This isn't completely AU (they're all exactly the same characters living in the Upper East Side), but you'll see from the flashbacks that all the relationships and friendships have been tinkered with to some degree. Anyway, feel free to tell me what you think and enjoy!
Present Day
"Drop everything you're doing. We're going shopping."
She heard him sigh on the other end of the phone. "As much as I'd love to witness you unleash your consumerist wrath, my essay for the Times won't write itself."
"Humphrey, it's tradition! You should know by now that the minute the leaves turn brown in Central Park, it's imperative that I replenish my wardrobe for fall!"
"Blair, it's hardly tradition when you were at Barneys two days ago."
"I am not going to repeat myself!" She proclaimed sharply.
Groaning, he picked up his jacket and slung his messenger bag over his shoulder. "OK, OK. Christ, I'm already halfway out the door."
"Good. Saks in ten. Don't be late!"
"You know, if you didn't break up with Serena, I'd still have a decent shopping buddy," Blair lectured, as she glided through the shoe department in Saks Fifth Avenue.
"I'm sorry if my love life doesn't revolve around Blair Waldorf," Dan said dryly, following behind her as though he were tied unto some invisible leash.
Blair shot him a cross look. "Well, it should! I need a girlfriend from time to time, you know."
"You still have Jenny," He offered sheepishly.
But she passed it off with a slight wave of her hand. "She's too busy securing her throne at Constance—as she should be anyway."
Dan let out a laugh. "I can't thank you again for morphing my sister into a ninety-pound, bon mot-tossing, label-whoring package of girly evil."
Blair rolled her eyes haughtily. "All she needed was a little nudge. Believe it or not, I always saw a little bit of myself in your sister." Then, she shot him a coy grin. "Maybe that's why you like me so much."
"Perhaps," He returned with a playful arch of his eyebrow. "The only downside is the fact that you constantly insist on bringing me to these shopping excursions."
"How many times do I have to remind you that shopping requires serious decision-making? And, if anyone's at fault here, it's you! You, Humphrey, are not exactly being useful."
"That's because you already look good, regardless of how many cashmere sweaters you decide to buy."
Blair smiled at him affectionately. "That's sweet, Dan. But you're still not off the hook. Now, tell me about this essay of yours. I'm guessing it's about a certain blonde Park Avenue princess?"
Dan nodded guiltily. "As tumultuous as our relationship was, it makes for good literature…"
Then, as though he suddenly couldn't take it anymore, he pulled Blair's arm so that she could properly face him. "But be honest with me."
"Always," Blair said, slightly jolted by the sudden gesture.
"Does that make me a horrible person? Me writing what Serena and I had just to get myself published?"
"Yes."
Dan's face crumpled, as another wave of guilt washed over him.
"But…then I remember you're my best friend, and I know that writing is your sick, twisted way of healing." She gave him a small grin, knowing that would be enough, and Dan found himself reciprocating the warmth.
"So what about you and that guy Nate then?"
Blair simply shrugged. "He's all right, I guess. We've only been on a couple dates."
"Seriously? But he's all you talk about," Dan said, furrowing his brow.
"Well, he's my only friend at Columbia, so who else am I supposed to talk about?"
Dan let out a chuckle.
"I still wish you studied at Columbia though and not in the fluorescent-lit lecture halls of NYU."
"And be around trust fund airheads everyday? I already have you for that, Waldorf."
Blair glared at him icily. "Four years. I've been your best friend for four years and this is how you treat me."
Dan winked at her. "Best part of our dynamic. Now buy the red dress. You'll look amazing in it."
Blair surveyed the red Oscar de la Renta dress on the hanger. "It would look good for the charity gala next week. Speaking of which, will you be making an appearance?"
"I'm not sure yet. But Jenny will." Dan quickly glanced at his cell phone. "OK, Waldorf. Fun's over. Got a deadline to meet. Coffee at the Met steps tomorrow?"
"Definitely," Blair beamed, giving Dan a final kiss on the cheek.
Four Years Ago
All around him milled well-dressed parents and their beaming progenies. It was the first Constance-St. Jude's brunch of the year and the Humphrey's were forced to stand awkwardly in the corner, away from the swarms of people who seemed to already know each other.
