A couple of things: this is probably a three part story. I'll update as soon as I can. All the stuff that happened in the television series happened in this. I haven't taken the book into consideration. Also, whatever happened in the show happened in the guy's senior year.
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Welcome back, Upper East Siders. It's been a while, hasn't it? Five years to be exact. Five years during which some have travelled the world, some have gone to college, some have done what was expected of them and some have just done nothing. So, ever wonder where everyone is, right now?
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"Serena!" exclaimed Mrs. M, the oh-so-lovable Constance Billiard principal. Though the Five Year Reunion hadn't begun yet, Serena was already there. It was different experience for someone who was used to be twenty minutes late, to be twenty minutes early.
"How are you, Serena?" asked the principal, pulling away from the customary formal hug. "Your mother has been raving on and on about your success."
She shrugged. Was it success? A friend of hers had once describer success as the attainment of wealth. In that way, she was wealthy. Money had never been a problem for the blonde haired goddess, ever so often compared to Aphrodite. She was sure that she could stop working now and still manage to live a luxury life. Even if she didn't get enough money from her own career, her mother's divorce earnings were enough.
"Has she," commented Serena dryly. She didn't doubt that her mother would have gone on and on about her. Serena was everything Lily would have wanted to be when she was younger – successful, living without the continuous thought of getting married for money and without someone like Rufus Humphrey rolling over her shoulders. But now that Erik was happy in his second year of Brown, doing better than anyone would have thought, she had someone else to rave about too. "I think she's exaggerating. I'm not as successful as she thinks."
'How modest,' thought Mrs. M, smiling at the younger girl. She had heard about the success of the eldest van der Woodsen child for three years now.
"How is Erik?" asked Mrs. M. "I heard he's at the top of his class in Brown."
Serena smiled, fondly, at the thought of her younger brother. Her frequent trips to Rhode Island only increased their closeness, especially when Serena wasn't in the country, which was turning out to be quite frequently, too.
"He's doing great," she replied, "In fact, I'm coming from Rhode Island, actually."
"Oh, that's great." Mrs. M replied, nodding along. "I think more students are coming along, why don't you go meet some of your old teachers."
Serena rolled her eyes and headed straight for the bar. She could forget the awkwardness of drinking in front of her teachers, if only she had a vodka and cranberry in her hand…or two. She tapped her fingers against the bar, waiting for the bartender to tend to her instead of her chemistry teacher.
"What can I get you, Miss?"
She paused. As Chuck had put it, what happened to the Virgin Mary Serena who vowed never to take a drink again? Sardonically, she remembered last night. If she could do that, drinking was nothing.
"A vodka cranberry, double the vodka, half the cranberry," she ordered dryly, earning herself raised eyebrows from the bartender. But she didn't want to know whether that look was because of her drink order or the low cut dress her mother had insisted on her wearing tonight because she looked absolutely stunning in it.
And stunning she looked. Her wavyblonde hair was straightened for the night and fell softly to her back. Her big blue eyes shone, partially from the champagne she had swiped before coming here. Her face was a delicate rosy color, her lips were red and she looked the same as she had done during high school – absolutely gorgeous.
"Here you go, Miss," the bartender said, handing her the drink. She eagerly took a large sip, cringing as the vodka dribbled down her throat. Wasn't this familiar?
The Pre Boarding School Serena, as she remembered, knew this taste quite well. The Virgin Mary Serena had forgotten this taste. The High School Graduate Serena, however, knew this taste as well as Pre Boarding School Serena. It wasn't something she was proud of, but then again, she remembered the countless drunken nights all over the world, it wasn't something she would give up, either.
"Hey," the bartender said, sounding as surprised as he did curious, "Aren't you Serena van der Woodsen?"
She cringed. She hoped he wasn't one of the innumerable one night stands she had left the house of, early in the morning because that was one experience she would never like to relive.
"Yeah," she replied, nodding.
"Woah, I'm Jason Millerton…remember me?"
Honestly, she did not. So he continued.
