Authors Note: Wow, I only recently heard that Edward Herrmann, the man who played Rory's grandfather, has passed away. So this chapter will be in tribute to him. Thank you to all the reviewers, you're excitement and support make me so happy.

'Then and Now'

With perfect clarity they remembered the last first time they'd seen each other. Rory stood in Truncheon books with a look of uncertainty and hesitation in her eyes – those big blue eyes of hers, still laced with innocence and Jess had stared like the love-struck teenager he'd once been, in awe of the force before him. He'd craved her presence after leaving Stars Hollow; her mind and body had always been alluring. Hidden in her depths were mysteries he'd never solved. She was his puzzle, left half finished but never forgotten. That boy, wrapped in leather, slathered with gel, with a constant chip on his shoulder and hatred towards the whole world, was gone now. Undoubtedly he'd managed to change after Rory, because of her. She'd unlocked within him a passion he'd never known, and its intensity was terrifying. He'd taken her for granted and lost her, everyone knew. Now he had evolved into the man he always had the potential to be, and the residents of Stars Hollow - the ones who had described him as a delinquent, a lost cause, a good-for-nothing bad boy - could see him clearly now.

Rory had also managed to change due to Jess. Once she had been timid, afraid. But being with him, especially at such a young age, had awoken something dangerous and thrilling inside her. He'd inspired her. She'd always been jealous of him, his freedom and his ability to be whomever he wanted when it suited him. Shyness and books and brains had confined Rory, and Jess had been wild and free and chaotic – his fierce rebellious nature had drawn her in, and his intelligence had amazed her, his ability to learn faster then almost everyone she knew. Yet he chose his own path. He knew what he wanted. So as he stood outside the Dragonfly, watching his Uncle marry the woman of his dreams, Jess felt an unbearable jealously towards them. He was happy for them, but he felt like their love, their deep connection, was something he'd never share with someone again.

He watched too Rory, the light in her eyes as she watched her mothers wedding. She truly looked happy – fulfilled in a way he never remembered her being. He guessed accomplishments could do that for a person. She definitely wouldn't recognise him now. He'd traded in the leather for suits and was now an established author. He wrote 'The Subsect', and even had it self-published. But his second book 'The Prevalence' was the one that he was proud of. He was far from rich, but that book had been his baby, the only thing he'd managed to write that he could hold in his hands and be proud of. His first book was a baby step, but his last was a leap. No self-publishing anymore. He had a book deal and everything. He had real profits from something he wrote. He was finally making a living doing something he loved. And he had Rory's inspiration to thank for that.

Rory's eyes drifted to him in the crowd. He'd felt her presence before like thickened air in his lungs, now the full force of her hit him like a hurricane, ripping the air through his lungs and sending him flying through the air. Outward she looked happy to see him, but her eyes always gave her away, expressing how she truly felt. He saw sadness lurking in their depths. He'd craved those eyes, those lips…all of her, for so long. Being this close to her, he was finally aware of the unlikeliness of it ever happening. He was nothing compared to her. He had written two books, she had written thousands of articles. He was nothing in comparison. A simple sentence, a short paragraph. She was the entire novel, a trilogy, an encyclopedia of everything good and right. Suddenly he felt deflated. She was everything, and he was not. He was simple, and she was not. He'd seen greatness in her long ago – the night of their accident he remembered asking her what she wanted to be, and even then she'd known the exact path she wanted to take, and he'd been so amazed by this brunette, the whole world at her feet, determination in her eyes. He was a delinquent with no hope. She made him feel hopeful.

It's just; I'm in love with him. Despite all the bad he's done, I can't help it; I'm in love with him. The words had fallen from her lips and seared into his brain. Would he ever forget those words? No. Or maybe he remembered them so vividly because of the look on her face: vulnerable and hopeless. So dejected, like she'd given up on happiness. Logan had sucked her into a void she couldn't break free from. She'd been lost when he'd visited her at her Grandparents, and he always blamed Logan for that. He let her veer away from her dreams, her life long ambitions. And Jess had hated him for it. Jess saw her. He'd always seen the greatness she would become, and Logan had let it wither away. Jess knew he would never let her stop following her dreams, no matter how hopeless they seemed – Rory was unique. The whole world was still at her feet, and Jess believed she could do anything. Rory could be anything.

A small smile formed on her lips; a similar smile appeared on Jess. But those eyes, he noticed, remained tainted by sadness, by broken promises and endless regrets, guilt and shame. He felt responsible for it all. He'd let her down, confused her emotions, and made her fall in love alone. He hadn't been there to catch her. He ran, fled. He had been a coward. Regret was all he could feel. He knew he'd damaged her; they'd damaged each other.

He looked away.

Rory noticed the simple changes, the complex changes, his gait, his hardened features, and the slightly muscular build under his suit. His eyes – they remained the same. Tortured as always. Writer's eyes. The eyes that viewed the world in a way only Jess could – the eyes that helped him write about it. She knew there was a wedding underway, she knew she should be paying attention. She'd been waiting for this day since her mother had first fallen for Luke. It was a monumental occasion. One that she would remember for the rest of her life. But…Jess.

The boy she'd once known had evolved into this man. He seemed to be taking her in like a breathe of air after being submerged under water for too long. His eyes though, they seemed to darken. Whatever he saw, he didn't like. What did he see in her, she wondered? Did he see sadness lurking beneath her smile? He'd always known her better then anyone. He'd always been able to tell what she was thinking, like he could read her mind. Could he see the unhappiness?

Rory knew she had a wonderful life, a loving family, and a great job. As a journalist she was accomplished, and she even had an interview with the Stanford Eagle Gazette, which had grown expediently since her internship with Mitchum Huntzberger. Her goal was still working for the New York Times, but in the meantime she wanted to build her resume, gain more experience writing for an actual magazine. And she knew she'd be able to accomplish that. But despite all these great thins she always felt like something was missing. Logan had left a hole in her, one that she'd tried to fill with family, friends, work and even the occasional date…but alas, nothing accomplished a thing. Because she lacked love. And without love she couldn't decide if life was worth it.

Over time the loneliness dulled and she'd managed to ignore it. Now it was pulsating like a festering wound that wouldn't heal. Jess had, for a brief moment, reminded her of what love felt like. Glimpsing him also meant glimpsing the memories they'd shared; good or bad, those memories weren't shrouded with loneliness. Even at their worst, he'd made her feel valued.

Even at her high school graduation when she'd answered his call and he'd stayed silent, a part of her was happy just to hear his breath on the other end. Relieved that despite his disappearance he was somewhere with her on his mind.

Just then she noticed the shift in his expression, the slackening of his smile, and Jess looked away, leaving a hollow ache in the pit of her stomach. They were no longer friends, no longer anything to each other. But his rejection, that moment of disinterest, hurt her still.

Tentative smiles, a brave greeting – "Hello." The first word spoken in over two years. Rory's heart pounded in her chest, hands sweating at her sides as she responded – "Hello." And like that the ice was thawed. As easily as that the tentative smiles bloomed genuine, and the familiar certainty returned to both of them – they were meant to be in each others lives, for better or worse. Whether they were friends, lovers or bitter enemies. The world would always throw them together.

Stay tuned for the next chapter, which will be uploaded next week!

Review and let me know what you think of this chapter.