He's not supposed to be here.

Looking out at the New York skyline, nothing but twinkling lights and shadow this high up, stray moon beams filtering in through parted curtains in a bed twice the size of his own. Bare skin barely covered by Egyptian cotton, head propped up by the remainder of a dozen down pillows, goose bumps freckling his skin from the breath of her sleeping at his side.

He's not supposed to feel this way.

The girl who once represented everything he hated about the privileged and upper class, whose sole purpose for the time he'd known her, seemed to be putting herself above anyone and everything.

The inclination to panic comes so natural, their already undefined relationship taking such a left turn, he almost wants to cut and run simply because he has absolutely no idea how to proceed from this point.

It almost feels like some kind of spy novel, though he's not sure who exactly is doing the infiltrating.

She shifts closer to him, mumbling something sleepily incoherent, and sighs contently when finally settled.

He's not going anywhere.


As if waking up in Blair Waldorf's bed wasn't awkward enough, (simultaneous thoughts of whether to just say good morning, was it good for you, or oh god, oh god, what did we do?) sharing a table at breakfast proves to be a challenge in itself.

Maybe it's the way Dorota eyes him with such suspicion, as if she somehow knows he's wearing the same clothes as yesterday, her protective streak akin to a mother bear ready to maul him dead should he prove to be like the other guys in Blair's life.

Or maybe it's the way Blair is so casual in her silk robe, showing enough skin to keep his eyes wandering, nibbling from a plate of fresh fruit and drinking orange juice from a champagne flute.

She appears to be completely fine with what happened between them. She isn't the one riding an introspective tilt-a-whirl over and over until she gets sick. It's only then he realizes she's waiting him, for his reaction, his answer to the question of where they go from here.

Knowing this somehow calms his stomach, enough to actually start picking at the croissant in front of him.

When she smiles, he knows he passed the test.


Almost making it back to the apartment without incident, the living room empty, and no one appearing in his peripheral vision, he makes a dash for the stairs when Jenny's voice stops him in his tracks.

Turning on his heels to come face to face with her and Eric, sitting next to each other at the counter with a plate of waffles between them, simultaneous smirks on their faces.

His babbling defense mechanism kicks into overdrive, (complete with manic hand gestures), and Eric looks confused while Jenny laughs knowingly.

Did you have fun last night?

The teasing way she says it is enough to send him back to the stairs without dignifying a response.

Getting out of the shower twenty minutes later, there's a text message from Blair.

Dorota approves.


Exchanging gifts is a surprisingly low key affair, despite the fact that he nearly tore his hair out trying to figure out what to get her. Did the new and improved Blair appreciate more heartfelt gifts? Or when it comes to material things does she still prefer the expensive and shiny?

He ends up buying her a first edition copy of Capote's Breakfast at Tiffany's, figuring he has a fifty-fifty shot of it being the right mix of pricey yet meaningful.

Her reaction is pure Blair.

The first thing she does is sniff it cautiously-God Humphrey what is it with you and smelly old books?-but the sarcasm doesn't quite reach her eyes as she runs her fingers over the text of the title. Realization that he's getting to know her so well, realizing that isn't such a bad thing.

She leans forward, kisses his cheek and murmurs thank you against his skin.

At first he's confused when she pulls out the mid-sized suitcase, something she notices and rolls her eyes at, before popping the locks open and presenting him with a pretty sleek looking vintage typewriter.

You want to be a real writer don't you?

He can't quite describe what it does to him (his heart somehow expanding a size or two), and must be silent for too long, because he can see her defenses going up. The anticipation in her gaze turns to a scowl, before he wraps his arms around her, resting his forehead against hers.

I love it.

She laughs softly, causing his eyes to shift down to see her smile, ruby red lips and brilliant white teeth.

Of course you do.


Meeting her dad isn't as bad as he (naturally) assumed.

A return trip to the ice rink because tradition is tradition, arriving a few minutes late (everyone and their mother chose to use public transportation today), he jogs up the path and spots the awaiting party.

Blair glares at him because she can't stand tardiness in general, let alone for an activity involving her father, and all he can do is shrug in apology.

Introductions are made-Daddy this is Dan, Dan, Daddy-and he's shaking hands matching a friendly smile. Not quite as polite when introduced to Roman, but apparently it's a lot more than the man got before.

Renting his own skates this time, ones that actually fit, gliding around the ice comes easier and he spends most of his time trying to keep up with Blair rather than having her guide him around.

She chooses Ice Capades Barbie look again, the outfit almost identical to the last one except for color.

Harold keeps up with them for a few laps before retreating to where Roman has chosen to watch from the sidelines.

Gloved hands hold each other firmly, all smiles and laughter as they skate, and this time he's the one who kisses her in front of all the happy people.

