Chuck's problem was always the same. He couldn't understand what Blair saw in him. She had told him a few times now that she loved him. He knew she believed it; it's just that he knew it wasn't really true. She was more honest at the beginning, before she ever loved him. She was as honest then as the other women he'd had. They all wanted something from him. Money, sex, drugs a good time, all those things he understood. But Blair had changed, now she wanted more. He wasn't sure when that happened.
In the beginning, Blair only seemed to want what he could offer her in bed. She wanted to keep him her dirty little secret. As much as he didn't want to lose his best friend because he was with Blair, he could never shake that feeling that Blair knew he wasn't good enough for her. Not in the public eye any way. That was the story of Chuck's life though. A mother who died giving birth to him…really the ultimate rejection; a father that didn't have a moment in time to spend on him unless it was to tell him what a disappointment he was. So when Blair had wanted to keep them a secret, part of him understood, embraced it, accepted it as his fate. He accepted it, until she took Nate back. While he was upstairs lying in her bed, her lips still bruised by his kisses, she agreed to be seen in public with Nate. Chuck could still remember the rage and hurt and helplessness he felt in that moment.
Again someone else came before him; again his emotions and feelings were not even considered. Again he was nothing, not even a footnote in the fairy tale story about the princess and her knight in shining armour. No one ever writes about the evil prince that the princess sleeps with, they always write about the knight. So, if that was the role he was meant to play, the secret lover, jilted and cast off when something better came along, he wasn't having it. He was Chuck Bass. This was his story, his dark princess and he had just had to make her see that.
He managed that alright. Sure, she saw him, realized he was a dark prince and then walked away from him. Not without telling him first that he could never be what she needed. Chuck still remembers how badly that truth hurt. He had fled the country to try and get away from the reality of it. From that and something that felt like heartbreak.
But he didn't stay away. He never could. Blair was like his own epicentre. For years they did this dance; the one where for a while he fooled himself into believing that he could be good for her. That because he loved all aspects of her and understood her better than anyone that he could make her happy and then reality would hit. He would recognize how terrible for her he was. That the only times she was happy with him was when she thought he had changed; that he was a better man. This is was time of the dance where everything spun around, where he would do something stupid, something real and she would remember that he was not worthy of her, of her love. Then they would end things.
At the center of it all though, Chuck knew. He just knew he wasn't good enough for her. He knew that she could never really love him. No one ever did. Not once they really got to know him. And Blair? Well she knew him really well. Chuck knew that Blair had it right in the beginning, when she wouldn't date him. When she used him like everyone else. When she knew that he wasn't fit to be loved by her.