Disclaimer: I do not own Gilmore Girls. I do own this fic. While its not necessarily an AU, its still my take on the GG, so characters and events from the original show will have just a little bit of my own spin. No regurgitation of the same old story.

Note: Why a Rory/Jess fic? I always felt that the character of Jess was one of the most well-written and entertaining characters on the show. It also helped that Milo Ventimiglia is so hot. Anyway, I loved how Jess always seemed to show up and mess up Rory's life at just the right time. I kinda always hoped they'd end up together, but…

Oh, and sorry if this first chapter is boring. I just felt like there should be some sort of introduction.

Kudos to Amy Sherman-Palladino and Queen

Chapter 1—I Want To Break Free


I've fallen in love / I've fallen in love for the first time / And this time I know it's for real… I can't get over the way you love me like you do / But I have to be sure / When I walk out that door … Oh how I want to break free

She should have known better. Was she seriously that naïve to think that he was out of her life forever? No. He was like a weed. She would cut him down, destroy him, remove all traces of his presence and then turn around to see he had taken root in her life once more.

Of course, he did have a strong hold in her life simply because his uncle was dating her mom. Rory had known deep down all her life that Luke loved her mother. A part of her had always resisted that truth, because as a child Rory had wanted the complete family portrait. She had wanted Christopher to be more like a father figure and less like a sperm donor. And she had wanted her mother to have her happily ever after.

As she had grown up, though, it had become obvious that Lorelai's fairy tail prince wore flannel and a baseball cap, and was eternally flipping burgers and refilling coffee mugs. It was not glamorous, but it was real. And the Gilmore Girls needed reality every once in a while. Luke was the only one that could make Rory's mother happy.

But with Luke came his crazy family. April, Rory could handle. Liz and T.J.—well, they were annoying but lovable at the same time. No, for Rory the problem was Jess.

Rory had never figured Jess out, but he knew her. He knew her desires, her fears, where she was ticklish, what made her cry, laugh, scream…Jess knew her better than she knew herself.

And, blasphemous though it may be, Jess knew Rory better than Lorelai.

And Jess would not go away.

Funny, to think that the boy who ran away to California, never said goodbye, and broke Rory's heart, always seemed to find his way back to her. First, he had come back to tell her he loved her. The next time he showed up, he wanted her to run away with him to New York. Rory could still see him standing there in her dorm room at Yale, begging her to say yes. Part of her did. Part of Rory wanted nothing more than to run to New York with Jess. She would have lived in a cardboard box in an alley for him. She had just wanted to be with him, wherever that might have been.

But Rory was not programmed that way. Her rational, methodical brain had quickly presented her the cold facts, and she had reasoned how the cons far outweighed the pros, at least in quantity. Rory chose Yale and said no.

But Jess continued to be in her life.

She still squirmed at the memory of Jess and Logan's meeting. She remembered the lecture Jess had given her, calling her out on Logan and dropping out of Yale. And she couldn't fight back because she knew that everything he said was the truth. But even though she knew Jess was right, she stayed with Logan. Oh, she changed a few things. She moved out of Emily's mansion and went back to Yale. But she continued to date Logan, despite his many transgressions.

When Logan's flaws became too much to bear, Rory had run not to the bitter streets of New York City, but to Philadelphia where a strange yet appealing Jess had greeted her with open arms.

He was finally ready, and had assumed she was too, but Rory had felt out of place the second she entered the publishing house and saw Jess. He was overwhelming confident, no longer James Dean but Cary Grant—grown up, mature, and experienced.

The boy was a man, but Rory was still a little girl playing pretend. She couldn't do that to Jess. She said she loved Logan, and even now she knew that had been true, but she had loved Jess more. She had loved him enough to stop him from hurting again.

Rory went once more back to Yale. She graduated, and in a moment of clarity broke up with Logan. She had landed her first "real" job following Obama on the campaign trail. She entered the real world and discovered its joys, pains, and sorrows. Rory Gilmore moved further away from Stars Hollow and her childhood.

But Jess always seemed to pull her back.