A/N: All bolded quotes are from When Harry Met Sally. Sorry of blurry pre-series canon- I don't even know. Mostly AU. (Basically 10-08-05 doesn't exist in this story) Part one of a two part story. New chapters for some of my other stories are currently in progress.
Part One
August 26th, 2005
The first time we met, we hated each other.
No, you didn't hate me, I hated you.
Dan turns the corner of the penthouse foyer, and a tiny brunette collides into his side. Her eyes are glassy, red, matching the pout on her lips. Her nose wrinkles as soon as she takes in his appearance.
"Who the hell are you?" She asks, not bothering to hide her distaste.
She stands in a short ivory lace dress that hangs loosely over her thin frame. She doesn't seem to notice that she's still gripping his arm for balance.
Dan clears his throat, finds his posture straightening immaculately in her presence.
"I- I actually, I think I was invited by mistake," he stammers, and for some ungodly reason, doesn't remove his arm from her hand.
Her head tips to the side carelessly, "Well clearly. Who are you?"
"Dan. Dan Humphrey," he says.
"Humphrey?" She spits, brow furrowing. "Humphrey. Isn't that the inventor of cottage cheese?"
She seems fairly pleased with her jab as she raises a brow, challenging. He lets out a dry laugh and takes a breath to think of a response, but all he can come up with is, "I don't think they know who invented cottage cheese."
She props her foot up onto the small table and fumbles with her black garter, exposing her porcelain white leg. For a moment it's as if she's forgotten he was even there, and maybe she has. She drops her leg and looks at him again, rolling her eyes.
"You're still here," she says, "Why?"
Dan opens his mouth before closing it again. "I-" he starts, "don't know where else to go."
"You're not from around here, are you?" She asks, twirling a brown curl around her finger.
"I'm from Brooklyn, actually."
Snorting a laugh, "That really says it all, doesn't it?"
Something catches Dan's eye above her head and he sees Serena van der Woodsen leaning against the railing of the stairs, giggling while Nate Archibald whispers things into her ear. Her martini glass tips back against her lips and she swallows prettily. The brunette follows his line of vision and also swallows, but hers is slower, less controlled.
"Buck up," he squeezes her shoulder gently, "He's probably just reciting Anchorman quotes again."
When she meets his gaze again her face is much more stoic, an artificial smile gracing her lips as she says, "Get me a drink or get out."
September 7th, 2007
The second time we met, you didn't even remember me.
I did, too! I remembered you.
Blair carefully prepares her color coordinated folders for her Constance-St. Jude student committee meeting, placing all her plans for the winter formal into the blue folder, bathroom improvements in the purple, Ivy week in the yellow. She types rapidly in a text to Penelope about the Kiss-on-the-Lips party and rounds the corner, smacking into a stationary body. Headmistress Queller stands nearby, gasping at the collision. All of Blair's folders fall to the floor. The opposing side bends down to help her gather some of the papers.
She takes in the sharp jaw line, yellow shirt, sleeves pushed up, and that horrific red tie. There's just something so…
"Blair," Headmistress Queller trills, "This is Dan Humphrey. He's looking for extracurriculars to place on his college application and I thought it wouldn't hurt to add a St. Jude co-chair to the student committee. Dan's first in his class."
He looks down, blushing slightly. Blair rolls her eyes.
"Dan," the Headmistress continues, "This is Blair Waldorf, the current committee chair."
They're both silent for a few moments before he extends his hand to her and Blair takes it, letting his limber fingers cradle her small ones. He holds on for slightly too long. Blair yanks away and Headmistress Queller excuses herself, muttering something to Blair about "playing nice."
Blair doesn't understand Dan Humphrey; why he's here or what he wants or what he thinks he can possibly contribute to the student committee. Thankfully, he stays out of her way for the most part. He tells her this is his opportunity to observe how things work in the meetings, and she'd like to tell him that this is how things work in the meetings; her leading and him watching silently.
After the meeting, he follows her in stride through the courtyard, crunching loudly on an apple.
"We've met before," he says, not losing pace as they stroll. "Haven't we?"
Blair shrugs, gaze straight ahead. "I meet a lot of people. How should I remember?"
When she sits down at a table, Dan sits across from her, which is, well, annoying. He's examining her face like he's trying to place her existence in what she can only imagine is a dull and meaningless collection of memories. She's about to tell him it's rude to stare when recognition flashes through his eyes.
"Two years ago. It was at a party," he says, seemingly proud of himself for figuring it out.
She nods, "A party that, if I may remind you, you weren't invited to."
This causes him to laugh awkwardly and Blair is pleased. She likes him better when he's uncomfortable. The laugh subsides and is followed by a gentle silence.
"So you do remember," he says, voice soft.
She tilts her head, smiling. "Who could forget those hideous shoes?"
October 12th, 2009
The third time we met, we became friends.
"Medium black coffee, room for cream."
Dan reaches for the order, and as he does, a thicket of brown waves whips him in the face and grabs for the drink first.
"That's mine, actually," he says, trying for politeness.
"It's hers," the barista interjects quickly.
The woman turns to face him and he's met with Blair Waldorf's doe eyes staring back at him, a self-satisfied grin on her face. Her eggshell chiffon blouse is tucked into a pair of tight navy slacks and she looks much more mature than the girl he knew in high school. Her hair is lighter, longer. She looks less uptight, also.
He smiles back at her, "Please don't tell me we have the same coffee order."
"Please don't tell me that's how you're wearing your hair these days," she counters, taking a sip from the cup.
He laughs, running a hand through his longer curls and grabbing his drink when it's placed on the counter. She watches him in amusement, ignoring the phone that keeps vibrating in her pocket.
The leave the coffee cart and walk through campus, stopping every so often to tell a funny anecdote about their freshman years of college so far. Blair insults his outfit a couple of times, and he's amazed by just how many details about his ensemble she can point out. Blair exceeds at Yale, more so than Constance because she has genuine friends and connections. She realized early on that manipulation and power was not the way to make friends in college. When they get to her dorm building he clears his throat, filling the silence.
"Would you-" he starts, questioning his own words, "I know this is weird, but would you maybe want to go to a party tonight? It's a few blocks away, my roommate knows about it. Probably not your taste…but it could be fun."
She ponders for a few moments, Dan thinks merely to torture him, then she nods. "Sure. That could be fun."
x
Because she's Blair Waldorf, she catches him completely off guard. Dan and his roommate, Tom, show up her dorm to take her to the party and she looks absolutely nothing like she did when he saw her five hours ago.
She's wearing jeans. Like, since when does she even own jeans? But not just any jeans; jeans that look like they were custom made for her body, and her body alone. She bends over to grab her purse and Dan punches Tom in the arm to get him to stop staring.
Her shirt is another story. It's black, a silky material, and dips down in the front to reveal the slightest amount of cleavage. The whole thing reminds him of something Serena van der Woodsen would wear, and yet she appears very comfortable. Her outfits aren't as rigid and complicated as they were in high school, which makes him sort of sad. He liked the intricacies.
Then again, he doesn't mind the change either. Her hair is straightened, but tousled slightly and if he was being completely honest, she looks beautiful.
"Are you ready to go?" Dan asks, Tom nudging him in the side.
She nods, a wide smile on her face, and links arms with him before leading them out of the building.
