Lorelai Leigh Gilmore had done something wrong and everyone knew it. But to her, it had not been wrong, at least not in the way most people would think. And even though the people around her all thought she had made the biggest mistake of her life, including her closest friends and especially her mom, what they could never understand was she had consciously chosen to sleep with Dean. She continually regretted the fact that it had hurt Lindsey, and she would never be able to justify that or feel any worse over Lindsey than she already did.
As harsh as those consequences were though, the real truth was that what she and Dean had done had not been about Lindsey; it had been about them. It had been about their past and their recognition of missed chances, and it had been about finally acknowledging that as beautiful as first love was, she and Dean were fundamentally not meant to be. In some ways, they both knew that taking this step was also bringing them that much closer to an end. They had both tried to deny it until they couldn't any longer, which was made all the more apparent tonight, the night of her grandparents' alumni party.
Dressed up in a dress that she would never wear again, her grandmother's tiara perched perilously above her head, along with a stash of jewelry that could rival the Crown's jewels, against all odds, Rory discovered that she had actually been enjoying herself. Of course, it could also have been attributed to the particular entertainment of the evening. She smiled to herself as she remembered Logan and Finn bribing the waiter to keep their drinks filled, talking in circles over the poor guy's head while Colin had stood nearby, amused by their never-ending antics.
Rory gazed at her reflection thoughtfully as she carefully took out the numerous pins Maria had stabbed into her hair, and couldn't suppress a sigh as she thought of Dean. She could still remember his face as he spoke those parting words: "I don't belong here, Rory. I never will, and I don't know if I would want to." At that moment, shame had filled up in her, her inner voice telling her that she should have been the brave one, that she should have been the one to have spoken up sooner. Instead, she had let the burden fall to him. She was sad that their relationship had at last played out its course, but she was also relieved at the same time. As she slipped into her nightgown, rather than pondering or torturing herself over the things that might have been, Rory lay in her bed asleep, comforted in the knowledge that she would no longer be standing still in her life.