Note: The story now goes back in time, detailing the events leading up to the 1st Chapter.
It all began the night of Josh's party . . .
"Oh my God, Blair you look so hot in that dress"
"Do you think Nate will like it." Blair said twisting to get a good look in the mirror at the tight black dress she was currently wearing, "I feel like he's been pulling away recently."
At this Serena could only go back to re-examining the jewellery in Blair's box. Nate had been staring at her quite often recently, he'd tried to be subtle and do it when he thought she wasn't watching, but she'd definitely caught him a few times. She couldn't help but be flattered by the attention. Her and Natie had always had a bit of a connection. They were the lost souls of their little foursome. Blair and Chuck were the experts at scheming and tended to take life a little too seriously, always having some kind of goal or takedown up their sleeves, whereas she and Nate could always just have fun.
However, he was off limits, and she knew that. Blair had laid her claim on him the first time they'd all met. The two had been together ever since. They were Upper East Side's answer to a Will and Kate, ready to take the throne after uniting the Vanderbilt and Waldorf line. On paper they were perfect together, and Serena knew that her best friend saw Nate as her forever, but somehow she couldn't help herself but consider an alternative future, one where she got the happy ending.
"C'mon, you know Nate. The vacant stare is just his thing, I think he and Chuck just got a new batch of weed from that guy up at Clarence House," Serena replied attempting to alleviate Blair's concerns.
"Hmm, I remember them talking about it," Blair continued to examine herself running her hands down her sides to the hemline of her dress, "You're probably right, but I still don't think I can pull this off. I don't have the legs for it.".
Looking over at Serena, Blair could only envy the ease with which Serena was able to pick and choose her clothes. Everything looked fantastic on her, with her golden hair and legs that she had many heard guys say 'went on forever', in their awe-struck tones. As much as she would hate to be leered over by the male population, it was a fact of life that all girls need to know whether or not they are attractive. She was no exception. It certainly didn't help that even her own boyfriend was at times clearly entranced by her best friend. Blair could only be thankful that Serena was so pre-occupied by the rest of her male suitors to notice.
"No way, your legs are fantastic. Now go put on the Louboutin's I pulled out and I guarantee you'll have him eating out of the palm of your hand," Serena then turned to Blair and with a cheeky grin continued, "or any other place you want," aiming to make the conversation more light hearted.
Laughing Blair, grabbed a pillow and launched it at the now laughing blonde, "You have such a dirty mind,"
"Yeah, but, you love me anyway," Serena replied as she whipped out a flask to hand over to Blair, "especially considering I brought some of Chuck's finest."
"Why do I get the feeling that tonight is going to be mess," Blair said with a slight smile.
"You say messy, I say fantastic."Walking over to Blair, Serena put the flask in Blair's hand, "It's the last big party before Ivy Week and you promised you'd let your hair down this once."
Watching the smile grow on Serena's face, Blair began to drink.
Dan could only stare at little sister in disbelief as she scanned to room for her phone, preparing to go out, "I can't believe you are actually going to this party."
Jenny smirked at him, "You're just jealous that I'm invited and you're not."
Laughing Dan rose from his seat on the couch to hand pick up the missing device from beside the lamp, "Of course I am. I just wish that I was in your position, waiting hand and foot for girls like Blair Waldorf so I could attain such an honour as going to Josh Whitman's first party of the year," he said sarcastically, handing the phone over, "Is this what you're looking for?"
"Yeah, well, you wouldn't be complaining if it was Serena would you? Anyway, just because you live your high school life on the sidelines doesn't mean I have to." Jenny replied, as she grabbed her bag off the counter to put her phone in, "and thank you."
"Hey, it's a choice," Dan said choosing to ignore the Serena jibe, because let's be honest, he would happily serve her every whim if she asked him to. Unfortunately, she had no idea who he was, so even a discussion was off the cards. "I just don't get why you want to be her friend so much. She's only ever going to see you as the scholarship kid from Brooklyn. Trust funds and family legacies are the only things people like her respect, and I hate to break it to you, but we Humphreys have neither."
Looking at Dan exasperatedly, Jenny couldn't help but get annoyed at her brother's often repeated rant about their schoolmates. Even though she knew his heart was in the right place, she didn't think he was right. Whilst the Constance girls' had been a bit catty towards her, she knew that eventually she could earn their respect on her own terms, regardless of her family's lack of wealth. It wasn't about money, it was about proving you had power and the first step was to get in with Blair Waldorf. She just needed to show that she could handle anything thrown her way, and Jenny was right on her way to doing that.