"We went out when you were a sophomore. I was the swimming team captain…" he trailed off, waiting for the bulb to light up in her head.
And it did, but she didn't remember the times when they had gone out. She remembered the times when she had sneaked into the pool using the key he had given her.
"Right…" she said, nodding, "Well, how are you?"
"Great. I've been bartending for a while, went up to the Cape for a year. How 'bout you?" he asked, curious as hell to see what the once golden haired goddess of the Upper East Side was doing now.
"I travelled for couple years after school, got into the hang of going from one place to another and I started writing about it. I'm a travel journalist."
Nobody had expected Serena van der Woodsen to become a journalist, let alone a journalist about places where they didn't have electricity or water but she could safely say that she didn't expect herself doing anything less. She didn't know whether it was her constant restlessness that made her want to travel, or her constant need for excitement that made her leave a place after a month but it was the best thing ever.
"Wow, that's cool." Jason replied, "Are you still dating that Humphrey dude?"
Serena smirked. "We broke up after school. I'm off the dating scene for a while." Or try five years, she thought.
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Off the dating scene? That's not the S we remember but thanks to my still fabulous sources, I've discovered that the trip to Rhode Island to see Little Erik wasn't as innocent as she claims…
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Blair would deny, deny, deny if anyone asked her if she had become anything close to being predictable, or heaven forbid, her mother. But in the back of her mind, she knew that she had become predictable, and heaven forbid, her mother, when she went to the kindergarten school her daughter Audrey (who would've thought) went to and shouted at the teacher for letting her precious daughter play in the sand, effectively ruining the sun yellow dress her daughter was wearing.
Sometimes, she wondered whether Audrey was her child or Serena's. Because the five year old certainly acted more like her fun Aunt Serena than she did like her less-fun Mother Blair. Because of Blair remembered correctly, it was Serena who was out dirtying her sun yellow dresses in kindergarten while Blair perched on the bench with her legs crossed and sneered at her best friend.
Clasping the Tiffany & Co. diamond necklace around her neck, she stopped in front of her mirror. Five years, a marriage and a pregnancy hadn't changed her figure, much. Sure, she wasn't as petite and curvy as she had been but she wasn't fat, either. Her brown hair was curly, bouncy and wavy, quite like Serena's and her fox like eyes were getting older, tired and more stressed out, though.
She picked up the Cartier diamond studs from the vanity, pausing at the Swarovski encrusted frame with a picture of the happy family. Her daughter, currently sound asleep in her bedroom with the nanny, was wearing a pink sundress. Her husband, God knows where he was, was smiling fakely at the camera.
What a happy family they were.
She ignored the thoughts in her head and gave herself a once-over in the mirror before stomping out of the master suite and into the hallway. "Stella!" she shouted for the nanny, "I'm leaving."
The younger, pretty, obviously being fucked by her husband, nanny appeared in front of her. "Make sure Audrey has a good night's sleep. She's got a dance recital, piano and swimming lessons tomorrow. I don't want her to tire herself out for the dinner party I'm hosting later on. If my husband shows up, tell him to reach the reunion as fast as he can."
Stella nodded. "Yes, Mrs –"
"Oh, shut up," she snapped at the nanny before getting into the elevator that led down their 5th Avenue apartment building. The limousine was waiting for her, as usual.
She wondered what everyone was doing. Even when they had promised that they would keep in contact, this and that, during the graduation parties, none of her old friends actually kept in contact, with her at least. Serena was a given, though. The blonde stayed with them whenever she was in New York City. Nate and everyone else however, were just people she occasionally heard about here and there.
The driver stopped the car and she got out, looking at her old school building nervously. What if someone else was wearing the same dress? What if someone was more famous or successful than her?
"Hey, B," she heard the familiar voice.
She and Serena did the hugs and the kisses and the how are yous before they settled into the high school routine they had never left.
"Have you seen Kati?" asked Serena, snickering softly. "She's got four fucking kids."
"Are you fucking me?" asked Blair, smirking. "Wow, she must be as fat as a –"
"Whale, yeah, she is." Serena interrupted, finishing her fourth vodka and cranberry. "But don't mention it. Hazel said something to her and she totally burst out crying."
