Title: I Am Trying to Break Your Heart

Disclaimer: I do not own Gilmore Girls, the characters, or the WB. And if I did would I be here writing fan fiction? ;)

Dedication: To Ari, Elise, Ilona, and Lee for reading over this and making such wonderful suggestions and pointing things out I would've never noticed. Thank you for being so helpful, specific and supportive.

And to everyone else at the Lit Thread at S-H.org just because they're awesome.  I love you guys.

A/N: Title comes from the amazing Wilco's I Am Trying to Break Your Heart. I highly recommend them, btw. All chapter titles come from the last line of every new verse.

Please R&R.

Part One: What was I thinking when I let go of you

          The yellow light from the apartment across from him has gone out.

          He blows out a wisp of smoke, holding his own burning cigarette. He follows his old routine, and stubs the cigarette against the concrete, liking the sound of the fire against the cold floor. He takes a minute to look up at the monstrous black sky, hovering over the big city, daring them, before he reaches for another cigarette.

          His fourth.

          That fact does not go unnoticed by him.

          Every night he waits until the small hand hits exactly at the eleven, and the big hand at the nine. At that time, he heads out to his balcony and fits his legs tightly between the concrete and the rusty green railing. By the end of his third cigarette, the lonely old man, directly across from him will turn out his lights. He thinks it might be his future.

          As soon as the fourth cigarette is lit between his fingers, out escapes a bitter, low laugh. He shakes his head once, smokes his cigarette and stares down at the depressing noise of the city. Every night he waits. That was what it was all about, wasn't it? He waits to hear specific sounds, down below. He crosses them off in his head as they are heard. Sometimes, he will deny sleep, staying up until dawn, simply for the sound of a beer bottle being thrown harshly to the ground. As soon as he hears the loud crash, he pictures the broken glass scattered in the street, skidding across, becoming scarred. Then, it is okay to go to sleep.

          Everything must be crossed off his list. He finds that he can't sleep without knowing that his list is marked from top to bottom, nothing left out.

          It is a routine. It has to be completed in a full circle.

          The rest of New York City go through their own routines. Some wake up, kiss their loved ones goodbye, go to work, come home, kiss their loved ones goodnight. Others had simpler routines to follow. They were difficult to break, he had learned. And while others kept their routines for security, his helped him to ignore the growing emptiness in his tired body.

          Like all of them, he went around in a dull circle, never daring to break it. He won't risk it.

          But tonight, under the clear, pitch-black sky, with the slow, thin wind blowing at his side, the chain had broken accidentally. During his fourth cigarette. His mind unconsciously wandered off. Drifted back.

          Once routines are broken, you never go back. You start over again. But in his case, with his already destroyed, he went along, going with the flow. From his exterior, he holds the same lifeless character. His back takes its hunch-back form and his legs hang dully above the streets. His cigarette glows between his middle and index fingers. Inside, sparks set off in his head, soon spreading throughout his body.

          And for the first time in three years, he feels alive.

          A blurry picture of a girl begins to form in his mind. He closes his eyes, thinking that maybe it will become clearer. To his surprise, it does. He can see the lines of her face, the curves of her lips, fitted into a small smile. The soft brown hair coming down past her shoulders; her blue eyes sparkle, blinding all that meet them. A sharp pain slides in his chest.

          The image is fading away, morphing into another. Now, she is running in the sand, barefoot, with her hair pinned up, a loose strand hanging from the side of her face, flying as she goes along. Her hands hold the long, white skirt of her dress, saving it from ruin. And she is smiling. Her eyes are gleaming and her smiling matches it well. He can't tell what kind of smile it is; he can't fit it in any category.

          He would like to think it genuine, but the bitter side of him knows the ruthless smile.

          His eyes shoot open, startled by the prick of heat between his fingers. He stubs it against the ground and doesn't find the sound so satisfying all of sudden. He leaves it to burn out as he reaches for a fifth cigarette.

          There has never been a fifth.

          He takes his first taste of a fifth cigarette and discovers that he loves it.

          But it all turns bitter when he blows out the cloud of smoke.

          He thinks of the fourth and her running across the sand, the smile on her face. And then comes the third and the second and then the first. The same feeling being repeated over and over again, just building up every time. It all began with the first. It was those first five little words that started every mess he had ever made. Including his routine.

          "What are you doing here?"