"See! I told you we'd fit in," Rufus Humphrey happily chattered, as he nursed a chilled mimosa on his left hand.
His son Dan shot him a look. "Please tell me that's sarcasm."
Rufus let out a soft chuckle, as though he had been expecting this kind of reaction from Dan all along. "Would it hurt to be a little more enthusiastic? This is one of the best schools in the city, Dan. You'll be able to follow your dreams now, get into a good college, and make a real name for yourself." Noticing the unconvinced look that remained on his son's face, Rufus let out a sigh. "Look, this past summer with your mom and me…it was a lot for you and your sister to take in, and I want to put that behind us; I want you to start this year on a good note."
It was the naked hope in his father's eyes that made Dan suddenly feel so ashamed of himself. Here he was, making their transition to a mom-free life even harder than it already was, while his dad struggled to hold everything together—their family, his marriage, and even his own sanity. And it wasn't like he was ungrateful for having been given the opportunity to go to St. Jude's. It was a great school. And it would prep him up for a good university. Ugh. He really was "Son of the Year," wasn't he?
Trying to shake his conscience of guilt, Dan looked up from his drink, ready to dole out some words of apology, when he noticed that his father wasn't even facing him. Instead, his gaze was settled on the brunette girl standing by herself next to the flower arrangements.
"I have an idea!" His father piped up in sudden excitement.
Dan inwardly groaned. This had "disaster" written all over it.
"Why don't you talk to that girl over there? You never know, she might be your classmate or something!"
Dan automatically blanched. Admittedly, she was cute, really cute. Her silky brown hair was effortlessly pinned up in a loose bun and the short, blue dress she wore underneath her blazer hit all the right spots—OK. No. Dan couldn't possibly be checking out another girl right now. Especially when his dad was bent on humiliating him at any moment.
"Honest to God, I'm perfectly fine right here, Dad," He asserted firmly, deliberately enunciating every syllable and word so nothing, absolutely nothing was lost in translation.
But his dad was clearly having none of it. "Go on! Humphrey's are supposed to be fearless!"
"No, we aren't! In fact, we're socially awkward and—" His muddled retort was cut short when his father practically manhandled him towards the unsuspecting brunette. Fortunately, his years of soccer practice had saved him the embarrassment of completely colliding with her, as his feet magically planted themselves on the ground. She immediately looked up at him, surprised and affronted by the suddenness of the whole thing.
"Hi, I don't think we've met. I'm Dan…Dan Humphrey." He tried his best to sound cool and placid but he knew for a fact that he was anything but. God was he a nervous wreck. It had only been—what? A good thirty minutes into this pretentious school function and already he had managed to make a complete fool of himself?
When her cold eyes subtly gauged his body head-to-toe, Dan was met with a sudden desire to crawl under a rock and never leave. It was either that or running up to his dad to launch into a thorough "I told you so!" speech.
When she still hadn't responded, her ferocious, brown eyes still boring a hole on his self-esteem, he latched unto the remnants of his so-called Humphrey fearlessness and forced himself to badger on. "You, uh, look like you're used to these things."
"Sorry?" She finally said, though her tone was cold and brash.
Dan nervously played with his tie, feeling his legs turn into mush. "You know, all these functions and mixers—you fit in well. I, on the other hand, don't." And then he snorted a little sloppily to hide his nerves. "I swear, if I have to listen to another string quartet play Mozart—"
"It's Debussy…'Arabesque No. 1,' if I'm not mistaken."
His mouth hung open. "Uhh…sorry?"
"And they're not all playing string instruments either," she droned irritably.
Dan suddenly felt a deep flush creeping on his neck. Abort. Abort. Abort. "Right…so you know a lot about…er, music?"
At first, she looked like she wasn't going to reply, like she was finally going to bring this ill-fated conversation to an end, so they both could return to their respective lives never to acknowledge each other again. But, to Dan's surprise, she let out a loud and impatient sigh and deadpanned, "I grew up listening to him. He's my favorite composer."
He was about to dole out his own response, when two preppy-looking girls suddenly slid beside the brunette whose name he still hadn't gotten.
