Cyndra Rae (cyndrarae) wrote,
Cyndra Rae

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Fic: Sleeping with the Enemy (Gilmore Girls, Jess/Dean) (13/16)

Previous Chapters: One | Two | Three | Four | Five | Six | Seven | Eight | Nine | Ten | Eleven | Twelve

Chapter 13…

Time passed slowly, excruciatingly so, in quiet disconcertedness.

Dillon told Jess that it’d pass, that Jess would get over it, man he had to, sooner or later. Jess had been waiting three months, five days and a few hours now. Not happening so far.

And it wasn’t for lack of trying, at all. Jess had not called Luke since he left. The couple of times Luke’s name flashed on his cell phone’s display, he didn’t pick up. He didn’t call back either. He threw away the Kissinger book because the smell of the several years old, slightly musty paper had turned into a full sensory reminder of all the nights he’d stayed up watching a beautiful boy sleeping peacefully.

And it wasn’t that Jess was moping around, being useless around the loft or at work. Fact he’d never been as productive as he was since he came back, throwing himself and everything he had into the business with absolute vehemence. It obviously had seemed to be working for… Mr. You-know-who. Jess just followed his lead and did his best to exhaust himself completely and utterly, just so he could sleep like the dead at night.

No ethereal visions of almond-shaped eyes blinking open lazily in the early morning sunlight, no floppy sandy hair curling at the base of a slender pale-white neck, no swollen red lips twisted into mischievous little smirks teasing him. None of that fucking bullshit.

And yet, Jess couldn’t understand why he sometimes woke up to a moist pillow under his face. It wasn’t like he could ever remember any of his dreams.


Twenty-three year old Dillon Matthews made it his life’s mission to set Jess up, with girls first and later boys too… sometimes one of each within the same night.

At first Jess resisted – which apparently just served as a blatant admission to the fact that he wasn’t doing as alright as he’d have his friends believe. Eventually he gave in, and went out with (and rejected, or got rejected by) random folks for awhile… until he met Seth.

Seth was two years older to Jess, a fresh college graduate now working as a management trainee with Goldman Sachs. And boy did they work him hard.

He was tall too, about six feet one with chestnut hair (close cropped, not long and goofy like in Jess’ dreams) and had gorgeous blue eyes (not hazel). He was smart and well-read, and had a killer sense of humor. He had none of the airs one would associate with an Ivy Leaguer but most important of all, he didn’t seem to take life too seriously.

Easy kinda guy. Like Jess.

He was pretty resilient to what had once been described as Jess’ caustic tongue, and was both emotionally and intellectually mature enough to match Jess wit for wit, giving back just as good as he got. It never actually felt like they were arguing, even when they were arguing.

Jess loved that.

Course love was too strong a word to use. And being in love was not even in question. Come on, they’d only been out like eight times in three weeks. Too early for sentimental nonsense like that, obviously.

Like it’d been too early back in summer with Dean, right?

Three months, five days and nine hours.

The more he chided himself for keeping count of the days and freaking hours like a chump, the more he did it anyway. It was this pathetic counter ticking away relentlessly inside his head that drove Jess to see Seth more. He was the only one talkative enough and distracting enough to be able to drown the damn thing out, if only for a little while. Seth was, in a lot of ways, similar and yet the exact antithesis to Forester. The differences Jess enjoyed; the similarities he tried his best to ignore.

It was a mildly chilly Saturday night in October, and Jess was accompanying Seth to one of his friend’s house party in the Upper East Side. They took the subway, fully intending to get smashed so neither of them would be in a position to drive later.

“You sure you want me there?” He asked for like a hundredth time.

Seth, for the hundredth time, chuckled and shook his head in exasperation. “You’ll be fine, Jess. Come on, it’s just a bunch of guys from school.”

School being Yale, to be exact.

Jess wasn’t one to be intimidated by smart folks who went to college. Hell, he could bet he was better read than the whole bunch of them put together. But he sure wasn’t about to let his guard down around them prissy yuppie rich-kid types, just in case.

“Admit it. You just wanna show me off as your latest nubile conquest to your greasy old class of 2006.”

Seth laughed, a sparkling laughter that reminded Jess of another set of muted sounds of amusement that always had to be hushed up quickly so they wouldn’t wake anyone in the middle of the night. It pained him to realize he never did hear this kind of loud, full-blown, carefree, bellowing laughter from Dean. Like, ever.


As expected, the Upper East Side mansion they entered was humongous and grand. The party was in full swing up on the terrace. Much to Jess’ chagrin, Seth had conveniently neglected to mention the theme of the night: Cigars, Sake, and Sushi.

A brief (too long) round of introductions later, Jess slipped away from Seth’s side as tactfully (not) as he could. The future investment banker frowned, not liking the sudden emptiness in his hand that’d been clutching at Jess’ arm. But he knew Jess well enough to let him be and turned his attention to catching up with some of his old posse.

Jess strolled around the terrace for a bit, and nearly jumped with joy when he found a tub on the far side of the banquet table filled with ice and generous amounts of beer. He cracked one open and took a long, satisfying gulp before leaning against the table. That’s when he took the time to look around the terrace: everyone had stuck to the night’s dress code of all black, including Seth and himself. Everyone, that is, except one – a tall girl in a wine red knee-length dress and recently shortened, dark hair – the girl who was looking right back at him with bright, piercing eyes.

In hindsight, he probably should have expected to run into Rory Gilmore at this Yale reunion party. He’d never have showed up if he had, obviously.

“Small world,” she drawled as she walked up to him, smiling.

