmore Girls," this is the first time I've made a foray into the fandom as a writer; I'm unfamiliar with the ship terms you use, so if anyone could provide a link or help me out with it, I'd really appreciate it. I began this a long while ago, actually, so it's kind of lost in time, floating between episodes that I've no clue how to reference. It can be placed almost anywhere near the beginning or end of the Literati plot arc, and could even be after an imagined breakup.
This, as far as I know, is a one-shot, but when I write Harry Potter one-shots (don't laugh) that are well-received, I usually end up writing more to it. Certainly, if I get positive response and am inspired, I may continue this. Then again, it seems hard to continue. This isn't very long, ends very definitely, and would need work put into it; I'm aware that currently it's on the mediocre side and short to boot.
FYI, the long form of Rory and coincidentally the name of her mother is spelt Lorelai, not Lorelei as it would normally be. My sister bought one of the novelizations of it. So now that you know, don't correct me like my spell-checker did.

Parallel

She was the first thing he saw, coming into the diner at an early hour after pulling a successful trick. He knew by the uniform, the square set of the shoulders as she huddled over her overlarge mug, the hair pulled back conservatively as always. Had he really never pulled off that elastic holding it together?

Something held him back from making her aware of his presence. When she did notice him, he knew why. It was the element of surprise, setting a look on her face of cringing and foreboding of disaster. She had the complacence of having a comeback to whatever he threw at her; therefore, he did not talk, deriving satisfaction from it. She steeled herself for an encounter with him, unconsciously insulting him with the implication that he was difficult and needed preparation to confront.

They sat in a silence received differently by both. Rory, he could tell, was intensely uncomfortable but too proud to be the first to speak. He basked in her obvious embarrassment. She embodied modesty.

I'll prove more true than those who have more cunning to be strange.

Not to speak to her was a punishment of sorts, yes. She of all people knew that.

As he busied himself, far more diligently than he would without her watchful presence, she spoke.

She speaks! O speak again, bright angel! he joked to himself.

"You know I'm here, Jess."

"If we have anything to say to each other, inform me of it, Rory." He held out his arms and scoffed. "Didn't know there was anything left to talk about."

"Yes, there is, and you know it."

"Grow up, Rory," he said savagely, grabbing a rag and wiping the counter. "Do you really think you matter? Hick town girl meets urbane boy and suddenly he forgets everything, right? You harp on the little things and take me seriously. That's all." He shrugs. "If you weren't a customer, I'd tell you to leave."

She was surprised, and more than a little hurt. "I... I just thought..." Her voice dropped down to a whisper and he didn't hear what she said.

"Well, don't think. You think too much, Rory, that's your problem." He stared at her menacingly, challenging her to meet her with a glare of her own, knowing she could not. She didn't.

"Friends, Jess. Apparently I was wrong, but I thought we could be friends." Picking up her bag, she headed out of the door.

It was a let down he was unable to answer her properly then, that all he could do as she leaves was yell, "Were we ever?" He hoped she wasn't crying as she stormed out; she looked like she was on the brink of it. Despite his disgust for weeping, Rory ought to be able to indulge in it this once. He certainly forced her to it.

Luke came down, irascible at being awoken, and not soon after Lorelai Gilmore entered.

Jess watched them and marvelled—smirked, rather—at the parallel between Luke and Lorelai, he and Rory. Not that there was any Rory in relation with him. If he concentrated hard enough, if he could harden his heart to her, he could believe that there was no Rory... but when had he ever tried so hard?

When Jess went to bed (remembering with a smile the elaborate prank he pulled at dawn), he called out to Luke, "It's us against the Gilmore girls, isn't it?"

Expecting no more than a petty jibe, Luke looked up sharply and, storming over, pulled Jess out from under the bedcovers.

But Jess was serious, his face intent, his dark eyes staring up at Luke expectantly. Luke was taken aback at his sincerity.

"Jeez, Jess," he said. "Have a little decency for once. You and Rory, fine, but don't go dragging Lorelai into this."

A giggle came from the street. They moved towards the window, peering out like the old women who haunted these windows with over-curious dispositions.

Of course, it was the Gilmores, inseparable, clinging to each other's arms with the confidence of feminine hopes and secrets.

They remained at the window, looking down upon them. The women looked distant; already, they grew fainter, into the night, leaving behind a trail of—of what? Another carpe diem antonym, another pipe dream, another lost encounter?

"Rory!" Jess called from the window, leaning out irrepressibly. Luke stole towards the wall; it was strange that Jess had never known him to be subtle.

She looked up, her laughter fading with her happiness.

...cease thy suit, and leave me to my grief.

"Jess?"

"I just wanted to say good night!" he yelled.

Her face lighted up and she moved closer to him, her mother trying to hold her back.

"Yeah, you too then," she said. "Don't let the bedbugs bite, and so on. You better be reading Ayn Rand while you're there!"

He nodded and shut the curtains, blocking out the light, only to face Luke as he turned away.

"Love, is it?"

Jess glared at him, made a man by the anger twisting his expression.

"Don't you even think of—so I was right, wasn't I?"

"Oh yeah." Luke laughs. "You right... about what?"

"You love her," said Jess. "And don't bother talking to me, I'm in the shower." He stripped off his shirt, aimed it at Luke's head, and ran for the bathroom.

He could not stop thinking about Luke's one stupid little sentence. "Love, is it?" It incensed him to have something like that forced upon him with one sudden change in behaviour: repenting his treatment of Rory.

Love? Whatever.

Had I it written, I would tear the word.

He was nice to her that one time. That was all. So what? He was nice to her just the once, and now Luke jumped to conclusions, and so did Rory, and if he wasn't careful it would end up—

...all my fortunes at thy foot I'll lay
And follow thee my lord throughout the world.

It would end up in commitment. It would end up in love.