Summary:

This is an AU DS fic. Some of the facts from the show will be used, but Jenny does not exist. Dan has a twin brother named Brad. The events of this fic will parallel S1 and 2 with some slight changes.

The Lesser Humphrey: Prologue

10-8-05

Dan Humphrey hated his life. He hated the stupid private school his father was forcing him to go to and he hated being a twin. What was the point? It's not like they looked alike anyways. But, above all else he hated how boring and useless his life seemed. Granted he was only 14 and overly pessimistic, but he really had no choice when he was surrounded by a household full of merry sues. His mother always looked on the bright side of things, but there were times when he was sure that was all an act. She had the saddest eyes he'd ever seen on a person. His father was always preaching about positivity and auras and some such shit and Brad was so laid back that negativity wasn't even in his personal dictionary. He was everything Dan wished he had the courage to be: brave, good-looking, and likeable. Instead Dan was stuck with the short end of the gene stick. He was shorter, pale and dark-haired in contrast to Brads golden locks which were gift from their mother. Dan was also awkward and scared. Sometimes he felt like his fear would swallow him whole.

He sighed and put the book he was reading down and picked up the remote. He flipped through the channels while he made his usual running commentary. Brad stormed into the room dressed in a clean pair of dockers and a crisp shirt. He grabbed the remote and shut off the TV.

"Get dressed loser. I'm sick of your emo act,"Brad said firmly.

Dan looked up at his brother and said, "hey I was watching that."

"No, you weren't watching. You were mocking. Now get off your ass and get dressed. We're going to a party."

Dan rolled his eyes and said, "I don't go to parties. I'm lonely boy remember?"

"That's bullshit,"he said as he lifted Dan off of the couch and pushed him into his room.

Dan was not going to be forced to go to some ridiculous party with the children of vapid socialites who were even more vapid than their parents. So, instead he opened his laptop that his mom had bought him for his birthday and opened up his latest story file. He'd rather write something than be subjected to a painful and ridiculous attempt at socializing with people he hated. He was still sulking a half-hour later when his brother stormed into his room.

"Why the fuck are you not dressed?"

"Because I'm not going dumbfuck."

"What's your problem? No wonder you are stuck by yourself with no friends you refuse to get off your lazy ass and do something about it."

Dan was irritated. He hated when his brother got like this. Couldn't he just leave him alone.

"I have friends,"dan said defensively.

"Oh yeah. Like who? And Vanessa and Cedric don't count."

"Why doesn't Vanessa count?"he asked awkwardly.

"Cause she's a girl and a weird one at that."

Dan rolled his eyes, "that's illogical and there is a major fallacy in your argument."

Brad pointed a finger at him and said, "that is exactly why people don't like you. You say stupid shit like that all the time. Stop regurgitating what you read and talk like a normal person."

He knew that he was screwed and that Brad would keep bugging him till he went so instead of fighting with him over a dumb he decided to give in.

"I do talk like a normal person and fine I'll go on one condition."

"Name it."

"You never force me to go to another party ever again!"

Brad rolled his eyes and said, "you've got a deal little brother."

"You have a minute on me. Don't act like you're years older,"Dan replied as he closed the door on his face.

A quarter of an hour later, Dan was dressed and ready to go. Just as they were about to go their mom stopped them.

"Where are you boys going?"

"We're going to a party,"Brad replied.

She looked from one boy to another with a shocked look on her face.

"Okay you I understand,"she said as she pointed to Brad "but, Dan going to a party? Did you boys make one of your twisted bets again?"

The twins looked at each other and burst into laughter.

When they arrived at the Waldorf's Brad practically pushed Dan out of the elevator. He really didn't want to be here, but at this point he had no choice but to suck it up.

"Remember don't be a dork and have fun for chrissake,"Brad warned before he abandoned his brother to find his friends.

Dan milled around the place picking at the food laid out on the table. He grabbed himself a beer and settled on a couch in the corner. He took a sip and tried to look like it was something he did everyday when in actuality this was probably the second time he'd ever had a beer. He tried not to recall the first time he'd ever had a drink because it was a memory he would sooner forget. He found a snug couch in the corner that looked rather comfortable and took a seat.

"I probably should socialize or something," he thought to himself.

Dan got up and awkwardly milled around the room. He noticed a couple of guys from his AP English class and walked up to them

"Hey, guys."he said.

They turned and looked at him blankly before turning back to their conversation with saying a word to him. Dan rolled his eyes and muttered, "yeah nice to meet you too. Assholes."

Dan marched his butt back to his little comfort zone and avoided any attempt at talking to his classmates. He didn't understand what was wrong with them or if it was just him. His brother seemed to have no problem relating to these people. But, he refused to be nice to these uptight assholes that couldn't see beyond their own reflection. He took a swig of his beer and attempted to block out the idiocy surrounding him by playing a little game of Futuristic Divorce Court. It was a game he'd come up with last year when his dad had first enrolled him in private middle school. It consisted of trying to predict which one of his fellow classmates would end up married and then promptly divorce. IT was decidedly sick, but it amused Dan. He was so caught up in tyring to figure out which teen romance would implode in ten years that he didn't notice the vision that had plopped down next to him. He turned his head and his mouth nearly dropped open. She was a vision. All long limbs and golden hair. She turned to face him and reached out her dainty hands, "Hi, I'm Serena."

Dan felt a tightening in his gut. He willed himself to speak but all he could manage to do was take her hand and shake it vigorously.

"Whats your name?"

"Uh,Dan. My name is Dan."

"Nice to meet you dan. Could you let go of my hand you're hurting me."

He flushed red and awkwardly dropped her hand. "I'm sorry. I'm not exactly good with these sorts of things."

Serena giggled and said, "you don't like people?"

Dan tried to form a coherent thought but he was completely overwhelmed by the sight, the sound, the mere presence of her.

"I'm just shy."

"Oh don't be shy. Why are you sitting here all by yourself?"

"Its just easier."

"Well you're talking to me now. Its not that hard,"Serena said as she looked at him intently.

Dan debated whether he should tell her that she was pretty or if he should just continue with the small talk, but a small brunette pushed through the crowd and tugged on her arm.

"Serena I've been looking everyone for you."

She waved as her friend pulled her way. Dan sat there and watched her as she was pulled thorugh the crowd. He smiled softly to himself. Something had happened to him in that moment.

Later that night the boys sat at the island in the middle of the loft and talked about the party as they shovelled their way through two enormous bowls of icecream.

"See you had fun, right?"Brad asked.

"It was okay."

"If it was just okay, how come you have that goofy smile on your face?"Brad asked. He looked at his younger brother and it took a second before it clicked. "You met a girl"

Dan tried to hide his blush, but there was no fooling Brad.

"Who is she?"

"Its no big deal."

"Come on spill Danny-boy."

"Don't call me that. You know hate it,"Dan complained.

"Stop the evasive manoevers. Who is she?

"I don't know. It's the first time I've seen her. She's tall, Blonde. Her name is Serena."

Brad smiled and slapped him on the back, "I never knew you had that much game in you. You hooked up with the Van Der Woodsen."

"No, we didn't exactly hookup as you call it."

"Then what happened?"

"Nothing."

"Aww you have a crush. Be careful rumor is she squashes little boys like you like a bug."

"Shut up Brad."