A/N 1: Hello lovely readers! This is my first Gilmore Girls fic, so I'm extremely nervous about posting this. I'm not too sure that this is going to be a typical one since I'm trying out different writing styles for college right now, so bare with me. Review, favorite, and follow if you enjoy it! (P.S. Please be nice. I know I'm not the best writer in the world and this is my story, so…)

She ran down the empty streets of her hometown in the middle of the night. It felt as if she was going insane, like there was no shred of hope left in the world. Everything had been ruined and there was no way for her to fix it. She came to a screeching halt once she reached the bottom step of the gazebo and inhaled sharply to catch her breath. There were times that she had done this before, in the past, when things were much simpler and she didn't have a thousand things running through her mind. The ice cold breeze and light rain hit her face and it would have been welcomed, but her eyes started to water involuntarily. Before she knew it, she was clutching the railing for dear life feeling like she was going to fall to pieces on the ground for everyone to see if she even dared to let her hand slip.

Lucky enough for the brunette, everyone in the town had their lights out and were hopefully in bed fast asleep. By now, she thought, someone would have noticed her dashing through the streets like a mad woman. She almost hoped that a concerned voice would open their window and ask if she needed any help, but it was better off if that didn't happen.

Finally, after moments of gasping for air, the girl sat own and held her face in her hands. The winter air had made the large ring on her left hand colder than ice, but yet it seemed to burn the skin on her bare cheek. She shook her head in a slow and painful manner, trying to figure out how she even got to this particular moment in time. If she could, she would rewind the past few years in hopes of trying to pinpoint the moment where things went wrong. Pinpoint the exact millisecond where she felt like she had officially lost it. Pinpoint why on earth she was even in Stars Hollow at this time of night. She had a beautiful blond man waiting for her at home, three and a half hours away from her. The girl laughed at her own thought and felt as if she were truly insane. "Get yourself together, you idiot," she spoke softly to herself, trying to soothe her own nerves. "What is wrong with you?" She asked quietly to herself as the tears poured down her face. There was no holding back any longer. This is how things were. She was sad, drunk, and nothing in the world seemed to matter anymore.

It was in the midst of her tears when everything went completely silent and still around her. This had happened a few times before, but it was like time had stopped and she almost wanted it to stay that way. If it had, everything would eventually feel better and she wouldn't have to be the way she was. Oh, she was supposed to have the world in her hands and she almost had it. Her grip wasn't tight enough and she let it fall and shatter to pieces at her feet. Still, she cursed herself for ever letting that happen.

"Rory?" A confused voice yelled from across the street. The girl didn't look up, but instead prayed that she would turn invisible. Who in their right mind would be awake at this time of night? She knew that Stars Hollow went dead as soon as it hit one o'clock. This was supposed to be her escape and some jerk had to go and ruin it for her. "Rory." The voice inched closer, but it still sounded tunnel-like. She hoped that she was hearing things, until a warm hand touched her shoulder. As she lifted up her head, the first thing she noticed was the mascara that had stained her palms and pictured just how messy her face looked. Slowly, she looked up, hoping that it was only Kirk and that he would eventually go away, but no, that's not how the world works. Everything had to be the opposite of what she wanted.

Their eyes locked for the first time since he yelled at her outside of a bar in New Haven. Icy blue to chestnut brown. "Get away from me," she spoke through gritted teeth. "Go!" Her voice was louder than she had intended it to be. She was waiting for an old lady to abruptly shout down to the streets, telling her to shut up and go home.

He sighed, "What is wrong with you?" He rubbed the back of his neck, a move she had seen him do a dozen times in the past decade or so.

She stood up to his height and hastily flattened her dress with her hands. "You shouldn't be here, Jess."

"What, and you should?" He crossed his arms and scoffed, not knowing what he ever did to make her angry or even slightly upset. "I cannot believe that I've been here more often than golden girl Rory Gilmore. It seems like a miracle that you're even standing in the middle of this godforsaken town."

Jess' words cut her deep inside, feeling those words wounding her in the worst way possible. It may have been the truth, but it didn't mean she wanted to hear them spit out at her, especially coming from Jess Mariano. How was it that Jess, of all people, seemed to have himself more put together more than she did? "Why is it that when I ask you to go away you decide to stay and pry?" Rory started to walk away, not wanting to hear his response. She knew it would be a smart-ass comment or even the truth. She wasn't even sure which one would've been worse. The girl picked up her pace, making sure that he wouldn't catch up. She felt the wind in her hair eventually as she ran down the familiar streets, but low and behold, Jess caught up with her, grabbing her by her elbow and making her stand still.

"Stop running," he hissed. "God, haven't we been through this exact scenario before?" He cracked his trademark crooked smile her way which didn't seem very amusing at the moment.

"I wouldn't remember," she lied, trying to wound Jess as bad as he did her, but she had always been a terrible liar and that's just one of the thousand other things that he remembered about her.

He tried to move closer, but went as slow as possible, trying his best not to scare her off. Once he was at a reasonable distance, he smelt the wine that she had been drinking beforehand. "Huh, that definitely explains the attitude."

"Why don't you just leave me alone?"

He didn't listen. He never listened. Instead, he grabbed ahold of her wrist and started walking towards the diner. To Jess, she felt like a dog yanking at its leash, trying its best to get out of the hold that it was in. He tried to be gentle and friendly, but she wasn't letting it happen. As soon as they came up to Luke's, he took his keys out of his pocket and unlocked the door. This sight surprised Rory. "Why do you have a key?" She had suddenly dropped the angry tone she had been using before and instead sounded like a confused child.

"It's kind of insignificant at this point, don't you think?" The door opened and Jess tried to pull Rory inside. Taking a chair down at what used to be her favorite table, he made her sit down as he trailed behind the counter to start up the coffee machine. Not only was it her favorite thing in existence, but it would also help to sober her up.

"Why do you have a key?" She repeated herself as she set her arms on the table and laid her head on them.

Jess shot his head in her direction. "You miss out on a lot of small things when you leave a place for five years."

A/N 2: So, sadly, we're going to pretend that my favorite scene in 6x16 didn't happen and the last time Jess was around was 6x08. Also, to keep things interesting, I thought it would be awesome to make a playlist for this fic. I'll be updating it every now and then, but here it is (luna-ofrps . tumblr jessxrory) so you have a little glimpse into the future. Please, do not kill me.