Disclaimer: I do not own Gilmore Girls or any of its characters.

So, my first Gilmore Girl fanfic. Don't really know where this story is going yet, but I guess you guys will just have to read to find out, won't you? Enjoy! And please, don't hesitate to review. Thanks a million!

Chapter I: Shattered

Uncertainty. Jess Mariano was a man of unpredictable measures, unrestrained by the ethical norms of society. He lived life with a sense of adventure, without a care about anyone else but himself. That is, until he met her. Rory Gilmore, a simple, small town girl, with an untainted reputation. She was beautiful, kind, and above all remarkably smart. They were of two different worlds: she was pampered with love and joy from a caring circle of family and friends, while he wandered amidst a solitary sea of pain and neglect. And yet, there was a certain charm about this girl that attracted him. Maybe it was their shared passion for books. Jess was an avid reader, and to find someone who had journeyed through the endless pages of classic volumes as he did enticed him.

And yet, perhaps it was her faith in him. Of anyone is Stars Hollow Rory was the only one who saw the good in him. She trusted in his abilities and intelligence, knowing that he had the potential to be a better person. But he let her down. He lied to her, deceived her, and abandoned her. He had to live with the burden of her disappointment, forever the prisoner of his own guilt. There was no escape.

No. That word continually echoed in his mind. How one simple word could shatter a glass of hopes and dreams. But he shouldn't have expected anything less. Did he really believe she would go away with him? No, of course not. She was too smart for that. Unlike him, she had a life, a future. He had nothing.

"Jess?" called a faint voice. "Jess, are you there?"

Jess groaned lazily, as he tossed the blanket over his head. He was in no mood to get up. It seemed like all of the problems in his life finally took their toll on him.

At the sound of continual knocking at the door Jess sat up and exclaimed, "Go away! I don't want to talk."

The young man stood up and stretched. Scratching his dark disheveled hair, he glanced around his rundown apartment. What a mess. Articles of clothing were scattered everywhere, along with magazines and beer bottles. In one corner of the residence, empty pizza boxes were stacked alongside the wall, near a twenty-year-old TV. Dirty dishes piled within the sink, as the pungent stench of cigarette smoke filled the air.

Once again, the voice on the other side of the door called, "Jess, open this door now! We need to talk!"

"I said go away!" Jess yelled back, as he poured himself a glass of water.

Outside, in the hall, a frustrated young woman sighed. With firm resolve, she stepped back and reached beneath the doormat for the spare key. Jess had been lying on his threadbare mattress reading a book when the girl barged in.

"The next time you decide to go into seclusion, get rid of the spare key first," she scorned, tossing to him the metallic object.

Irritated, Jess sat up and glared at her. "I told you to leave me alone. What part of that don't you understand?"

The young woman just bent down and gazed at him empathetically. For a moment she looked thoughtful until an acrid smell reached her nose.

"Oh, gosh," she exclaimed. "Jess, have you been smoking?"

Jess's jaw tightened as he simply turned away. He was in denial and she knew it. There was something seriously wrong, and he would have had to be a real idiot to think that he could hide it.

"Jess, I've been trying to reach you for two days now. Every time I call, you never pick up, and when I come over, you're never here." She paused, and tried to look into his eyes – those dark eyes of his that seemed to hold so much anger against the world. "Tell me, what's going on with you?"

"Cecilia," he pleaded. "I don't want to talk right now."

"This is about Rory, isn't it?" she asked rather abruptly.

Jess blinked, and then drew in a breath. He didn't reply, but instead dropped his gaze. She knew it; it always went back to Rory. Cecilia sighed, and placed a reassuring hand on his shoulder.

"Jess, you shouldn't–"

"No," he said, pushing her hand away. "She said no."

Cecilia bit her lip as Jess suddenly stood up. For a moment, he paced around the room, as if to gather his thoughts. He finally stopped before her as a look of dejection passed over his rugged face.

"I should have seen it coming. I mean, what was I thinking?"

"Jess," Cecilia began; she gently grabbed his arm.

"It hurt, Cecilia," he confessed. "It hurt a lot." Jess swallowed hard; his gaze was fixed so intently on her that Cecilia dared not move. She felt compelled to speak, but the pain of rejection that clouded his eyes kept her silent.

At long last, he turned away and sighed. "I should have treated her better. Heck, I don't blame her for refusing to go."

And so it was that reality began to hit him. He had lost the one person he truly loved, and this time, there was no chance of getting her back. Cecilia, too, could see that he had come to that revelation. She knew how much Rory meant to Jess, and it troubled her to see him in such a desperate state.

Without warning, she gently embraced him. Although he was caught off guard by the gesture, he didn't resist. It was just what he needed right now. They stayed like that for a moment, until Cecilia pulled away.

"I'm sorry it didn't work out," she said quietly. "But I can't let you throw your life away like this."

Speechless, Jess just turned away and ran his hand through his hair. He hated to admit it, but she was right. It had been two days since the incident with Rory, and he had done nothing but mope around, returning to his old habits of smoking and drinking. He had thrown away all his pride, and he was left with nothing. What else did he have to lose?

"C'mon," Cecilia said, grabbing his hand. "Why don't you go and wash up, and we'll go out to eat? My treat." She smiled.

At first, Jess hesitated; he wasn't exactly feeling sociable at the moment. But, then again, he was starving, and Cecilia's company never failed to cheer him up.

"Alright," he said, smiling meekly. "As long as we're ordering Thai."

Cecilia chuckled. "It's a deal." And with that, she watched him disappear into the bathroom.