Author's note: This is a piece I wrote awhile ago. I had toyed with idea of evolving it into a full length piece but I never got around to elaborating on it so it simply remained a stand alone. The following is simply my interpretation of Dan's thoughts, set sometime around 'The Kids Stay In The Picture.' Thank you for reading :)
It's as he takes a seat in the uncomfortable chair that encourages him to keep his back straight and his mind alert that Dan Humphrey allows himself a moment to accept the revelation that had unfolded and was dismissed all within short succession. The contrasting scenes flash behind his eyes with clarity. Eric, astounded, but amused, assessing his idle comment with secure confidence and a nonchalance that Dan himself took great efforts to assume in his regard of the subject is what he pictures first. He recalls the way that Eric suppressed his laughter, with a smile that gave it away, but assessed the situation with a maturity well beyond his years.
Eric, always the spectator to the incessant drama that was constantly unfolding in their lives was an underrated mind among them, Dan thought. He was not cunning or deceiving, he was simply an observer. He offered fresh perspective, and having been the observer amongst it all, Dan took him seriously, because Eric knew things that he didn't, had insight that barely anyone ever chose to acknowledge.
He remembers the conclusion that Eric had drawn and Dan had silently deemed true enough, perhaps with a side of dread, because really, what could become of this?
His second recollection is dedicated to his denial. There he is, standing less than a meter away from her. She had defended him, to Chuck no less, maybe not for his sake instead of for her own, but defended him nonetheless. Despite this fact, he attempts to make it clear that the kiss meant to him what it meant to her, nothing. Then in turn they each take the opportunity to assure one another that the right one is out there. Blair speaks of Serena when she addresses Dan's prospective future but when he turns to look at her he accepts fully that Eric's drawn conclusion has cancelled out the lingering feelings he had wrapped up in his adolescent ideal.
He realizes its nostalgia that always brings him back to Serena. It's when he's alone, and not distracted with the potential of someone new that she comes to mind. It's the fact that she was his literary muse for so many years that he falls back on her. It's all in the fact that she had been what he had aspired to mean something to for so long and that through every up and down of their tumultuous relationship he continued to hold out hope.
Maybe he's naïve, because he acknowledges that Serena is flighty and moves on quickly. She falls in love fast, or perhaps it is simply that she doesn't fall in love at all. She moves from him to Nate, to someone new, and then back to one of either of them. Of the two Dan knows that Nate is probably better suited to her, but this could be simply because he's finally come to realize that out of Serena and Blair, Blair is more what he would consider to be his type.
Blair is still deceitful and she still maintains her elitist attitude but there's a certain inflection in her tone when she demeans him that he recognizes to be friendly; its subtle, but it's there. The dynamic of their relationship is based on the fact that they both maintain the same regard to one another that they always have. She is Manhattan and Dan is Brooklyn. They are opposites, opposites with more in common than either of them would care to admit. Blair is well read, she is witty, she is determined, and she works hard. She strives to attain her goals based on her own merits.
In retrospect Dan had noticed it was not out of her strive for perfection that she worked so hard, but that she worked so hard to prove that she deserved what she had. While Serena had always had the fortune of things falling conveniently in her lap, Blair had always worked for what she wanted.
Taking this into consideration Dan concedes that this alone warrants some of her dramatics throughout high school. His failure to ever scratch the surface of her is what had been the misgiving between them. If he had known before what he knew about her now Dan knows that things would be vastly different. Evidently, understanding goes a long way. He grants that Blair has always been more clued in about him on a baser level than he would have thought, and certainly more so than he had ever been about her. The Blair he knew in high school was a misconception; the Dan she had known was merely a personality type and not a fully fledged person.
Washing his hands over his face with a gruff sigh pushing past his lips he looks at the blank word document that glares at him from the screen of his laptop. This is where he normally would have woven a tale that mentioned no names but was clearly all about Serena. Instead he stares blankly at his page and thinks that it would be entirely too cliché to begin writing about a boy from Brooklyn and a girl from Manhattan that he certainly doesn't stand a chance with. After all, this is what the first tales involving Serena had entailed, and Dan had hated himself then for writing something so self indulgent. On top of that, the idea of his relationship with Serena and his (non) relationship with Blair paralleling on any sort of level beyond the obvious is something he would prefer to avoid.
He and Serena are on again off again. He and Blair, he accepts, are constantly off.