A/N: Alright so I don't even know how I feel about this idea yet, but I'm just gonna see where it takes me. This story takes place at the end of season 1 after Serena finds out about Dan/Georgina- minus Serena forgiving him and wanting to get back together. But the wedding happened all the same otherwise.

Please tell me what you think and feel free to make suggestions because I'm still playing with the entire concept. Aaaand I'm rambling, so please enjoy!

"Don't even think about it, Humphrey."

Her voice is icy cold and he has vague deja vu of a certain Thanksgiving when he saved a reckless blonde's life and found himself being yelled at by her tiny brunette friend.

Dan looks down at Serena laughing while tears stream down her face. On the exterior she seems happy, but he knows that she is utterly miserable inside and that it's his fault and this fact kills him.

"Blair, I'm just gonna bring her home to bed."

He begins pulling her up when Blair slaps his hand away,

"Honestly, you are the last thing she needs right now. What is wrong with you?"

He opens his mouth to speak, but realizes he can't find one solid answer.

He cheated on Serena. Serena van der Woodsen, the girl of his dreams, everything that is good in the world.

He cheated on her and he has no idea why.

At first he justified it as being because he thought she had cheated on him first.

But as time went on he realized it was a misunderstanding.

He didn't understand Serena, her values, her interests, her actions.

It may have been why he fell so easily in love with her, he was at a loss for flaws because he didn't understand her well enough to find any.

The way Blair is looking at him now, it feels like almost two years ago, at that Thanksgiving.

She had looked disgusted with him, as if he were the scum of the earth.

Maybe he is.

That thought is quickly erased when Chuck Bass approaches them.

"Humphrey, you heard the lady. I think it's time for you to leave," The combination of Chuck's raspy voice with his mischievous smirk are enough to make Dan clench his fists, "We'll make sure my sister gets home safe."

"Step-sister" he corrects under his breath. And then, "Fine."

He glances down at Serena one more time, who is now struggling to keep her eyes open and lets out a breath he didn't realize he was holding.

As he turns to leave the party he hears Blair mutter something that stings the entire way back to Brooklyn.

"You're pathetic."


Everywhere he goes, they stare at him.

It doesn't matter if he's in Brooklyn or UES, there's always at least three sets of eyes watching him walk down the sidewalk.

Slowly, he learns to ignore it.

He closes his eyes, takes deep breaths, and keeps walking.

It's not until he's looking through the sales rack at Bendels with Jenny that he sees her for the first time since that night.

Her hair is pulled back in a tight pony tail, all the make up is stripped from her face, a loose green dress hangs over her tan skin.

She looks very real in that moment- unlike the Upper East Side princess he used to fantasize about.

He quickly turns around and hopes she doesn't see him, but.. good god how immature can he be?

"Serena." His voice is low and she almost doesn't notice except she does and his heart immediately starts pounding against his ribcage.

Her eyes are soft, hurt.


He's thankful that Jenny is in the dressing room at that moment and not out here trying to salvage his relationship for him.

"Listen, I think we should talk sometime. About everything."

God he hates how much his voice is shaking when talks.

"Um," at least hers is shaking too. "Yeah. I would like that."

He takes a few steps closer to her- dating a van der Woodsen makes one very bold.

"Are you doing okay?"

"I guess I'm just sort of-"

Her soft voice is quickly cut off by,

"Humphrey, what the hell? Are you following us now?"

He watches as Serena closes her eyes with a small smile, because they've been in this position so many times before.

"I'm with my sister."

"Ew, you're both following us?"

Dan takes Blair in for a moment. Her hair in loose waves, skin lightly tanned from the sun, only a touch of pink lip gloss on her lips.

Apparently even Blair Waldorf requires less maintenance during the summer.

"I'm gonna try this on." Serena awkwardly flashes the dress and makes a dash for the dressing room.

Dan doesn't think he's ever seen her act so unsure of herself.

"We need to fix this."

Blair's voice is stern and don't even get him started on her eyes.

"Fix what?"