Jess smiled back shortly and they clanked their beer and wine glasses together, making a toast to… whatever it was Rory rambled on about for the next forty seconds and Jess made no attempt whatsoever to pay attention to.

“So, you’re here with Seth?”

Jess took a swig of beer and looked Rory in the eye, waited for her to say whatever she had on her mind.

“I’d heard rumors…”

“Yeah, well, now you know.”

Jess threw the empty can of beer and picked up another, wishing she would just go away.

“Relax, Jess, I think Seth’s great, and you two look good together. Of course, it doesn’t surprise me that you managed to move on so fast.”

Jess rolled his eyes. It had been three years since they broke up, for God’s sake. Who did she think she was?

“What do you want me to do, Rory? Pine and brood over you for the rest of my life?”

Rory scoffed, the light in her eyes dimming momentarily before she looked away and at the crowd milling about on the mansion terrace.

“I wasn’t talking about me.”

Jess started.

“Stars Hollow is a small town, Jess. And I mean small. Tiny, miniscule, microscopic in fact. People talk. Especially when you make no attempts at discretion whatsoever.”


“Did you really think no one noticed the daily lunch dates and the clumsy scaling of trees to climb into bedroom windows in the middle of the night?”

“I… I didn’t…”

Rory turned to him again. “It’s probably for the best anyway. That guy,” she whistled offhandedly. “That one’s got way too many problems for one person to handle, really.”

Jess looked away, clenching his fists trying to gulp down the sudden burst of rage in his gut along with the beer. But he kept his mouth shut.

“I mean, seriously. The boy leaves a perfectly good seat in college, granted it’s only State-U but it’s a degree right, to do what? Pay off his dad’s bad debts so his mom and sis don’t have to lose their home?”

“What’s wrong with that?”

“Nothing, of course! Can’t blame him for trying to cash in on what he does best. Manual labor is all he knows. Never did give himself a chance to learn any better, did he?”

Jess was starting to lose it. “That’s always been your problem, Gilmore. No one is ever rich enough or smart enough or classy enough or freakin’ white collar enough for you.”

“Look who’s talking! You’re the one who’s found all of that and more in Seth Meyer there, heir apparent to Meyer & Shaw Holdings, Incorporated.”

Jess did not care to explain to her that Seth was a fiercely independent guy and wanted nothing to do with his dad’s investment firm. He was too ruffled by the insinuations directed at Dean instead, more than he'd like to be.

“So that’s what you’re riding me about? You want Seth now?”

“Why not? You left that overgrown bag of issues behind for Seth, didn’t you? Hell I don’t blame you at all, Jess. If I heard it right, and how could I not, my mom was right there in the store two aisles down when you put your incredibly lucrative business proposition before Dean…”

Jess’ eyes went wide. “Lorelei was there?”

Rory blinked once in affirmative. “But hey, about your business plan... did the big dumb oaf get it? Of course not.”

“Shut up, Rory! You have no idea what you’re talking about!”

“Oh really? Enlighten me then!”

Jess barely kept himself from smashing the bottle of Sam Adams into the girl’s face.

“I sprang it on him out of nowhere, he was taken aback. And it’s a big decision, he… he just didn’t know how to react! And… he’s got all these responsibilities. Maybe he needed time to think about it, maybe he needed to speak to his family first and… and think about it. He’d only like, really known me for less than three weeks! Someone like him, with so many people depending on him, he can’t afford to take too many gambles right now. And, I mean, come on – I’m Jess Mariano! How could he trust me blindly? I gave him no reason to… to…”


Jess caught himself in the middle of his frantically defensive rant and suddenly halted, to finally look up at Rory. Her eyes were sparkling with sympathy.

Jess felt out of breath, out of sorts, like he’d been running uphill after something and he couldn’t even remember what it was anymore. He turned, walking away despite his legs that felt like they were turned to lead, dragging them until he reached the end of the terrace and leaned against the far railing. He still couldn’t breathe.

Rory approached him slowly from behind.

“Why did you walk away, Jess? Why didn’t you give him another chance?”

To be honest, he’d been asking himself that question for three months, five days and… eleven hours now. Why did he let his stupid pride get in the way of the only thing that had grown to matter to him so much?

“He said… he said it wasn’t enough. What we-we had, it wasn’t enough for him to… go changing his whole life for me.”

Tears filled his eyes but he squeezed them shut, not willing to give in to his pent-up emotions of loss and desperation yet. Not yet.

Rory heaved a long sigh and came to lean against the railing, her shoulder grazing soothingly against Jess’. He still didn’t know why she was doing this, why she was here talking to him about Dean at all.

“Wish it were that simple, huh? Life would be so awesomely easy if we just… knew what we wanted from it. I don’t know about you but by the time I figure stuff out, it’s usually too late. Life moves on, leaving me behind.”

He found himself leaning his weight against Rory, his thoughts circling inside his head around one singular, vivid image.

“H-How is he?”

Rory shrugged. “Okay, I guess.”

“Sleepwalking still?”

“Sleepwalking still.”

Jess winced and closed his eyes tight. “I’m sure Luke’s taking care of that.”

“He can’t anymore. Well, some days he tries.”

Jess froze. “Wh-what do you mean?”

“Luke didn’t tell you?”

Jess tried not to think of the multiple phone calls he’d deliberately missed. “Tell me what?”

Rory bit her lip and looked down at her shoes.

“Dean doesn’t sleepwalk to the diner anymore.”


Next Chapter
Tags: fic: gg: sleeping with the enemy, misc fic

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