It happens like this.

Dan is standing on the edge of the sidewalk with a bubbly (and clearly drunk) rich girl's arm grasped firmly in his hand. Thoughts spin off in all directions, disbelief that he's actually touching Serena van der Woodsen, regret that he didn't have the coordination to save the pie he came all the way to Manhattan to get, and wonder that she's so intoxicated she doesn't even realize that taxi almost cut her down.

He lets go the second her friend comes into the picture, one he knows in name and reputation only, and steps back as Blair grabs Serena by the shoulders and doesn't seem to notice him standing there.

"Can't let you out of my sight for two seconds can I?" she asks tiredly.

Dan stands awkwardly for a few seconds, unsure if he should say something or just leave when "she almost got hit" fumbles out of his mouth, gesturing wildly at Serena, the street, and the remains of his dessert flattened on the asphalt.

Blair looks at him, brow arched all the way upward, and he's just waiting for the sarcastic remark to come.

"Well aren't you the knight in shining armor?"

Not exactly scathing.

/\/\/\

It happens like this.

One day Serena is the Upper East Side's queen of everything, and the next she pulls a disappearing act any magician would envy. No one, not even that damn website, has any idea why or where she could have gone.

Dan walks idly along the sidewalk two days after she vanishes; backpack casually slung over one shoulder, sipping hot tea as he passes the Met steps.

"Hey, pie guy!"

At first he doesn't think the comment is directed at him, oddly random and unclear, he keeps walking until he hears it again. Stopping to look around, he spots Blair Waldorf sitting at the top looking down at him with a bemused smirk on her face.

He's still not sure she was talking to him, going so far as to point at himself causing an exasperated sigh and a come hither gesture that instantly makes him nervous.

"Pie guy?" he asks when standing directly in front of her.

"Well I don't know your name," she replies, patting an open spot on the concrete. "But I seem to recall a pie involved in our last meeting."

"Oh," still confused, "I guess there was."

"Have you got a name? Or am I actually going have to call you Pie Guy?"

"Dan," he says offering a hand. "Humphrey."

"Blair Waldorf," she replies shaking it limply.

"Yeah, I know."

Her face lights up.

"Of course you do."

/\/\/\

It happens like this.

Dan is sitting on the couch about to waste away another Friday watching Nick at Nite when his phone vibrates on the table. He lets it ring a few times knowing no one besides his parents ever call him, or Vanessa, but she's been gone for almost a month now.

When he does pick it up Blair's name is flashing on the screen, causing him sit up quickly, mumbling "uh, hello?"

"Never keep a lady waiting on the phone Humphrey," her voice carries over the receiver.

"I didn't realize," he replies, a slow grin forming on his face. "I don't get a lot of calls."

"Hardly surprising living in Brooklyn as you do," she shoots back.

Forty-five minutes later he's climbing into the back of a limo, a drink immediately placed in his hand, and he looks to see there are three other girls inside all looking at him with a snobbish curiosity.

He sits back next to Blair, the martini glass cool in his hand, trying his best not to look uncomfortable. Introductions are made, her voice clear and firm as she names her court and it doesn't take a genius to realize she is indeed the new queen.

What he doesn't get is how he fits into all of this.

"Don't like your drink?" Blair asks, nodding at the still full glass.

He takes a pull without thinking, makes a face and nearly chokes causing everyone to laugh.

Blair pats his knee and smiles only at him.

"I have so much to teach you," she says in all seriousness.

He has never heard more frightening words.

/\/\/\

It happens like this.

Dan is sitting next to Blair at her usual picnic table during lunch, blissfully by themselves because her little followers are off on an errand he's not privy to. She's idly flipping through the pages of his current book, Faulkner, while he quietly eats a sandwich.

They're not so much a spectacle anymore, the student body having gotten used to the sight, no more daily blasts about Queen B and her adopted Brooklynite. There are still the rumors though, that she's simply slumming it while managing to keep Nate Archibald for the limelight, but they're readily ignored by all parties involved.

He does think it a little odd that Nate is never around when he and Blair are hanging out, or the fact that they've never officially met, but usually files it under not a problem.

"I'm bored," she says suddenly.

"Is lunch usually a big source of entertainment for you?" He replies, wiping the crumbs from his sandwich away on his pants. Something she notices and knits her brows together at.

"You're such a heathen sometimes."

"One step above beating my chest and grunting."

