Author's Note: I didn't intend to write this but it came to me and somehow I ended up typing it up and posting it. It's my first Gilmore Girls fanfiction and is totally and completely AU. I'd also like to take this moment to say thank you to Daygoner (she writes House MD, Maximum Ride and Dark Angel if any of you are interested in that) – I couldn't have written this without her. It is a one-shot and I will not be continuing this story any further. I hope you all enjoy it and PLEASE leave a few words in the form a review at the end – it would mean a lot to me.

Lifelong Regrets

Dedicated to: Daygoner, I couldn't have done this without you!

The cold New York air hit him sharply as he walked down the steps, not sure what his destination was. It was a little after one in the morning and the city was at its busiest. His thoughts turned back to Rory. His Rory. He knew from the moment her saw her that she was his. And she always would be. He smiled, knowing she'd never approve of being anyone's possession – least of all his. But he knew the truth. He knew she needed him, just like his heart ached for her every second of the day.

Some sleep to escape the raw truths of reality but she haunted him wherever he went. Her memory would be forever imprinted into Jess Mariano, into his soul. Waking up in the middle of the night and going for walks was becoming a habit out of need now. The dreams were becoming even more vivid now, even after all these years. He would see her sparkling blue eyes and his heart would sting from the loneliness. From the emptiness he felt without her in his life. He had long since left Stars Hollow; after she left, there was no reason for him to be there. No reason for him to live. But he did. He lived on for her. He lived on, reading her weekly article in the Washington Post. He lived on keeping her memory alive in his heart and soul, for that's where the real Rory Gilmore lived. In him. Now she was Rory DuGrey a highly successful journalist, married to the cunning lawyer himself – Tristan DuGrey. She had left her old life behind for a new, fresh and exhilarating one. Her mother Lorelai was forgotten along with the town she once called home. And yet all its inhabitants continued to praise and love her. Every so often Jess made it a point to go to Stars Hollow to meet Lorelai and his Uncle Luke. He would often stay up and listen to her memories of her daughter.

So caught up in the thoughts of his only love, he didn't see the oncoming car in the alley way he was walking through. The fancy sports car halted before him as his eyes sunk in, not caring whether he lived or died. And just as he looked down to the ground, he saw the flash of blue. The same brilliant blue that shone in his dreams just hours before. It was her! Slowly lifting his eyes, he saw the beautiful orbs looking concernedly towards him, inches from his face. Her manicured fingernail lay gingerly on his chin as she pushed his head upwards. He could feel her shaky breaths on his unshaved skin. Her finger began to tremble ever so slightly,

"Jess?" Her voice was a low whisper. And all he could do was nod in reply. Emotions surged through his body. Anger, resentment, pride but more than anything love. His love glistened through the unshed tears in his eyes and she could see that. She could see that he had never forgotten about her. And her heart began to ache; looking into his eyes, she saw the unrest she had put him through. It was then that she remembered her mother, Lorelai Gilmore. She thought about her every night, but couldn't bring herself to go back to the small town she had grown up in. Her life was with Tristan now and no matter how much she tried, she couldn't give it up. She finally found her challenge and as selfish as it may seem, she couldn't let it go. But now, seeing Jess and remembering her past, she realised that being rich and famous had no meaning if she had no-one to share it with.

Her life with Tristan had long since become dull and monotonous. But that was what they had both chosen. He wanted to be a highly successful attorney, while she wanted to make herself known in the world of journalism and beyond. And they had both gotten what they had wished for. So why then, did she yearn for the old days when she looked at Jess? Why did she feel so anguished when she looked at Jess Mariano with his rugged features, broken eyes and worn down clothes? But she was torn out of her mind's torment by Tristan.

"You're shaking honey. Are you sure you're ok?" He asked, putting his hand on her shoulder. Rory flinched instantly, knowing it was a mistake when she saw his confused eyes. By this time, her back was to Jess and all she wanted to do was turn around and fling herself onto him. But no, she didn't deserve to. He deserved better than who she was. And so, with great pain, she turned around, bracing herself to say goodbye one last time. Yet, when she finally did twist her body, he was no-where to be seen. Where did he go?

"Where did he….? He…. He was just….." Rory stuttered, not being able to form full sentences.

"Who?" Tristan asked.

"The…he…."

"There's no-one here. Why did you even want me to come here?" Tristan asked, still puzzled by his wife's actions.

'To remember. To remember who you used to be.' A voice swept through her before she woke up with a jolt. Her eyes were wide and she groped the bed, trying to find Tristan.

"Tristan!" Her breathing was erratic now and she was sweating profusely.

"I'm here." He said, rocking her in his arms gently. "It was just a bad dream sweetie. Don't worry." He soothed.

'Just a bad dream? You mean the last six years of my life have been a bad dream?' Rory thought.

And on the other side of New York, you could hear Jess Mariano whisper the same things to himself.

Author's Note 2: I hope you all liked reading that! I do, however, have a question for you guys. I noticed that on most Jess/Rory fanfic summaries there was a 'Lit' at the end. If any of you could PM me or leave it in a review explaining what that means it would be greatly appreciated. Thank you! Review!