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Dan’s sophomore year of high school was supposed to be the best of his adolescent life to date: the year he finally started dating Serena van der Woodsen.
Instead it was the year Serena disappeared, the year he lost not only his girlfriend but his two best friends as well, one so slowly he hardly noticed it was happening and the other in one awful, horrifying instant.
It was also the year he first noticed Blair Waldorf, though that hadn't seemed quite so important at the time.
The thing about Chuck is, they all knew what he was like. They knew. Yet somehow, when Jenny sent Dan an S.O.S. text at that party, the first high school party he’d ever agreed to take her to, Chuck hadn’t even crossed his mind. He’d gotten so used to turning a blind eye that if he hadn’t found Chuck on top of Jenny that night he might never have stopped.
Dan gives Chuck a black eye and somehow he’s the one in the wrong. He hates them, all the people he grew up with who so easily write it off, make excuses, let Chuck get away with anything as if "that’s just the way he is," makes it okay. He hates himself for having spent so long doing the same. Even now, he sometimes catches himself thinking of Chuck as the showboating kid who’d made him laugh after he skinned his knee in the second grade.
Before that party, he’d at least tried to pretend that life could go on despite the Serena shaped hole in it. He’d gone out every weekend, sat with his friends at school, performed the minimum social engagement required to maintain his place at the top of the hierarchy. After, he stops bothering. Gossip Girl’s been calling him Lonely Boy since Serena broke his heart and he decides to embrace it. If he’s going to be lonely anyway, he might as well be alone.
He sees Blair Waldorf sitting by herself on the steps of the Met every day on his way to eat lunch in the park and wonders if she's the same.
The thing about Nate is, he loved Serena too. It’s something Dan has always known and pretended he didn’t, sometimes even to himself. He therefore should have known that Nate would be hit hard by Serena’s disappearance, but even before his withdrawal from their social circle Dan was too caught up in his own heartbreak to think about Nate and how he never seemed to look him in the eye anymore. So Dan doesn’t notice and without even meaning to, they drift apart.
Then one day, Dan steps out from where he was hiding from his father’s ongoing house party to find himself right in between Nate and Serena, staring at each other in his hallway. He hasn’t seen Serena in almost a year but it’s Nate’s face that sticks with him once they’re gone. For the first time since she’d left, he’d looked awake.
Somehow, Dan had forgotten what Nate was supposed to look like, hadn’t realized how much he’d faded until the life came rushing back into him. When Serena left, he’d lost Nate too. He can’t believe it took him this long to notice.
It's Nate who comes to him first, sheepish and still not quite meeting his eye. You remember the night she left? The Shepherd wedding? And Dan knew. He’d always known there was something.
Dan’s jealousy of Nate is as old and familiar as their friendship; jealousy of the old money, the legacy, the classic good looks and laid back charm. There was a part of Dan, a part that never quite managed to die no matter how much he denied it, that always believed it would be Nate and Serena in the end. Of course she would eventually choose him.
He lets this all spew out in a St. Jude’s stairwell, the jealousy and heartbreak and loss as Nate stares at him, uncomprehending. And of course Blair Waldorf overhears it all. She always seems to see the worst of him.
He finds Nate sitting on a bench in the park the next day, just as it’s starting to rain. Dan never expected him to hand over his spot as the Dartmouth usher but once Nate’s done it he thinks he should have seen it coming. For as long as he’s known him, Nate’s only ever been selfish once.
Nate tells him he’s sorry. He’d said it before in the midst of a string of excuses - I was drunk, I wasn’t thinking, I never meant to hurt you. Now there’s just one.
“I was in love with her,” he says with a shrug.
And how could Dan fault him for that?
Dan can’t remember a time he wasn’t at least a little bit in love with Serena. He’s not sure who he’d be without it, it’s just a part of him: he’s a writer, he’s a big brother, he’s in love with Serena van der Woodsen. It’s no wonder that he became defined by her absence, Lonely Boy, because with Serena gone, what else could he be?
It started the summer before sophomore year. He and Serena had been hanging out more, just the two of them, no Chuck, no Nate. He was kinda, sorta, with Georgina and Serena had her seemingly endless string of one-week boyfriends, but they were on the edge of something and they both knew it, every interaction heady and weighted.
They were walking along a beach in the Hamptons one night, tipsy and falling into each other, and she’d caught him by the hand and looked at him with an unfamiliar shyness. And then she’d kissed him. Just like that. He remembers fireworks going off over the ocean. His entire life had been building to that moment, even as he couldn’t believe it was actually happening.
Several weeks of sun-drenched summer romance later, they’d sat down before school began and confirmed with all the gravity of first love that this was it, the year their story began. And, as it turned out, the year it ended.
He knows she loved him. She told him so, before and after the fact. But it wasn’t enough. He was losing her long before she left. She’d stay out all night with Georgina and come to school hungover, always choosing parties over dates. He couldn’t see it at the time but after months of combing over every aspect of their relationship for clues to her disappearance it becomes crystal clear. She was getting bored. Simple as that.
Serena's return is just as sudden as her disappearance; one moment she might as well be on the other side of the world, the next her picture's on his phone, her name’s on everyone's lips, and when he steps outside his room, she's right there, in his house, staring at Nate while Nate stares back.
He meets her for a drink and she gives him apologies in the place of answers. She insists she’s different now, that she wants to change, to try. She’d said that back when they’d started dating too and when Nate finally fills in the blanks for him he gets the awful satisfaction of having known better.
But then Serena proves him wrong. She hardly ever goes out, always makes it to school, and in a move that may as well have been specifically designed to baffle him, selects Blair Waldorf as her new best friend. She’s happier and healthier than she’s been in years and even though he knows it shouldn’t, it hurts that she did it by herself. It hurts that he wasn’t enough.
He takes her back because it feels inevitable and breaks up with her once he realizes it’s not. He still loves her. Always has, always will. But the second time around, he finds that’s not enough for him either.
Dan can’t remember the first time he saw Blair Waldorf. He spent years at school with her, probably passing her every day in the halls without even realizing. He knows for a fact he spoke to her once, trying to corral a drunk Serena to safety on Thanksgiving, and he doesn’t even remember that until she mentions it to him a year later. But once he does notice her, he can’t seem to stop.
There’s a stupid essay contest in the spring of sophomore year, one of those academic events the schools like to make a big deal of even though it’s basically just padding for college applications. Blair’s essay is actually good (a rarity) and she’s pretty (not uncommon, but notable all the same), yet he doubts she would have made much of an impression if not for the moment after. Everyone is milling around the entryway, all the contestants being congratulated or critiqued by their parents, except her, a lone figure in a smart navy blue skirt and blazer. She hovers a moment, a feint at waiting for someone, then walks out, alone. He never quite forgets that.
He walks to the park to eat his lunch and passes her sitting on the steps of the Met, a part of the landscape that’s suddenly gained definition. There’s something about the image of her there that strikes him as wonderfully classic, like something out of a movie. He doesn’t know yet how delighted she’d be to hear that. For now, he just sets the thought down on paper, beginning a story he doesn’t know how to end.