Later, when he's resting against the wall and Blair has gone off to get hot chocolate for everyone, Harold regards him curiously to the point of discomfort.

She's changed hasn't she?

It's a question that feels like it would take Dan hours to explain to him just how much.

She's happier than I've seen in quite some time, and I have a feeling you may have something to do with that, don't you Mr. Humphrey?

He couldn't possible take credit for what she's become. Hell they only became friends (and whatever they are now) because she's the one who did the changing. He's just an accessory after the fact.

Luckily Blair comes back before he can think of an answer and Harold just smiles at him when she situates herself under the crook of his arm and blows softly on her hot chocolate.


Part of him still can't understand how easy it is just being with her.

How sitting on the couch in the entertainment room of her penthouse, watching one of the old movies she favors, feels like the simplest thing in the world.

She leans against him, her head resting on his shoulder with one arm entwined in his, occasionally pointing at the screen in anticipation and explaining all the parts she loves best. He nods accordingly, being sure to retain the information she shares because he knows she expects him to love it all the same as her.

He wonders if it's going to be different when they get back to school. If they'll just fall into the old habits of studying, coffee, and texts without any of this sudden holiday affection.

The typical self-doubting part of him expects it to; always too damn insecure for his own good he fights every urge to just blurt out am I your boyfriend?

She squeezes gently at a particular romantic moment, and before he can help it, turns to place a kiss on her temple.

The way she slowly lifts her head to meet his eyes, a warm sweet smile spreading on her lips, before leaning in to kiss him is a good enough answer as any.


10… 9… 8…

It's a bizarre game of cat and mouse at the first annual Van der Humphrey New Years Eve party. The first time they've actually been in the same room as everyone else they know, has both of them playing social loner at opposite ends of the apartment.

Only slightly on purpose, the intent never to separate for the entire night, but when she pulls him into a shadowed corner (behind the odd shaped sculpture that will never make him understand art) and kisses him breathless before running off and talking with a few of Serena's cousins, it turns into a thing.

7… 6… 5…

Top of the stairs, he hears over his shoulder as she makes a quick pass behind the hors d'oeuvre table, and he tries his best to politely end a boring conversation with some of his Dad's old artists from the gallery.

He's been dodging Serena all night, (she knows, oh god she knows) but of course she chooses the moment he's about to hit the stairs to approach him all awkward smiles, and hey how's NYU? He replies as swiftly as he can, trying not to be rude, pointing to the stairs and muttering bathroom before leaving her there with a surprised pout.

Blair kisses him before he can say anything, throwing her arms around him-you're disgusting sometimes Humphrey-and laughs into his mouth.


4… 3… 2…

Funny how a little thrill can mean the world to her. The fact that he's willing to play, that he's not calling her out on the silliness, or moaning why can't they just tell people and be done with it?

Her eyes light up whenever they find a private section of an apartment just crawling with people, nerves on edge that they'll be caught at any given moment. The way Eric and Jenny have been eyeing them all night, just waiting for something to happen, or the fact that Serena doesn't seem to have any idea anything could possibly happen at all.

How his dad grins at him, but knows he can't say a word that a thing for stuck up rich girls just might be an inherited trait.

She admits in a whisper that she's actually having fun at a New Year's party, and damn him, she can't remember the last time that happened.

1, Happy New Year!

No hiding, no playing, no fear of social repercussion.

No clandestine meeting for the last remaining moment of a year wrought with changes.

Anyone with internet access, time on their hands, and a sick curiosity on the comings and goings of a select few Upper East Siders, knows they've been friends for months now.

She stands in the middle of the living room with hands clasped behind her back and right foot turned slightly inward. He can't help but a watch for a second, again trying to fully comprehend that she's there waiting for him with come hither eyes, silently telling him she is not afraid.

It's only a few steps but it feels as if they take days to reach her, arms going in slow motion as they wrap around her, the challenging lift of her brow as if he doesn't have the guts.

The balls drops as everyone screams, his lips closing the gap, toes curling at the way she sighs into his mouth as if they haven't been doing this all night. The kiss lasts longer than the traditional chaste ringing in the New Year, long enough to realize they're suddenly the center of attention.

Breaking apart slowly, sharing a reassuring smile, they turn and come face to face with their respective exes.

Serena stands there with a glass of champagne, eyes wide with mouth hanging open, as if this is the oddest practical joke that's ever been played.

Chuck (who Dan hadn't even realized was here) is a statue, arms folded, eyes threatening to stare daggers into each of them.

The shiny red panic button inside is flashing lights and blaring horns, and he can only think the fallout from the way they chose to expose themselves is only going to burn twice as bad for being so public about something so new.

Serena will be hurt that they didn't tell her, Chuck enraged that she was capable of being with someone without him knowing, and for the first time since it started Dan is not afraid about what might happen.

Without looking, he offers Blair his hand.

She takes it.