"Ouch," mumbled the shorter brunette, as they reached the steps into the school. "Shall we?"
"We shall." Serena replied, keeping her glass on the side of the steps. "Where's the husband, B?"
Blair shrugged. "Fucking the secretary, the assistant or probably himself."
She didn't know whether it was dark but a look of pure confusion, and sardonic amusement, crossed her face before it turned to the normal sympathetic. It wouldn't be empathy that would come from Serena, after all because nobody would ever dare cheat on her.
"Is he coming here?"
Blair nodded. "Unfortunately for us." She scoffed, looking around the whole place. "God, I don't even know why I married him."
You got pregnant, thought Serena.
"I would've been so much happier without him."
No, you wouldn't have, thought Serena. After all, it was because of her husband that Blair was who she was, the Editor of Vogue, the successful recipient of the Best Mother award which the Upper East Side unofficially gave out and the oh-so-happy woman which every girl wanted to become.
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Why so unhappy, B? Well, you know the Stranger You Married and funnily enough, so does S and everyone else. But are actually as unhappy as everyone thinks?
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Nate Archibald was probably the only one, he thought to himself, who hadn't done what he had wanted with his life.
He knew that Serena was a famous travel journalist who didn't stay in a city or country for more than a month. He knew that Blair was the famous successful editor of some fashion magazine or the other. He also knew that Chuck, with whom he had frequent contact, had taken over his father's company and turned it into an international empire. Those were plans which they had made halfway through school. Everyone in Constance and St. Jude's had an idea of what they wanted to do.
Except Nate Archibald. He knew what he was going to do, what he was expected to do, what he should do but he didn't know what he wanted to do.
But three years after he had done it, he knew that taking over his father's fallen empire wasn't something that he wanted to do. That didn't mean he didn't turn the fallen from grace company back on track. They were on again the firm for Eleanor Waldorf Designs. In fact, that was the first company he had signed on when he took over for his father.
"Daddy, Daddy," cooed a little blonde haired bombshell. "Mommy says she wants you dressed and ready to go in ten minutes."
He picked up the little girl, who had his hair and her mother's eyes. He didn't doubt that in the whole of New York, little Chelsea Kristine Archibald was the cutest child there was. Her blonde pig tails, big green eyes, she was the apple of everyone's eye. He had often heard people compare Chelsea to a younger Serena, who looked the same.
Serena, he wondered how she was doing.
"Shouldn't you be in bed, Princess?" he asked, picking up her up and walking towards the little girl's bedroom.
"Mommy said it was okay as long as I didn't fall asleep in Mrs. K's class tomorrow," replied the little girl, "Because Mrs. K doesn't like you and Mommy and she will take any opportunity to call you and Mommy to the school."
Nate chuckled. Trust his wife to teach her that. "Alright, but you better be asleep when we come back!"
"Okay, Daddy."
If someone asked him whether he was happy, he wouldn't know what to say. His job, although it was something he hated doing, was going well. They were finally back on track. His wife too was doing what she had always wanted, therefore she was happy. His daughter was a bundle of joy, also.
But were they happy?
He pondered, while taking out a tie from the closet. Sure, they had their fights but which family didn't? In the end, he knew that they were happier than most of the other couples in the Upper East Side. At least, he was sure that his wife wasn't cheating on him. And in the Upper East Side, if you're in a relationship without any adultery, then you're happy.
Rolling his eyes, he picked a blue and silver striped tie and went off to find his gorgeous, un cheating, wife.
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Well, N, you might not be doing a job which you wanted but unlike the rest of the Upper East Side, your wife isn't cheating on you…or is she?
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Vanessa Abrams hadn't changed her name after she had gotten married. If she could remember correctly, it was something to do with independence and wanting to be known as herself and not the wife of someone famous.
But the only bad thing about being known as Vanessa Abrams was that every woman in the Upper East Side thought that a certain Nate Archibald was free for grabs.
