Summary: Jess never went to Stars Hollow, continuing down a bad path living in New York, eventually getting punished with community service, where he happens to bump into a certain Gilmore fresh from her yacht-stealing escapades. Lit. Set around 6x03 and onwards.

A/N: Oops, I went and started a new story. Again. When I already have two stories still in progress. Oops. That's why this is just a very, very short introduction-y chapter, and this fic will not be touched, mentioned or even thought about until There's The Rub is all over and done with. Well, that's a lie, since I constantly have lines of dialogue running through my head, so that thought about one should be discounted...Anyway, this was basically a bit of fun. As much as I love Mature!Jess, my favourite will always be sarcastic, chip-on-his-shoulder Jess, and I just can't change that no matter how many times I watch his season 6 episodes. Anyway, at this time I always think Rory acts kind of spoilt, well, she acts spoilt a lot of the time, and no one ever calls her on it, so this idea just popped into my head. But, yeah, I'm babbling: enjoy, I hope.

A mild sense of irritation had been prickling at the edge of Rory Gilmore's consciousness for the duration of her community service that day. It really was stupid, just a little, tiny, niggly thing. It was the study tree all over again and, God, she should have learnt her lesson from that experience; if a Yale student hadn't reacted particularly well to her somewhat quirky needs then it was highly unlikely that a person being forced to do community service would react much better. And yet, for some inexplicable reason, she'd let this stupid little thing get to her and this had resulted in her current frustration.

She'd gotten it into her pretty little head that it was a good idea to march up to the surly-looking, sarcastic, admittedly attractive, new guy and issue what she thought was a perfectly polite request.

"Excuse me, I'm sorry, it's just that that garbage picker thing – whatever it is you call it – is the one I always use and I was just wondering if you wouldn't mind trading?" she asked, faltering slightly under his probing gaze, his chocolate eyes glinting with a mixture of amusement and annoyance. Uncomfortable, she continued to babble, "It's just that it's the only one that's exactly the right height for me and the top part's kinda moulded to my hand, and it took me days to find one as perfect as Don and – "

"Don?" he cut her off at last, raising his eyebrows. The sound of his voice for the first time caused her to hesitate.

"Yeah, I- I named him – it – Don," she clarified, feebly, starting to see how petty this whole thing was.

"Huh," was all she got in response, before he turned to face away from her, continuing to work as though he'd never been interrupted.

Rory glared at him, feeling affronted; regardless of how silly her gripe with him was, the guy was just being plain rude. She took a moment to examine him while he was facing away from her. He was around her height – which meant Don would be the perfect height for him, too, she thought, bitterly, glaring at him harder. He had quite messy chestnut hair that she'd probably have found cute usually but, in her current state of mind, was just further evidence of the guy's laziness and general lack of care for anything, be it hair or lovingly named cleaning utensils. She noted with further annoyance that there was a Hemingway novel sticking out of his back pocket; was this guy designed to infuriate her? Riled, she walked back around into his line of vision.

"Excuse me," she repeated, in a harsher tone than before. "You could at least answer me instead of ignoring me like a five year old."

"I'm not the one naming garbage disposal utensils," he replied, in that delightful sarcastic way that Rory was beginning to become accustomed to from him.

"You know what? Fine. I had a nice rhythm here, long before you reared your gel-covered, Hemingway-reading head, and Don was part of that, but if you want to be a jerk about it, fine."

"Huh, interesting that your gaze immediately goes to my back pocket," he replied, smirking.

She rolled her eyes, blushing, "Don't flatter yourself. I just happened to notice the name of one of the world's most dull writers protruding from your pocket, okay?"

"You're cracked."

"As well-reasoned an argument as that is, I have yet to see anything from a Hemingway novel that could compare to anything of actual substance," Rory persisted, exaggerating slightly in her satisfaction at having found a topic that annoyed him.

He rolled his eyes, "So what are you reading that's of so much substance?"

"I'm re-reading The Age of Innocence," she replied, defiantly.

"Please," he scoffed.

"Please what? It's a great novel."

"Wharton spends more time describing the settings and the clothing than the actual plot."

"It's about the social trappings of that time! The clothing and settings are all a part of the carefully crafted society in which Archer and Olenska have to live."

"Whatever," he said, turning away again.

"Look, will you just give me the stupid garbage picker?" Rory asked, unsure why she was holding onto this petty argument, while – although she'd never admit it – kind of enjoying the back-and-forth banter.

He turned back around, the amusement drained from his face, leaving carefully controlled irritation, "So, what was it? A Ferrari? A jet? A golf cart?"

"What?" Rory asked, thrown off-guard.

"The thing you stole. I figure you're not the type to want to rob anything major, and you wouldn't be here voluntarily, unless it's to spend quality time with Don, so that leaves joy rides and drug possession, and I thought the former seemed more likely.

Rory glared at him a moment, before muttering, "It was a yacht."

He shrugged, "Figures."

"What is that supposed to mean?"

"You just seem the type to steal something stupid, superfluous and not yours. You know: spoilt."

Rory gaped at him with a mixture of incredulity and outrage, "Excuse me?"

"You rich kids feel entitled to whatever you want: yachts, trust funds, and garbage pickers, apparently..."

Rory held back a growl of frustration, as she began just blurting out disjointed sentences. "I'm not rich, and- and I don't have- and Don, and..." she trailed off, before exclaiming, "Fine! Keep him – it – whatever!" and storming off.

What a jerk.

The next day, Rory went to sign in for that day, and found Don leaning next to where her community service jacket was hanging up, with a novel on the floor next to it: For Whom the Bell Tolls by Hemingway. Flicking through, she saw a lot of cramped notes in the margin, and then, written on the front page:

Give it another try, maybe it'll keep you from anymore grand theft boating you've got planned.

Oh, and keep Don, since you two seem to have such a deep emotional connection to each other.

Jess

Rory bit back her grin as she remembered she was still annoyed with him for his judging of her the day before. Her curiosity aroused, she shoved the novel in her bag, wanting to see how he could possibly have so much to write on the painful Ernest Hemingway before putting on her jacket and turning back to Don with a smile.

"Aw, I missed you, boy!"

A/N: Sorry if the whole Don thing seems OOC, but hey, this is the girl who gave someone a twenty for a seat by a tree, she gets obsessive about inanimate objects. Anyway, please review! I just want to see if anyone's interested in seeing this continued, because I don't know if I will or not.