She doesn't laugh, but shakes her head, and he knows his humor gets to her in its own way.

Standing up suddenly and grabbing her bag, she beckons him to follow.

Thirty minutes later he's standing in a Brooks Brother's dressing room trying on suits while Blair waits patiently to appraise him. Slipping on a pair of gray slacks he wonders just how he got talked into this. Worrying that saying no to her (cutting class and playing dress up?) is becoming a more difficult task the longer she stays around.

Putting on a crisp shirt and tie, always a must, he walks out into the viewing area. She already loves it, he can tell, those Bettie Davis eyes giving him the once over before lighting up with approval.

Catching sight of himself in the mirror he has to admit it's not half-bad, kind of a Sinatra early Rat Pack thing going on.

Still, when she starts going on that if he only dressed this way more often dating wouldn't be completely out of the question for him, he argues against her because no matter how good he looks he refuses to be her Ken doll.

/\/\/\

It happens like this.

Dan knows Blair has her faults. She can be incredibly selfish, mean, and the little games she plays all the time, the manipulation, leaves him worrying she might a bit of a sociopath.

Still, no matter what she does or who she screws with, he is always off limits in that regard. And no matter how many times she calls him, how much time they spend together, there's still a worry that he's just some sort social experiment. One she'll eventually tire of.

So when she shows up after a cryptic text message, I need to talk to you, he begins to suspect his doubts might have been for naught.

First thing, she came to Brooklyn willingly, just to see him. Second thing, she didn't go to Nate, you know her boyfriend for whatever it is she needs to talk about. Third thing, she doesn't even wait to be invited in before she's wrapping her arms around him and pressing her cheek against his chest.

He doesn't ask at first, merely rubs her back gently and squeezes assurance that he's here for her.

It takes five minutes and half a box of tissues to get it out of her. Her dad left her mom and ran off with a model. A male model. Dan can't begin to imagine how to sympathize, it sounding like to kind of thing that only happens on TV, merely trying his best by putting an arm around her shoulder.

Hours later, when she's voiced every single doubt in her life ranging from suspecting something about her father, to always coming in second to Serena, and the pitfalls of being queen, they sit on the couch in silence watching some old movie on AMC.

She's come to trust him, he figures, all the things they talked about are subjects she clearly never shares with others. So he finally has the courage to ask why him, now and for the few short months they've been friends.

Staring long enough to make him shift in his seat, she scoots a bit closer and rests her head on his shoulder.

"I needed someone who would care," she says quietly.

His heart tries its best not to break.

/\/\/\

It happens like this.

Blair throws a party and attendance is mandatory. She even invited Jenny, which resulted in a week of hell with her constantly badgering him to tell everything he knows about UES parties, her desire to be accepted by them a cause for great worry.

He stands off to the side in his Sinatra suit, watching as Blair plays hostess, a role she takes entirely too seriously in his opinion. Nate stands on the other side of the room, eyes unfocused and staring off in to the ether. In that moment Dan realizes this is the first time they've actually shared the same time and space as the girl they have in common.

It shouldn't feel as awkward as it does, but he's not stupid enough to deny that he is clearly the other man on Blair's arm, platonic as they may be.

Eleanor waltzes into to room and he makes a beeline in the opposite direction, not feeling like being called Don, or what other incorrect variation of his name she chooses to use. He makes a right and a quick left and runs right into Jenny who immediately talks a mile a minute about the food, the drink, and everyone's clothes. Definitely loving to high life, he muses, and makes a mental note to somehow try to combat that later.

Hours pass and he's leaning against a wall idly sipping on some kind of fruity mix, tapping his fingers and wishing he knew anyone beside the hostess.

Speak of the devil when Blair comes from around a corner, a dramatic sigh escaping her lips.

"Always a wallflower Humphrey," she says folding her arms across her chest. "God you're just as bad as Nate."

Dan's eyes immediately shoot to where the shaggy haired blonde is standing pretty much in the same place as when he got here, which is odd, because Nate has known these people longer than he, and it seems strange that he's playing the social pariah too.

She wanders off again, and he's left contemplating why her boyfriend hasn't spent a single moment by her side the entire night. He himself had a few conversations with Blair in the few breaks she allowed herself from being the center of attention, but he can't think of a single instance seeing the two of them together.