"How many times do we have to have this conversation. I don't think they are all that shallow," however at Dan's sceptical look she did concede a bit, "Ok, most of them are, but not all of them. Anyway, I am running late and I think my cab's arrived so I've got to go." Jenny picked up her bag and jacket and made a move to the front door.
"Did you write, down the address of the place like Dad said?" Dan asked.
"Yep, it's on the counter. And I'll remember to text you when I arrive and when I'm about to leave," Jenny said, and she couldn't help but roll her eyes at her dad and brother's protective streak kicking in.
"Alright then," Dan nodded, as she opened the door, but then he called her back just as she was about to leave.
"Hey, hold on a sec," he said as she came back in. He couldn't help but be a little worried for his sister. He knew she was growing up, and if he hadn't before, the dress she was wearing plus the make-up definitely clued him in/ However, he still didn't think she knew what she was getting into with these girls and their parties. He'd heard many a story of the antics that would go on behind the closed doors of the seemingly mature and intelligent kids of Constance and St. Jude's, and he didn't want his sister to lose herself in all their drama. Where all the other kids had money, prestige and influence to fall back on, Jenny didn't. However, at the same time, it had been a while since he had seen her this excited and he didn't want to take that away from her.
"Just be careful. Have fun, but, please be careful too." Dan said sincerely.
Recognising the shift to a more serious tone from her brother Jenny responded similarly, "Trust me. I know what I'm doing. I'll be ok. I promise."
At this Dan nodded once again and watched as his sister walked out the door on her way to attend her first ever Upper East Side party.
Nate looked out over the edge of the balcony as he listened to Chuck bragging about his latest conquest, Emily Rogers, a hot senior who was also a strict Catholic and head of the chastity club for Constance. Supposedly she was quite the screamer.
He couldn't help but be jealous of his best friend. Chuck was able to do and get everything wanted and never had to think twice about the repercussions for his families like Nate had to. The 'precious' reputation of the Vanderbilt line was always on his mind and dictated his actions. Admittedly, it did suck for the Bass boy that he had an absentee father, but at least he was able to make his own choices, even if they did include persuading girls to break their promises to God.
Nate had been in a relationship with Blair for as long as he could remember. He'd always cared for her, but he knew in his heart that he didn't love the way he was supposed to. Especially at this stage in their relationship, considering the hints his mother had been dropping regarding the Vanderbilt ring. If he was truly honest with himself, he knew there had always been something holding him back from truly committing to the Waldorf heir . . . or someone to be more precise. Serena Van der Woodsen had always been able to capture his attention, from that first day in the playground when she'd wildly marched up to him demanding he go and talk to her best friend, the more quiet and composed brunette sitting on the swing she'd already claimed as her throne. For some reason, he'd never be able to get her out of his head, and it was about more than just her beauty. He didn't know whether to describe as careless of carefree, but one way or another, when he was around her he felt like he too could do or be anything he wanted.
A wolf whistle snapped Nate out of his thoughts, causing him to turn to Chuck in confusion.
"What was that about?" Nate asked
"2 o'clock," Chick replied, eyes focused, as he nodded in the direction of the entrance to the penthouse, "looks like there is some new talent."
There came a girl stepping out of the lift. Nate was pretty sure she was a freshman, he'd seen her amongst the fresh batch of minions Blair had attained as soon as the school year had started. He'd thought she was quite pretty initially, then she'd looked up at him with that adoring look that most of the keen fresher girls seemed to give him and the attraction had ended there, there was only so much desperation he could take. His best friend, on the hand, was much less picky.
"Freshman," he stated.
"Perfect," Chuck said smirking, as he downed his glass of scotch.
"You are despicable," Nate chuckled
Straightening his bow tie, Chuck replied, "Hey, not all of can be freaking monks. I guarantee once you seal the deal with Virgin Mary, you'll understand," before walking away
Nate could only shake his head as he watched friend begin to zone in on his target, "Seal the deal? Who says that anymore?"
Turning back around to face Nate, Chuck raised his arms and shrugging says cockily, "Guys who are about to get laid." With a wink, he resumed his journey through the crowd.