Pairing: Rory and Dean
Disclaimer: Everything belongs to Amy Sherman-Palladino and Daniel Palladino.
Timeline: "the party's over" 5.08
Tell me how lonely I look without her. Looking in the mirror, it was all Dean could think. Forty-five minutes ago he had broken up with Rory one more time, one last time, one too many times. He washed his tears away with cold water that made his face feel like it was about to break. Deep down he always knew it would come to this, but a stupid ray of hope kept him trying to bend the destiny that burned him every time he kissed her. She was the love of his life. He had known it since the first moment his brain was asked to form an image of Rory Gilmore so that he could see that she was, in fact, The One.
Breaking up with her was a pain that twisted the very foundations of his soul. To him it looked she didn't hurt as much, that she didn't long for him, that she never loved him at all. How could he see her anymore? How could he pretend he was moving on? He thought about leaving. He thought about it for a few minutes more and it seemed like the best idea.
Dean counted all the money he had and realized there was enough to get away. He had been working overtime, saving to buy an apartment for himself. It was his hope to do this as soon as possible and that maybe Rory would think it a good idea to move in with him. She did have days off from college too. She wasn't always going to be studying or attending parties where rich boys could remind Dean of what he couldn't give her.
But, damn it, there she was, looking every inch of princess without him. Maybe Rory was never meant to last. They were so young when they met and fell in love. She wasn't that girl anymore. He wasn't that boy—they weren't those kids. Now she was surrounded by all kinds of wealth and men and drinks. He didn't belong anymore; it was better to end it quickly than to look at five years of longing for a reason to walk away. This is my reason, he thought when he saw her walking out the door of her grandparent's home. She was smiling at him, apologizing for forgetting and looking as beautiful as she ever looked. He didn't smile back. He couldn't smile back.
"What am I doing here, Rory?" he asked.
"You're picking me up," she answered unaware of his sadness.
In his room, Dean flashed back to this very important moment because in a few seconds she would understand his question, and she would also be very, very sad. Rory would silently beg him to stay, take her out on their date and make love to her for a very, very long time. Like they had been apart for a hundred years—it was their time. He even thought about accepting her quiet request, but he felt too much like a fool. "You look good..." was all good-bye could sound like on a night like that.
Dean started packing everything he could think of: clothes, shoes, money, toothbrush, underwear, toothpaste, soap, books, magazines, and CDs.
To hell with you, Stars Hollow, and your lovely weather. Your stupid festivals and the fake dreams you make me dream. Lindsay doesn't need me anymore. Rory doesn't love me anymore. My family is rightly disappointed in me. Tears were tainting the new shirt he wore for the date – his new jeans reminding him of how naive he had always been about love. How he married Lindsay and broke her heart. How he deserved all of this because he lied to himself about Rory. He lied to Lindsay and pretended to love her after realizing he never had. Tormented by everything he ever did wrong screaming at him, he readjusted his jeans and combed his hair with his shaky fingers. He paced back and forth for an hour making one of Rory's famous pro-con lists in his head.
After a lot of thinking and shivering, after packing everything he could fit into two big bags, Dean finally gathered enough courage to leave in the middle of a very painful night. Before he walked out the door, he heard a noise outside his window.
Outside, Rory gathered her white dress in her arms, trying to climb up the tree by Dean's window. She reached for the stronger looking branches to hold her weight. Rory was breathing fast, and her hair was coming down on her shoulders, when she finally reached over to knock on the glass.