It looks like Nate doesn't even want to be here and Blair can't be bothered in dealing with that, and he has no idea why they even…

He sips his drink and chalks it up to one of the many things he doesn't understand about the rich and privileged.

/\/\/\

It happens like this.

Dan is standing in Grand Central Station because mom has decided she needs to go to Hudson for the summer. To paint, she says, but he has a sinking feeling that it's more than that. He knows when dad is pretending that everything is all right, the last month of passive aggressive arguments the two of them thought they were getting away with, the look on his face is just screaming it behind a forced smile.

He feels Blair's hand on the small of his back, briefly forgetting they agreed to meet up here for that gala at the Guggenheim, as he watches mom walk away with her luggage in tow.

She knows the story behind the whole situation, his frustrations vented the second he figured out something was wrong, and doesn't comment on his silence once they part ways with dad and Jenny. Instead she just keeps her arm casually entwined in his the entire ride to the museum, and lets him have his rare moment of brooding silence.

It hits him then, how well she's gotten to know him, how comfortable they've become with each other, and that Blair Waldorf may actually be his best friend.

Yeah, didn't see that one coming.

/\/\/\

It happens like this.

Dan is sitting next to Blair at the breakfast nook of her father's summer house in the Hamptons, wiping sleep from his eyes and smelling the sweet scent of coffee. She pushes a cup in his direction without him even asking and he smiles graciously in return.

"Sleep well?" She asks without looking up.

"Goose down feels like it should be wrong somehow," he replies before taking a sip. "And yet I can't seem to care."

She actually laughs, vacation Blair seemingly not afraid to let loose without the prying eyes of Manhattan elite watching over her shoulder. Something he finds himself appreciating more and more as his two week tenure in the lap of luxury slowly winds down.

Fourteen days of random rich people tea parties, dinner events, polo matches, and discovering he's actually a little afraid of horses. Waking up never more relaxed due to expensive sheets, good coffee, and the fact that Blair seems really glad he came.

He watches as she nibbles on square cut pieces of cantaloupe, idly flipping through the paper, and wonders if they're going to do anything special for his last day or merely hang around the house watching old movies in the theatre.

She catches him looking and gives a half-smile before going back to the story she was reading and he knows it doesn't really matter what they do.

/\/\/\

It happens like this.

Dan is walking through Grand Central after spending the last week up in Hudson, checking his phone for messages and looking around for dad and Jenny who are supposed to be meeting him.

Mom's not coming home any time soon, something he figured out the day he got there, but it still makes him angry that she tries to pretend it's not her intent. Creative winds blowing or whatever lame excuse she tried to make for the fact that she left home in the first place and doesn't want to come back.

After narrowly avoiding a collision with some little old lady on one of those motorized carts, he spins on his feet and catches a flash of golden hair walking across the lobby. Nearly stopping in his tracks at the sight of Serena's clandestine return to New York, he fumbles with his phone to call Blair but she's not picking up.

Crap he thinks, remembering she has that thing with her mom today, the penthouse probably too full of people for her to notice the phone ringing.

He watches Serena walk all the way to the exit and swallows audibly, anticipating the fallout that's bound to come.

/\/\/\

It happens like this.

Dan is standing in the middle of Blair's bedroom with his arms wrapped around her while she cries big fat crocodile tears onto his shoulder. The fallout he expected from her former best friends return not nearly as big as the neutron bomb of secrets that went off right in her face.

Nate slept with Serena.

Nate doesn't love Blair.

And while she always suspected, always knew on some level, she never honestly expected them to do that to her. Dan can't say he's surprised. With Serena's disappearance and Nate's practiced distance it all makes perfect sense, the guilt causing one personality to shift and hide, the other to flee.

She's clenching at his shirt, the raw emotion pouring out of her in a way he would do anything to make stop. Putting a hand up to her hair, smoothing it up and down, he whispers promises softly against the strands. He'll never hurt her, or betray her, or lie. And he hopes beyond hope he can be man enough to keep them.

Still sniffling she pulls back to look him in the eye, hers still shimmering with tears, the intensity he sees causing his feet to shift. Pushing herself to stand on her toes she presses a soft kiss against his lips.

He blinks for a second, disbelief that she'd done it, words immediately falling from his mouth in attempts of explanation.

"We're having a moment Humphrey," she interrupts, hands still clenched in his shirt. "Don't ruin it by being you."

He blinks again, shaking his head and chuckling softly, wondering just how the hell this became his life.