Note: My first real attempt. Hopefully this will be multi-chaptered. There will be more DB coming up, but the whole story (with the possible exception of the ending) will be told from Serena's perspective. I am sure this is riddled with mistakes and flaws, and I will always welcome constructive criticism.
Serena van der Woodsen was not an insecure person. She could be a flaky person, a selfish person, and even on occasion, a manipulative person, but Serena was not an insecure person. Why should she be? She was beautiful, charismatic, and fabulously wealthy. She had friends who supported her, a family that loved her, and fans who adored her. She was very aware she lived a life that most could only dare to dream of, but she tried, though rarely succeeded, to not let herself be defined by her social status as the Upper East Side's "golden it girl. She knew she could have whatever she wanted in life, well almost anything, but she almost destroyed the happiness of the two most important people in her life because she felt that their their mutual affection meant she was no longer needed in their lives. She was afraid that she would become irrelevant, and that was not a feeling that Serena van der Woodsen was use to.
XOXO
Serena knew her relationship with Dan would never be what it once was. Daniel Humphrey had come into her life and changed things for her. He helped show her what it was to be liked for who you are and not who you know. He helped her realize that she was a lot more than just a dazzling smile and golden hair. She had loved him as much as she knew how, and at one point they were happy, so very happy. Of course, everything wasn't perfect; they, like everyone, had their issues. She had bad habit of concealing the truth from him and he was known to be a little self-righteous. She lied because he judged, he judged because she lied. They continued trying to make their relationship work, but they found themselves falling into the same pattern of destruction over and over. Eventually, the final blow was struck. The marriage of her mother to his father and the discovery of a long lost lovechild. Unrealistic expectations and shadowy pasts could be worked on and forgotten, but a shared sibling was hard to overcome.
XOXO
Still, they tried to make whatever it was between them, work, but while Dan began to mature and let his judgements fall to the side, Serena had a harder time being able to focus all her attention on him for an extended period of time. She didn't mean to be cruel, but she was a person of joy and desire, so she tended to live her life for whatever was giving her the most joy at a time. She didn't know when she began treating Dan less as her first love and more as her security blanket, and there was never malice in her actions, but, as she later learned, she did inflict pain. Every time she used him as a safety net, their bond became a little weaker, a little more frayed, and a little less secure. Even when she discovered that all his attention was no longer focused on her, she worried little. Serena trusted that Dan would always see her as his golden icon, his dream girl, his muse, but by time she decided to give their relationship all of her effort and concentration, she discovered that he had a new muse.
XOXO
He had had other girlfriends in the past, and Serena had not cared. He had claimed to be in love with another girl, but Serena had not worried. The first time Serena ever began to question his undying devotion to her, was when she discovered he had been keeping his new friendship a secret from her. If they were only friends, then why the need for lies? He claimed embarrassment of the connection and once again, declared that it was only a friendship. Under normal circumstances, Serena would have taken his word and gone back to her blissful entitlement of his love, but this time felt different to her. She was never the most observant person, but this time, she felt like something big had happened, and she still unaware of it. A change had occurred in Dan, and yet, she couldn't quite place it, but eventually, she grew tired of trying to unravel his mystery, and she ignored it. When she looks back at those moments, she is annoyed with herself for not seeing and understanding what was standing right in front her. Maybe, if she had paid more attention, and cared just a little more, then she would have seen it, and possibly even have stopped it. Though in her deepest heart, she knows she couldn't have stopped it because while she was off playing in other gardens, Dan had began writing a new story, and she was no longer the star. When Serena looks back at that night, she realizes that she should have known what was to come. After all, Dan Humphrey and Blair Waldorf kissing was not just another ordinary day.
XOXO
Note 2: I hope you liked it!