"Blair!" They greeted in unison. Blair. That's her name.
The girl standing next to Blair was a straitlaced strawberry blonde and the other, a scowling, brown-haired girl. Like Blair, they fit in perfectly with the rest of the crowd.
"Hazel, Penelope" Blair drawled in greeting, not even bothering to look them in the eye.
"Who's your friend?" The blonde one asked, nudging the other with her elbow.
"Yeah, did he rob a polyester factory?"
They both burst into short, derisive laughter, as their eyes freely roamed his clothes with the same contempt Blair had donned just a minute ago. But just when he thought he'd be locked up in his vault of insecurity forever, Blair's eyes darted towards the sneering brunette and, in a calculated fashion, she countered, "So says the girl whose dress can be seen from space!"
Her words seemed to have carried the right amount of ire, as both Penelope and Hazel quickly hushed up in alarm.
"I—"
But Blair herself had already tuned out of the conversation. "Move along, Penelope. Before my eyes burst into flames."
The girls instantly scurried away with cheeks so red Dan couldn't help but let out a laugh.
"Uhh...thanks. You didn't have to, but…thanks, Blair." He decided he liked the way her name fell from his lips. It rolled off his tongue so easily, he was surprised he hadn't been saying it all his life.
Blair's gaze once again adjusted itself on Dan's face, but this time it was softer, with faint hints of amusement emerging from those piercing and enigmatic brown eyes of hers.
A small smile involuntarily lingered on his lips. She wasn't exactly the most inviting person, and her recent stunt proved that she had no qualms about hurting other people…but Dan, for all his rigid principles and affable tendencies, couldn't help but, well, like her. Suddenly, he wasn't too irked by his dad's bout of parental intervention anymore. In fact, he quite liked this feeling of delving into something new and unknown.
"Do you have a pen?" Blair suddenly asked, her pink lips twitching into a smirk.
Dan's face scrunched over as he began patting himself awkwardly in search of a pen, but the darn thing was M.I.A. For an aspiring writer, it sure was ironic to be bereft of the one thing he claimed to have a great hold of.
Letting out a genuine laugh, Blair suddenly closed the gap between them, until she was close enough for him to smell her sweet, flowery perfume. Dan was so caught off guard by the sudden gesture that his breath hitched in his throat. But unlike him, the close proximity didn't seem to faze the brunette one bit, as she boldly grabbed the pen he had foolishly forgotten about in his breast pocket, unscrewed the cap with her teeth, and pulled out his open palm.
1136 Fifth Avenue, Penthouse, she scribbled.
Dan furrowed his eyebrow. "What's this?"
Tucking the pen safely into his breast pocket and consequently earning another nervous gulp from Dan, she let out an easy smirk and said, "My address. Meet me there tomorrow at 2 PM sharp."
"Um…"
"See you then, Humphrey."
Still gaping, he watched as Blair walked over towards the crowd of guests. He was finally about to turn on his heel himself when, from the corner of his eye, he noticed her suddenly being pulled to the side by a set of diamond-embellished hands.
"Blair, sweetheart, there you are!" A frenzied woman in her mid-forties exclaimed. Something told Dan that the towering and deeply intimidating woman standing in front of her had to be her mother. Her eyes were the same shade of brown as Blair's and they sparkled with the same ferocity that made the hairs on his neck stand up.
"Mom, hi."
Her mother cast her a pleased smile, as she brushed a stray curl from Blair's face. "Now come along. Rose Farkas and the rest of the Colony Club want to see my new muse in the flesh!"
"Already? But the contracts haven't been drafted yet…" Blair's voice was so quiet and vulnerable that Dan was surprised this was the same girl he'd been talking to just a few minutes ago.
"Don't be silly, darling! Everyone's dying to meet the new face of my fall collection! And we, young lady, will not disappoint them." She shot her daughter a stern look, before sauntering away in a huff.
"Of course, mom. I'll…I'll follow you in a bit."
Dan watched as Blair's plastic smile faltered and then faded, when her mother was no longer within sight. His legs were already itching to approach her but, before he knew it, she shook her head, threw on a mega-watt smile and followed after her mother with all the confidence in the world.
Somehow, the whole thing just broke his heart.