She smiled at her husband's name. It was a nice name, wasn't it? She could clearly remember the shocked faces of the crowd when they were getting married. Her husband's best man, Chuck, although slightly disapproving of the marriage was happy nonetheless for his best friend. Her maid of honor, surprisingly Serena, was happy too. But she had seemed a little bit distracted throughout the night. Blair, Dan and everyone else, however, remained shocked and awestruck. When they had started dating in high school, everyone thought that Nate and Vanessa were just a phase, like Nate and Serena. But turns out, as every invitee of the wedding found out, that it wasn't.
And to boot, they even had a little girl out of it.
Sure, getting pregnant right after school wasn't easy for either of them. Both were scared, nervous and absolutely terrified of dropping and breaking the baby but the up-side of having so many friends was that they were ready to babysit whenever the couple needed help.
"Hey, 'Ness."
Think of the devil.
She smiled and turned around, looking for his approval at the Jenny Humphrey original baby blue dress.
"Gorgeous." Nate replied, grinning. "Absolutely gorgeous. I'll be the luckiest man in the room tonight."
And old flare of jealousy came through, which every girl had felt during Constance. The luckiest man in the room would obviously be the one who went home with Serena van der Woodsen.
"You better think so," she replied, turning around to clip on her earrings.
Maybe Nate could be second luckiest. She looked at him through the mirror, frowning slightly. She knew that the job her husband was doing wasn't something he wanted to do or even liked but then again, she didn't understand the family agendas of the Upper East Side. Why wasn't in possible for a company to be passed down to anyone but the son?
Then again, she wouldn't know much about companies either. She let her husband take care of the company on his own while she did what she had always loved doing – making movies.
At twenty two, she wasn't famous but she wasn't unknown either. People knew who Vanessa Abrams was but they didn't go out and buy her short films, documentaries because she was Vanessa Abrams. She, however, was the youngest documentary maker to be nominated for an Academy Award.
It didn't matter that the nomination didn't actually work through because a much famous director gave his last minute acceptance to the nomination.
She focused back on her husband.
They were much happier than most.
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Happy, V? But if only a Lonely Boy could accept that, no? Don't fret, V, I'm not telling anyone.
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Daniel Humphrey would have done anything not to attend this five year reunion. He would've succeeded in staying at home and doing nothing if it hadn't been for his insistent, twenty year old sister who wanted to go to the reunion so much. Even after five years, he didn't understand the fascination Jenny held with the Upper East Siders.
He tugged at the tie he was forced to wear and looked behind the hanging mirror, into the loft. It hadn't changed much after his father had moved out of this place into the SoHo townhouse with Lily. They had come to a compromise, apparently because SoHo wasn't the Upper East Side and it wasn't Brooklyn either. Though, his father came to visit him and his sister ever so often.
He sighed, thinking how bad this reunion would go. It wasn't like he had kept in contact with whatever friends he had from school. The popularity he had gained from dating Serena van der Woodsen had died down as quickly it had started after they broke up. Again, he was back to being the nobody who once went out with the somebody of the some bodies. All the other people he had spoken to – Erik, Chuck, Blair and Nate ignored him like the blonde. He just the boy who had been dumped.
His one and only friend, Vanessa was still there, even though she was going out with Nate fucking Archibald.
His friend's relationship with the Prince Charming of the Upper East Side was something he would never understand and quite frankly, he had never bothered to understand either. In the back of his mind, he knew he would be lying if he said that Vanessa and Nate weren't happy but that didn't stop him from protesting to their marriage as frequently as he could.
That was probably the reason Vanessa and him weren't that close anymore, but like he had denied being in need of money, he denied that him and Vanessa weren't friends anymore.
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That's not what Mrs. Archibald is saying, Lonely Boy. Ooh, lookie here, here's Little J.
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Jenny Humphrey used to call herself a Serena van der Woodsen in the making. She had always looked up to the blonde, always wanted to be the blonde and it had once (in a time she would rather forget) become so bad that she was ten seconds away from stalking the blonde.