He lightly scratches his head and pretends to sort through hangers.

"Stop acting like you know anything about fashion and focus. Serena's a mess."

"I'll have you know that I got this shirt from Nordstrom in Hudson, not on sale, so I don't appreciate…wait, why am I having this conversation with you?"

Blair rolls her eyes and he notices immediately that her foot has begun tapping impatiently against the tile floor.

"It saddens me that you feel the need to brag about a shirt from Nordstrom. Although, doesn't surprise me…" her voice trails off slightly before continuing, "This thing, you and Serena being apart, it's not working for me."

Dan snorts out a laugh and waits for the insult, but nothing comes.

She just stares at him expectantly.

"Oh, you're serious," He watches her chin raise in what appears to be a nod, "I thought I was 'pathetic.'"


She tilts her head ever so slightly and Dan notices the light dusting of shimmer over her shoulders.

"You said that. The night of Penelope's party, as I was leaving."

Blair's eye brows furrow as if to remember the night clearly before she says,

"You thought I was talking to you? Don't get me wrong, Humphrey, you're nothing special. But I wasn't talking to you."

In that moment Dan feels an immense amount of relief, although he probably is pretty pathetic. Following is overwhelming confusion.

"Serena," she says lightly, interrupting his thoughts, "I was talking to Serena."

Dan can't even control the judgmental gaze that he lets fall on Blair.

He had cheated on her best friend, but he wasn't the pathetic one?

Maybe Serena was having trouble coping but 'pathetic' seemed like a harsh term to describe her.

"Stop looking at me like that," Blair snaps, "She needed a dose of reality. She was acting like an idiot and trying to go home with any guy who offered and I'd had enough of it."

Thinking about it, he assumes this is what Blair has done most of her life.

She's the dark dose of reality that wakes Serena up from her drug (or in this case depression) induced hazes.

"So you don't think I'm pathetic."

Just to clarify.


She takes a sip from her iced coffee.

"I cheated on Serena."

Blair glances up at him and a small smirk forms at the corner of her mouth,

"You thought she cheated on you first. It's not excusable… but perhaps understandable. You're like the plot of every romantic dramedy."

Dan rolls his eyes and leans against the rack of clothes, blinking at her a few times.

"And what do you want from me exactly?"

"I want to help you."

He's too shocked to say anything, simply waits for her to continue.

"It's become clear to me that Serena is miserable without you, and she's become the Serena that I used to hate- only more depressing. While you're not my first choice for her… You're her first choice for her."

"So why do I need help from you?" He can't help the edge in his voice, "If it's so clear that Serena wants to be with me, why do I need you?"

The sad thing is, which he would never tell Blair, is that he feels no emotion when he hears that he's Serena's first choice.

He's not overwhelmed with joy and relief as he thought he would be.

He's just apathetic about the entire thing.

"Because look at you, Humphrey." Her eyes travel up and down his body before continuing, "And try having a conversation with you once in awhile. It's infuriating."

"You never talk to me."

"And now you know why."

She spits back as she flips through the hangers in front of her.

"I'm going to have to teach you how to dress, how to act, how to seduce, etc etc."

"How to seduce? Blair, no. I draw the line there."

The devilish smirk on her face sends a wave of heat through him and he clears his throat awkwardly before almost tripping over a clothes rack.

"See? This is what I'm talking about. You're such a virginal non-virgin."

"Fiiiiine," he groans with irritation, "just don't get handsy."

Blair snorts a laugh and narrows her eyes at him,

"Why?" her voice drips as she brings a hand up to his chest and drags it down slowly, "You don't like handsy?"

"And I'm gonna stop you right there," He snatches her hand and returns it to her side. "If you think you can help me connect with Serena I'll gladly take the advice, but none of these games or manipulations."

Blair rolls her eyes in a huff and flicks her hand at him carelessly.

"Fine. Be here, Friday at noon. I'm finished with this conversation." As she makes her way to the dressing rooms Dan can't help but laugh,

"Nice talking to you as always, Waldorf."