November 7th, 2012.
It was anniversary of arguably the best thing to ever happen to Chuck and Blair.
It was the dawning of a new era, a changed perspective on everything they once knew, and the beginning of a journey they had never imagined they would take.
For Blair, she had once in her life done something that she didn't have to manipulate or scheme to perfect. It had been building all day for her. There had been so many signs from the people around her and the world, that she hadn't realised were there until many years of contemplation of that night and its lead up.
She recalled Serena telling her, "Sometimes talking about it, or planning it can ruin a good thing." It wasn't on a bed. It wasn't with her boyfriend. It wasn't planned. Blair had put absolutely no effort or hard work into making sure it happened. It was just natural. He had come to her naturally like a moth to a flame without her having to do anything but be herself and relax. And it was the best night of her life. Perhaps that was partly what made her so afraid and reluctant of Chuck at first. Because since when did Blair Waldorf get something so amazing that she didn't have to work for or plan? It was out of her control.
Another change for Blair was the revealing of a new side to her personality, and simultaneously saving her from a life of society smiles and a stiflingly perfect-on-paper relationship with Nate. Her outfit prior to arriving at Victrola said it all, with the uptight neckline, long sleeves and the mandatory symbol of the restrained society woman: her perfectly placed headband on her flawless curls. When it came off later that night, she had her chance to show the world for a night that she could be so much more. More passionate, alive, fun and genuinely happy. All thoughts of Nate, her mother and the world's expectations of her flew away. This was all at the hand of a dare by Chuck Bass.
For Chuck, it had been a day of unexpected accomplishments. A day where he had somehow managed to man up, if only for a moment, and please his father with something he had done. A rare moment where Chuck actually felt peaceful and happy, like maybe he wasn't a low-life and maybe there was a mature part inside of him that just needed the right person to bring it out. And when he had fallen in love with Blair on that stage, something had shifted within him completely, pushing the thought of even Bart to the back of his mind. He offered her a gentlemanly ride home in his limo. Interestingly enough, earlier that day, Dan (while being caught making out with Serena in public) had said to Serena, "That's the plight of the Manhattan teenager, no cars." Well Chuck and Blair unknowingly found the solution to that issue.
When Blair had leaned over across that limo and kissed him, his face was filled with fear and uncertainty despite the need inside him, because this was way more than he expected to happen that night. He already got his father's approval which was wondrous enough. But for Blair Waldorf, his best friend's ex who he just realised he was in love with, to be deigning to throw herself at him? He had once said to her that he would be honoured to be playing even a small role in her deflowering. What on earth was the universe doing to him? He had to ask if she was sure. When he thought back to that night years later, he had also realised that it was the only time he had asked for a girl's consent. He, Chuck Bass, was almost shy, and a complete gentleman about it. It was difficult for any of his future moments of maturity to equate to his first.
It was beautiful act of fate that their paths should meet the moment that they both had already taken leaps in their separate lives regarding Nate and Bart. It was a stolen moment that defined all that the future Chuck Bass and Blair Waldorf could be. It was a night where the both of them dared to take a chance at freedom, peace, maturity, companionship, happiness and love. Their journey from that moment on, whether they knew it or not, was one driven by the need to finally have all of those things that were dreamt of on that special night.