And now, she was halfway there. Her clothes line was more successful than she had thought, with little help from Eleanor Waldorf Designs and Nate's firm. In fact, she owed a lot to Nate's firm. She was partially happy, with the success of her clothes. She wasn't happy, however, with the way her brother was living off of her money.
Dan's writing career had gone down the drain, quite like his relationship with Serena. After a couple of articles published in magazines which no one read, he had stopped writing altogether and started living off of the money his father and Lily gave him and sometimes of the money which Jenny made. He would deny doing so but everyone knew it was true. Everyone also knew that nothing would happen so they just let it pass.
But enough was enough, thought Jenny, as she tied her Christian Louboutin heels around her ankles.
"Dan, let's go!" she shouted, standing at the doorway.
Maybe she could convince him to take a trip or something – rediscover himself.
A moment later, a ruffled and shabby looking Dan came into view. She rolled her eyes. She didn't even bother to tell him to tuck his shirt in. She wasn't attending the reunion for his benefit, was she?
No, she wasn't.
She was attending this benefit to smirk and snicker at all those people who had called her Little Jenny Liar throughout her four years of high school.
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You forgot to mention the other reason, J, something about N and love, right?
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Chuck Bass wasn't happy and he would admit it, live with it and then happily go and fuck someone else because he wasn't happy. His excuse to everyone around him was always the same and for some mundane reason, nobody ever said anything, not even his wife, except her.
He was Chuck Bass.
"Mr. Bass," said the nanny as soon as he walked into their fifth avenue penthouse. "Mrs. Bass told me to tell you to reach the reunion, immediately."
He nodded, dismissing her with a flick of his fingers.
Not many people were surprised with Blair got pregnant. It had been the summer when he had sent her off to Tuscany alone. She had come back with the news of her pregnancy. Obviously, his first thought had been an abortion. But Blair refused to that. They did the only thing Bart Bass and Eleanor Waldorf thought was acceptable – get married. They were married when Blair still had her figure. Nate was Best Man, Serena was Maid of Honor, their vows were utterly fake, on his part. Audrey was born a couple of months later. Nate was godfather, Serena was godmother.
He walked past the study, the kitchen and stopped outside the hallway, pushing his daughter's room open softly. She was sound asleep on the queen sized bed, her hands under her head. It was a picture to be seen, he thought with a smirk because not only did his daughter look gorgeous, because Chuck Bass was getting sentimental.
Two things had been able to get emotional ever since the birth of his daughter, he realized, his daughter and her.
"Mr. Bass," said the housekeeper, speaking quietly when he was shushed by his boss. "Mrs. Bass called twice. Miss van der Woodsen called once, also."
He nodded, brushing Audrey's head. "Alright."
Ten minutes later, he walked out of his daughter's room and into his own. Blair had already put out the clothes she wanted him to wear, which was an elegant Armani suit. He snorted, throwing them away and walking into his closet. She would never take out his clothes for him, he thought with a smirk. Nope, she wouldn't be angry if he decided to walk into today wearing nothing with his customary scarf.
He smirked when he remembered that she had his scarf.
He took out the clothes he was going to wear and quickly changed, walking out of his room. He kissed his daughter on the cheek, causing her to stir and quickly whispered good night before leaving the penthouse like he had entered.
Giving his wife a call, he pressed 3 on speed dial.
"Chuck Bass, where the fuck are you?" the familiar Blair Waldorf-Bass hissed.
He smirked and decided to walk to the reunion rather than taking the limo, like she would have. "I'm coming Blair."
"Get here quickly, everyone's wondering if you're even coming."
"I wish I wasn't." Chuck replied before ending the call.
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Let's divulge into C's phone, shall we? He has six speed dials. Number 6 is none other than N. Number 5 is his secretary. Number 4 is his company advisor. Number 3, as we've seen, is B. Number 2 belongs to his daughter's personal line. But, who's Number 1 in your life, C?
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Basically, it's five years later. Whatever happend in Season 1 happend in thier senior year. After that, they graduated.
Enjoy!